back-to-school giveaway from jcp!

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Olsenboye belted print dress and foldover tote (c/o jcpenney) | Lucky Brand Emma ballet flats (Marshall's)

Even though my classroom days are behind me, I think the back-to-school season is the perfect time for a fresh start. I still feel a little gravitational tug toward retail during this time of year, and when I think of back-to-school shopping, I get butterflies in my stomach. There’s nothing better than those early August sprees and picking out the perfect school supplies and first day outfit. I still stock up on colorful pens, day planners, and cute notebooks, and I’ve replaced new backpacks with new messenger bags that will fit my Macbook, and lunch boxes with reusable coffee cups.

I was in elementary school in the 90’s, and floral baby doll dresses were my mini-fashionista apparel of choice. I usually paired them with keds and matching socks. Annnnd, probably a matching scrunchie or two. Oh, and usually shorts underneath {mandated by Mom} so as to remain modest and respectable while playing on the monkey bars during recess. Did I say mini-fashionista? Maybe in training. This Olsenboye belted print dress seemed like the perfect grown-up version of my old favorites, and a great transition piece for summer to fall.

Second chances are along the same lines as fresh starts, no? I love second chances. If you missed the first jcpenney giveaway a few months ago, you have another shot! They’re offering up another $50 gift card to a lucky APP reader, just in time for back-to-school!

Here’s how to enter: 

Leave a comment with your best or worst back-to-school style memory. Be sure to include your email address or URL so I know where to find you if you win. 

That’s it! You have until this Sunday, August 21st to enter. All entries must be received by 11:59PM EST.

What Do You Think?

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124 Comments

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  5. Rachel wrote:

    The summer before sixth grade I finally was allowed to get my ears pierced, and I wore a pair of black and purple dangly heart earrings that were quite hideous in retrospect, although I loved them at the time!

    Posted 8.21.11 Reply
  6. Hollie wrote:

    I was in junior high in the late 80’s and used to rock a gigantic Swatch watch on my leg!

    Posted 8.21.11 Reply
  7. Deanna G. wrote:

    My worst style memory was probably sophomore year in high school. I thought it would be really cool to wear heels but I never wore them before & I looked like a total dork. I was wobbling around all day.

    Posted 8.21.11 Reply
  8. kim wrote:

    I use to always wear windsuit in the bright colors. so ugly!

    Posted 8.20.11 Reply
  9. kim wrote:

    I use to always wear windsuit in the bright colors

    Posted 8.20.11 Reply
  10. twoteacups wrote:

    Oh dear, my worst back-to-school memory was wearing flare dark purple sparkly pants in 2001. I don’t know why I decided to buy these, they were hideous, didn’t really fit properly and WERE PURPLE. They never really matched any of my shirts so I always paired them with a black shirt and it looked really bad.

    Posted 8.20.11 Reply
  11. Adele S wrote:

    In elementary school I used to wear an outfit that consisted of matching cotton shorts and a shirt, which were made from perfectly matching floral cotton fabric. For some reason, it was the thing to wear during that time. Now when I look back at those outfits, I’m horrified! The 90s sure did have some odd fashion options. :D

    Posted 8.19.11 Reply
  12. vanessa wrote:

    I remember dressing up for the first day of school – it’s just a special day and there’s always the first-day-of-school pictures :)

    Posted 8.19.11 Reply
  13. Khadija wrote:

    My worst back to school memory was going into the 5th grade (as if you’re not awkward enough at that age) with a real coconut head haircut courtesy of my dad. Oh was that mortifying.

    Posted 8.18.11 Reply
  14. Jo wrote:

    One of my worst memories was my Grade 2 school picture. I looked super cute, but my collar was rumpled and I didn’t notice. Needless to say, when my mom saw the photos, she was mad. I learned by carrying a mirror to picture day from then on.

    Posted 8.18.11 Reply
  15. Kelsey wrote:

    In 2nd grade my best friend and I came to school in the exact same outfit – teal and black striped leggings with a turquoise sweatshirt that had a puppy face on it. Everyone made fun of us and called us twins. Apparently our Mom’s were best friends as well and shopped at the same place! :)

    Posted 8.18.11 Reply
  16. Lianna wrote:

    Denim Overall. Enough said. Oh middle school…How I don’t miss you EVER.

