keiralennox.com and related social media accounts may contain advertising and affiliate marketing links from ShopStyle; I earn a small commission for clicks and/or purchases of linked items. keiralennox.com is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to amazon.com.

Any gifts or services that brands/companies send to be featured on this blog are clearly disclosed as “Courtesy Of” or “c/o” in each applicable post. All views and opinions are my own, and if I wouldn’t use/purchase a product or service myself, I won’t feature it on the blog. Because friends tell each other the truth. Cool?

My Grown-Lady Shopping Rules

02/18/2019 87 Comments

My Grown-Lady Shopping Rules

02/18/2019 87 Comments

Editor’s Note: This post first appeared on the blog on 9/10/14, and it’s one of the more popular posts in the archives. It’s more than 4 years later, and although I’m older and more established these days (i.e., more disposable income for clothes and accessories) I still stick to these ‘rules’ when I’m shopping, and it’s completely changed the way I think about stocking my wardrobe.

I love looking back on these posts of ‘yore, and I hope you do, too! 

Since the day I learned to dress myself, my style M.O. was to “look cute.” (I’m not saying it was always successful; there was a very unfortunate oversized JNCO jeans phase in my adolescence). Now that I’m getting older, that’s shifted to “look polished/sophisticated