    Posted 8.18.11 Reply
  17. Jessica wrote:

    Super tight paisley printed corduroy pants were my first day of school outfit my senior year of high school (it wasn’t long enough ago for them to be actually stylish)…I had just started dating my now husband, and he still talks about how outrageous those pants were AT LEAST once a month

    Posted 8.18.11 Reply
  18. I don’t particularly remember getting new outfits for back-to-school. Though I do remember having a great pink polka dot bag for my first day of kindergarten, and I kind of wish I still had it…

    Posted 8.18.11 Reply
  19. sleepyheadedmom wrote:

    My worst back to school fashion memory was when I started 7th grade (starting junior high, new school and all) and I decided to grow my bangs out. I should have started earlier but whhen school started I had those weird bangs that you couldn’t do anything with. Of course school pictures are taken at the beginning of the year so mine was horrible. I had my bangs pinned or clipped to each side and it looked super frumpy. I have not had bangs since because I’ve always feared “what if I decide to grow them back out?”.

    sleepyheadedmom at gmail dot com

    Posted 8.18.11 Reply
  20. Megan wrote:

    In middle school I left the tag on my jeans on the first day of school… the tag with the size on it. That sucked.

    Posted 8.17.11 Reply
  21. i always hated back to school shopping when i was younger because finding jeans that i liked was always such a battle i’d try on like 50 pairs and only end up getting 1 or 2 of them maybe.

    holliister at gmail dot com

    Posted 8.17.11 Reply
  22. Laura wrote:

    I had this interesting outfit from The Limited that I wore first day of sophmore year. It was sort of a jumpsuit with a skort. It had a great blue/green print, but overall it was pretty awful.

    Posted 8.17.11 Reply
  23. Megan wrote:

    OH, I remember it well…pink and white striped collared shirt, under a white long crewneck sweater. Top it over a long pink sweater skirt, with a layer of white THEN pink socks, before I put on my white booties to complete the look. I wore plastic, Cupie Doll earrings, with my home permed hair in a banana clip and the FROSTIEST pink lipstick you ever-did-see!

    Yes, the 80’s were good to me… :)
    mom2orsini at comcast dot net

    Posted 8.17.11 Reply
  24. Lynda Del wrote:

    Well, on my first day at a new middle school there was a strict dress code in which no shorts were allowed to wear except for during Phys. ed. I wore a pair of culottes which is similar to a skort but was considered unacceptable because it looked too much like shorts and was sent home the first day.

    Posted 8.17.11 Reply
  25. crys142 wrote:

    in 4th grade I got a Julie Andrews pixie cut. I looked like a boy the first day of school :(

    Posted 8.17.11 Reply
  26. Worst school memory was in 6th grade, going back to school after getting my hair cut a few days prior. The stylist gave me bangs but because my hair is wavy, my bangs curled all the way up! It was like a spring! I didn’t know what to do so I hairsprayed my bangs straight until they grew out!!! pmgiglia at yahoo dot com

    Posted 8.17.11 Reply
  27. My worst fashion memory would be going to school in the 6th grade with super short, unflattering, boy cut hair! And braces. Ouch. My fashion did nothing to help out because I was still wearing bibbed overalls. Corduroy bibbed overalls none the less!

    Posted 8.17.11 Reply
  28. My best back to school outfit was in 7th grade when we came back to school from winter break. I had gotten a furry white winter coat for christmas and i wore that ALL day. I thought i was so cute and cool cause furr coats were the rage! however, they served chili dogs for lunch, and lets just say darn kid who tripped next to me at lunch and spilt his chili dog all over my WHITE FURRY AWESOME COAT. :/ :) lol

    Posted 8.17.11 Reply
  29. Jen wrote:

    I went to private so my memories surround loafers. Ugly oxfords and penny loafers that I had to wear all the time with my uniforms. I always hated those shoes! And to this day I avoid all styles that remind me of them.

    Posted 8.17.11 Reply
  30. Aly K wrote:

    Picking out my first day of school outfit was always my favorite when I was younger. My mom used to make us wake up early that day so that she could take a million pictures of me and my brother before we left for school. It’s fun to look back on all of our first day outfits now.

    Posted 8.16.11 Reply
  31. Tanja wrote:

    My worst back-to-school memory is thinking I was hot stuff in my neon colored socks (that matched my neon colored shirt and shorts) with my white Keds. My hair was a disheveled ponytail. All this was because I thought I was grown and could adequately dress my self. *cringe*

    Posted 8.16.11 Reply
  32. SWFTerra wrote:

    80s elementary schooler here. Interestingly enough, we had a JCPenny in our small town right downtown. I remember doing a lot of school shopping there. I’m actually pretty sure that’s where I got my first bra. Shhh.

    Anyway, I remember I had this really great cranberry pencil skirt with, what I thought was, the most badass patch with an airplane or something on it. I used to wear it with a cropped black & white mottled sweater and tights. That was my fancy look in 5th grade. :)

    Posted 8.16.11 Reply
  33. Isabella wrote:

    Keira, I am with you on the pretty pens! I’m a college student and I buya pack of purple pens at the start of each semester because they seem to make whatever written task I have to do much more exciting.
    Recalling my worst back to school memory;
    With my parents’ limited income, back to school meant stocking up on an assortment of t-shirts from Wal-Mart, most of which had stupid phrases or pictures ironed on the front. In the seventh grade I picked up a baby blue tee with the word “adorable” in big bubble letters. This adorable was written in rainbow colors, and the very first time I wore it all the kids teased me, insisting I must be homosexual to wear rainbow colors….Gosh, seventh graders are dumb. But I was still hurt, and never wore that shirt again!

    Good luck with the APP shop,
    Isabella, Msmaafu@gmail.com

    Posted 8.16.11 Reply
  34. Kat Gosney wrote:

    When I was going into 5th grade, my mom bought me a Nike shirt that said “beat by a girl? get used to it!” and I loved it. I didn’t like most of the clothes my mom bought me, but that shirt was great!

    katlovesjeremy@gmail.com

    Posted 8.16.11 Reply
  35. Katelyn Yeager wrote:

    I was going into 8th grade in 2003 and I thought I’d try to go for a punky look. I had recently bought these plaid pants. I wore them with all the confidence in the world till a boy told me that we weren’t allowed to wear pajamas to school. I was mortified that he actually thought I wore my pajamas! Needless to say I didn’t stay a punk for long!

    Posted 8.16.11 Reply
  36. Sherry wrote:

    I think one of my best back-to-school outfits has to have been the very first: red plaid pleated skirt and mustard-coloured turtleneck – with a little navy Winnie-the-Pooh logo on the chest – documented by the obligatory first-day-of-school photo taken by my mom as a send-off! Suddenly I wish I still had a plaid skirt in my closet …

    Posted 8.16.11 Reply
  37. Jamie Lynn wrote:

    Side ponytail. Every day.

    Posted 8.16.11 Reply
  38. shopfreak wrote:

    Best school memory: Senior year of high school
    Worst: Changing schools before sixth grade. Thanks for the chance to win!

    Posted 8.16.11 Reply
  39. HB wrote:

    i used to wear my hair in a high tight ponytail off to the side. on the first day of school i’d tell my mom… put my hair high up on the side! ha! and that was my fancy hairdo!

    mydiaryofasimplelife.blogspot.com

    Posted 8.16.11 Reply
  40. Carrie wrote:

    Hair crimping. That’s enough!

    Posted 8.16.11 Reply
  41. Mallory wrote:

    Well, I went to private school so unfortunately I didn’t get to pick new back to school clothes, but it seemed like every year meant a different hairstyle. The worst had to be in 2nd grade when I was trying to grow my bangs out and my mom decided to perm them [just the bangs not the rest of my hair] so they would stay out of my face. I looked like I had a giant Brillo pad on my forehead. ahhh!

    Posted 8.16.11 Reply
  42. Anonymous wrote:

    When I was 13 and 14 I had this short lived obsession with lime green. Ew. On the first day of my freshman year, I wore lime green pants (a slightly subdued shade of lime but still ugly) that were from the women’s section and really didn’t fit right, with this blue/purple and green mosaic flowered shirt. The shirt and pants kind of went together but then I decided to add my new belt that I was super excited about and dying to wear. Unfortunately, the belt was bright pink, yellow, and blue with cats on it. It was horrible. I cringe when I see those photos. And there are several photos, because my two best friends and I hung out after school that day and had a parent take a bunch of photos of us. I was also kind of in the midst of a bad hair stage at that point too. Ew.

    Posted 8.16.11 Reply
    • Amy G. wrote:

      Oops, forgot to add my name to that above post about the green pants and non-matching belt.

      Posted 8.16.11 Reply
  43. Kimbercrafts wrote:

    Most of my back-to-school outfits in elementary school consisted of a corduroy jumper layered on top of a floral turtleneck and saddle shoes!

    http://www.kimbercrafts.com

    Posted 8.16.11 Reply
  44. Lory wrote:

    In first grade for picture day, I was wearing a blue sweater tucked in and I was rockin’ suspenders. I was also wearing boat shoes. My mom topped it off by giving me a side ponytail. Oh the 80’s, you gotta love it. But I have the say, the suspenders were my favorite part! :)

    w.patterson1@yahoo.com

    Posted 8.16.11 Reply
  45. Lindsey Smith wrote:

    My best back to school memory was on my first day of senior year. Since I went to a small school, everyone was laid back so I wore jeans and a basic light brown fitted v-neck tshirt. So comfy! I still have the shirt 4 years later! :)

    Posted 8.16.11 Reply
  46. Ash wrote:

    gotta love wearing head-to-toe, purple American Eagle as I entered high school. just slightly embarrassed by that one. :) arkodet(@)gmail(dot)com

    Posted 8.15.11 Reply
  47. Love the dress! And I feel the same way about back to school season.

    Posted 8.15.11 Reply
  48. Love that outfit!!!! Pennies has the best back to school deals…I love to shop fir my kids there!!!!

    I remember my outfit for the first day of sixth grade (I think) it was the eighties…I wore black stirrup pants (aaaaaaaaaaaaah! Look they were cool at the time!) with this black and white crazy print button down and some kind of strange black belt…hair teased at the bang of course! On that first day back I felt like a little mini Madonna….looking back, it wad hideous!!!!!!!

    Posted 8.15.11 Reply
  49. Heather wrote:

    As much as I love clothes, hands down the best style memory was uniforms. Best 8 years of my life! Everyone wore the same thing and you didn’t have to worry about it!

    Posted 8.15.11 Reply
  50. Ellie wrote:

    School clothes were always stressful (not a fashionable child!), so my favorite back-to-school was the year I went to a school with a uniform. No fuss, no muss.

    Posted 8.15.11 Reply
  51. rebecca wrote:

    oh geeze! i have two older sisters and every year my mom got us matching outfits. i thought it was pretty cool to look like them but i dont think they felt the same way!
    rwvanvoorhis at gmail dot com

    Posted 8.15.11 Reply
  52. Alexis wrote:

    Middle School. My mom bought me boy polo shirts which I saw on a boy at school (!) and wouldn’t let me shave my legs. Not a good look for a young lady.

    Posted 8.15.11 Reply
  53. heidi wrote:

    this is so fun, thanks for the giveaway! i remember wearing a cute plaid jumper in second grade that my mom made me — definitely a good fashion memory!

    Posted 8.15.11 Reply
  54. jeanette wrote:

    Worst memory: Flashdance style sweatshirt with leggings and a spiral perm with crispy bangs. Enough said.

    Posted 8.15.11 Reply
  55. Valerie wrote:

    Double socks (where two socks on the same foot, with the top one showing above the other one.) were fashionable when I was in school. I wanted to wear them like all the other girls, but my mom said no because she thought it was ridiculous (and probably not worth the extra laundry).
    However, she did manage to find single socks that mimicked the slouched double sock look and bought them for me. Thanks mom!

    Posted 8.15.11 Reply
  56. jackie wrote:

    5 years in a row, i wore the same tight dark red tank top with sunflowers on it for the first day of school. no sure if that’s my best memory, or my worst, but at least i knew my taste, right? i took what i knew and ran with it.

    Posted 8.15.11 Reply
  57. I have alot of best memories, but my worst has to be when my Grandma made me and my Brother matching, polyester, bell bottom outfits, with our names on the front! (Sorry Grandma). She tried and I love her! I didn’t appreciate her sewing skills back then, but now I wish she could make all my clothes, tailor made for my taste and proportions. I do have a picture of the two of us in that outfit, roller skating no less…….Hmmmm…..if I could only find it of course I would show you ;)

    Posted 8.15.11 Reply
  58. My best back to school memory was when I started high school, and I had just come back from a shopping trip to the Mall of America with one of my friends. I felt like a rock star in my new clothes!

    Posted 8.15.11 Reply
  59. Lindsay wrote:

    I don’t why I thought this was in, but I always wore oversized sweatshirts turned inside out with leggings… it is hard to look at the pictures!

    Posted 8.15.11 Reply
  60. Jennifer Pasour wrote:

    My favorite back to school memory was from elementary school when I got my hair cut short to look like Kim, the pink Power Ranger, which was all the rage while I was in the first grade. I remember thinking I was awesome with my new haircut!

    Posted 8.15.11 Reply
  61. hethomas wrote:

    I went to Catholic school and I absolutely LOVED my black and white saddle shoes in second grade.

    Posted 8.15.11 Reply
  62. Sarah wrote:

    I remember tight-rolling my jeans and then layering two pairs of scrunch socks over the top. I could never get my jeans rolled tight enough for my liking, but thankfully my friend, who was dropped off at my house every morning before school, was excellent at tight-rolling, so I didn’t have to suffer the humiliation of going to school with too loose jeans.

    Posted 8.15.11 Reply
  63. Sarah wrote:

    I remember on the first day of ninth grade I wore suede boots…in the Florida heat. Looking back, I have no idea what I was thinking, except that I was a trendsetter!

    Posted 8.15.11 Reply
  64. Jen wrote:

    best back to school memory has to be senior year of high school when i was FINALLY allowed to drive to school and park in the parking lot. my school had a small parking lot so only seniors were allowed to drive/park. it was the best feeling – being top dog! haha

    Posted 8.15.11 Reply
  65. Kate wrote:

    favorite: school supplies. mmm, yummy. i love everything about them, right down to the smell of the crisp white notebooks and fresh erasers.

    least favorite: pictures. on the first day of school, my sweet, well-meaning mother would make us pose with one hand on the door and the other clutching the backpack so cooly slouched over a single shoulder. lawdy, i suppose those were the good old days?

    Posted 8.15.11 Reply
  66. Anonymous wrote:

    I had a really sort boyish hair cute. And one year for pictures I had to wear this really girly outfit along with. Not my highest moment. O well. College has lead to some better dressing.

    Posted 8.15.11 Reply
  67. Anonymous wrote:

    In 5th grade I wore a magenta, short-sleeved, mock-turtleneck with black polka dots and shoulder pads. Shoulder pads in 5th grade. Yikes!

    Posted 8.15.11 Reply
  68. Kate M. wrote:

    Back to school memmories…ahhh! My mom was also one of those parents who would make my sister and I pose and she would take our picutres on the first day of school. So (un)luckily I have all of these great outfits documented. Worst: floral leotard (the one with the snaps on the bottom, yep) and black leggings with stirr-ups..god who invented those things?? Best: for 1st grade I wore a white dress with a cartoon character that matched my lunchbox..you can tell I am super happy with my outfit in the pictue :)

    Posted 8.15.11 Reply
  69. Andrea wrote:

    Oh how I loved back to school shopping. My Grandma would take me to Lamonts :) My fave thing in like 3rd or 4th grade was OVERALLS. I remember how awesome I felt when I got a pair of white ones and wore them with pride all year.

    Posted 8.15.11 Reply
  70. My “Scariest” back to school memory has to be when I moved the United States from Colombia, South America. I spoke absolutely no English! The school looked huge compared to my small private school I was used to. The teachers talked and talked in class and I couldn’t understand anything. Many of them really thought if they spoke slowly and loudly I would understand them. I only had one defense mechanism … nod and smile.

    Lunch was tough. No friends, no language, no nothing. I couldn’t even order food.

    To this day, I am amazed of how far I’ve come to. It wasn’t easy but I know it is doable. Now a days, I teach Spanish as a foreign language. I can relate to my students and I can sense the concern, excitement and anguish of learning a foreign language.

    Posted 8.15.11 Reply
  71. Megan wrote:

    Platform foam flip flops on the first day of high school and a tiny t-shirt with “ROXY” spelled out across my boobs in rhinestones. Horrifying!

    Posted 8.15.11 Reply
  72. My best back to school style memory was back in 1981. I was starting high school & I
    wanted to look ” totally wicked” (sorry, 80’s slang). I searched the mall for an awesome
    outfit and found it in a pinstripe, form fitting, bright turquoise jumpsuit with padded shoulders
    and tapered legs. I paired this look with white & gold open toe sandals, big gold dangling earrings and lots of long, teased hair! Although this ensemble would be incredibly tacky now, it is
    a pleasant memory because I felt so good about myself that day!

    treneebarker at hotmail dot com

    Posted 8.15.11 Reply
  73. Heidi wrote:

    Colored turtleneck under a cartoon sweater with colored jeans (that of course matched the turtleneck). Oh the horror!

    Posted 8.15.11 Reply
  74. christina nguyen wrote:

    bowl cut + uniform for 13 years!!!

    i can’t wait for my first day of college / freedom to wear whatever i want for school!!!

    Posted 8.15.11 Reply
  75. Ashley D. wrote:

    Not necessarily a “back to school” style memory…just a middle school style memory. I remember how awesomely cool it was to cut the foot out of a sock, roll it and use it to create a bun with your hair. I, along with all of my friends, wore our hair like this for most of 6th grade. I can’t imagine putting a sock in my hair now! LOL

    Posted 8.15.11 Reply
  76. Lauren wrote:

    I remember my first day of third grade and I was in a new house and new school. I got off at the wrong bus stop and then stood outside crying until some nice samaritans took me inside and called me Mom.

    Posted 8.15.11 Reply
  77. Shealyn wrote:

    Well I didnt have any crazy outfits (we wore uniforms) but on the 1st day of my ninth grade year I tripped and fell……..in front of my sis and her friends who were all seniors…..I was (and still is..haha) a clutz.

    Posted 8.15.11 Reply
  78. Jessica L wrote:

    I remember wearing my favorite daisy dress on the first day of class in elementary school. It was so cute and bright and sometimes I wore it with black lace sneakers and tennis shoes!

    Jessica
    lab.jessica@gmail.com

    Posted 8.15.11 Reply
  79. Shelbel wrote:

    Remember those big, poofy bangs? I have way too many school pictures featuring those.

    Posted 8.15.11 Reply
  80. I don’t remember a specific outfit, but I do know that I ALWAYS dressed way too warmly on the first day of school. After my parents would buy me new fall clothes, I couldn’t resist wearing them! :) suspyle@hotmail.com

    Posted 8.15.11 Reply
  81. Sage wrote:

    For my first day at a new high school, I wore head-to-toe beige! I don’t know what I was thinking. :)

    I still buy school supplies every fall too! I loved my Lisa Frank Trapper Keeper in elementary school.

    Posted 8.15.11 Reply
  82. lyndsay! wrote:

    I feel the same way. I still love back to school season!

    http://craftanista.blogspot.com/

    Posted 8.15.11 Reply
  83. Christina wrote:

    When I was in 6th grade I went back to schol shopping a K-mart and I saw these cool jeans. They were acid washed and they had boxers at the top so it looked like your pants were sagging. I begged my mom to buy them and she did. And I NEVER not one day wore these pants I was too afraid that I couldn’t pull it off.

    Posted 8.15.11 Reply
  84. Every year I wanted to lose weight over the summer and come back and WOW everyone with my svelte figure. That never happened. But, on the plus side, I would always rock a great first day of school outfit! My favorite was the year I saw this plaid skirt with over the knee tights in Seventeen magazine and I bought the exact outfit at Sears and rocked it hard the first day of school. : ) Oh, the 90’s.

    Posted 8.15.11 Reply
  85. Emily wrote:

    Two words: white pants. It was the first day of my sixth grade year and you can guess what showed up along with me. Another year the zipper on my pair of jeans broke and I had to hide it all day with a belt. And in elementary school, I rocked a bowl cut. I am full of fashion mishaps.

    Posted 8.15.11 Reply
  86. Linda Z wrote:

    I hope the deadline is the 21st?

    In Kindergarten I wore a navy dress with little red yarn bows in my hair… it was so cute and classic. :)

    Posted 8.15.11 Reply
  87. Meg wrote:

    So I’m not sure if this is a best or worst back to school outfit memory, but it’s amusing none-the-less.

    When I was a kid, my mom was a HUGE fan of hand-me-downs. At the time, I didn’t mind them, because they were still new clothes to me, which I always thought was exciting. I distinctly remember my first day of first grade outfit. It was a hand-me-down, plaid dress with a little white collar. But my favorite part was the buttons on the collar…three different buttons in the shape of a pencil- each a different color. Now, fast forward about 20 years and I’m now a teacher. My first year teaching Kindergarten, there was a little girl who had on the EXACT same dress. Her mother must have believed in hand-me-downs as well…and it almost made me wonder if it was the same one I’d worn that had somehow made its way into her hands! If it had been any other outfit from my childhood, I probably wouldn’t have noticed it, but something about first day outfits really stick out in my memory and made this partticular outfit stand out:)

    Posted 8.15.11 Reply
  88. julie wrote:

    In keeping with the fashion theme, I remember the first day of my 10th grade year choosing to wear denim Levi’s shorts, tennis shoes, and an Adidas t-shirt. My how my style sense has changed … Perhaps I need to win this to even further improve on my standards. The good news about that day was I left early to go get my learner’s permit. I probably drove myself to the mall and bought more sports wear. Lame.

    Posted 8.15.11 Reply
  89. Sarah Schreiber wrote:

    oh boy. these blue, green, brown, and white striped pants with a white cami and lime (more like snot) green half-cut hoodie. it was truly horrible. oh, and bright white strappy sandals. oh, elementary school….

    sar.schreiber@gmail.com

    Posted 8.15.11 Reply
  90. Ok, this isn’t MY story but it just happened yesterday and I really pity this kid. I work in a salon and we’ve had a ton of back-to-school haircuts coming through but yesterday took the cake. A mother came in with her son, who is going to his first day of middle school TODAY and said she wanted his hair “frosted and feathered”. The stylist who took care of the kid asked him if he wanted his hair that way and he said he didn’t care. The mother kept saying she wanted his hair to look 80’s but she didn’t say why. I have a feeling that kid is going to end his day stuffed into a trash can or a locker.

    Posted 8.15.11 Reply
  91. T Crane wrote:

    I remember my mom putting my hair in sponge rollers the night before the first day of school. I looked like Shirley Temple!

    Posted 8.15.11 Reply
  92. Caroline wrote:

    My white t-shirt with a monkey on the chest. The best part? It had a flap that could be opened to view the contents of the monkey’s mouth – he/she was chewing a banana.

    Definitely the coolest kid on the block.

    cmichelson714 [at] gmail [dot] com

    Posted 8.15.11 Reply
  93. Sonja Zupevec wrote:

    back to school shopping of course! i loved getting new clothes for the school year :)

    Posted 8.15.11 Reply
  94. Stephanie Wilson wrote:

    My best back to school style memory involved my first pair of Guess? jeans. I grew up in a middle class family like most of America and the price tag of Guess? Jeans prevented me from getting some. So I was stoked when I was given permission to not only get a pair but also a matching Guess? T-shirt and socks. I’m pretty sure my jeans even had the little zippers. I wore them as often as I could and cried when I outgrew them. My love of Guess jeans has never faltered.

    Posted 8.15.11 Reply
  95. Pamela wrote:

    Tight bike shorts, big oversized t-shirt, equally big scrunchie in a side ponytail. Right, and don’t forget the white Reeboks (with the straps!).

    Classic, no?

    greatwhitetee@gmail.com

    Posted 8.15.11 Reply
  96. Jessica S. wrote:

    I started a high school where I knew nobody with gigantic banana bangs. They were so terrible. I started to pin them back and grow them out that week!

    Posted 8.15.11 Reply
  97. I’m pretty sure I thought overalls and pastel pink eye shadow with giant sparkles was stylish at one point. I shudder… But I would love me some JCPenny gift card money! Fingers crossed!

    Posted 8.15.11 Reply
  98. Anonymous wrote:

    My mother made me wear a spruce green plaid jumper for my first day to middle school and I was so embarrassed. I stopped letting her pick out my clothes at that point!

    meandthebeastloryn@gmail.com

    Posted 8.15.11 Reply
  99. Paola wrote:

    I attended a catholic school therefore uniforms were required, the only thing I could really style was my hair which I hated! I had really freezy hair and one time my mom cut my hair so short I had a triangular afro!

    Posted 8.15.11 Reply
  100. Keely wrote:

    I did the jersey knit dresses and leggings with different colored socks on each foot. All accompanied by my purple scooter or banana seat bike. It was the best!

    http://www.casualchickiki.com

    Posted 8.15.11 Reply
  101. Lisa S wrote:

    cute pictures! i love back to school as well from the new supplies to the new clothes. hmmm… I went to elementary school in the 80’s so it was probably all bad but i think the worst may have been the overalls I wore freshman year of high school. I shudder to think of it but back then I thought I was hot stuff. :) memories!

    Posted 8.15.11 Reply
  102. Jaime wrote:

    Beige floral leggings with stirrups at the bottom

    Posted 8.15.11 Reply
  103. Jenn wrote:

    I didn’t hit my growth suprt until college, so I was one of the shortest people in my grade all throughout school. I yearned for Gap jeans — like all the other girls were wearing — but even the shortest pair was inches too long … so I wore Gap Kids jeans until I graduated! Should have just went with dresses and skirts, like I do now! ;)

    Posted 8.15.11 Reply
  104. Liz wrote:

    My favorite out was probably my kindergarten outfit. My mom even helped me coordinate my backpack to my outfit.

    Liz
    26 and Counting
    http://twosixandcounting.blogspot.com

    Posted 8.15.11 Reply
  105. Going back to school always was my favorite time of year. It means my birthday is coming up, volleyball season, and sweatshirt weather!

    Posted 8.15.11 Reply
  106. I always loved going back to school – nerd, I guess. I remember one year my Mom took me on a surprise back-to-school shopping trip where I picked out a purple sweater with green and white argyle around the neck. I loved that sweater – even wore it for pictures that year. It really complemented my way too short and curly haircut Mom gave me that year…ugh.

    Posted 8.15.11 Reply
  107. I’m not sure if this is best or worst, but it’s definitely a favorite memory. Every day on the first day of school my dad would line up all of the kids and take photos of us & our outfits, so we have a whole collection of photos ranging from kindergarten to high school. It’s pretty cool to look at the changes. When I was in college, I even continued the tradition!

    Posted 8.15.11 Reply
  108. Joann wrote:

    When I entered 6th grade I got an outfit from the mall…I actually think it was JC Penny…instead of from Wally World. I remember feeling so pretty and in-style for the first time! :)

    (Until Sunday, August 14th to enter???)

    Posted 8.15.11 Reply
  109. Mami2jcn wrote:

    I was raised by a single mother and in the 4th grade I remember going to school with clothes we bought at a garage sale. They were really outdated and I felt really self-conscious about it.

    Posted 8.15.11 Reply
  110. Kimberly wrote:

    Definitely back to school shopping!

    Posted 8.15.11 Reply
  111. Lucy wrote:

    Think the dress Madeline wears…. yup, that was my uniform for seven years with saddle shoes! The funny thing is now peter pan collars are all the rage – I practically saw my old uniform on a girl walking down the street the other day! So funny!

    Great giveaway!

    Posted 8.15.11 Reply
  112. Kait P. wrote:

    My mom had about 30 different pairs of mismatched spandex shorts/leggings and spandex tunic-type things for me when I was young and they were every shade of florescent out there. And no, this was not trendy at the time (or ever!).

    Posted 8.15.11 Reply
  113. Diane wrote:

    I went to Catholic School for my first 8 years,but I remember going to buy new crisp white blouses and new shoes,a new jumper if warranted. Then off to buy all the pencils,paper etc. I remember always starting after Labor Day so you had ALL of August to enjoy.
    Now,I am the teacher and just yesterday bought some things for my room. A new timer,new bell,some new resource books for Math and a vocabulary learning center for learning all those 6th grade Math terms more fun.
    Yes,I too,bought some new clothes and shoes. I still get butterflies the night before even though now I have the BIG desk! I start August 30th for meetings the September 1st is the big day!
    I enjoyed this post very much. Great idea to reminisce about school days!
    Always,
    Diane

    Posted 8.15.11 Reply
  114. A bowl cut, floral leggings (with stirrups), and a matching floral long sleeve shirt. That was my outfit in my first grade school picture. I also had chicken pox and was missing a tooth or two. Such a funny thing to look back on… I love how much innocence and “carefree-ness” those kind of looks display. :)

    Bonnieingettysburg.blogspot.com
    Bonnie830@comcast.net

    Posted 8.15.11 Reply
  115. Elizabeth wrote:

    Oh my, I remember a polo shirt that was like a giant flag paired with some red shorts. Also most likely with white crew socks up to the mid-calf and my coveted K-Swiss tennis shoes! I thought I was so stylin’! Aww those were the days…

    Posted 8.15.11 Reply
  116. jwolfe06 wrote:

    Oh, this is easy. My mom used to make me wear leggings with stirrups on the bottom. SoOoOo uncomfortable! My favorite? Overalls. Hands-down.

    Posted 8.15.11 Reply
  117. Jessica C. wrote:

    Two words: bowl cut. I thought it would be super stylish for my first day of grade two. It wasn’t. My polyester blue striped pants and matching long sleve polyester turtleneck made matters worse. But my school photo from that day is still good for a laugh!

    Posted 8.15.11 Reply

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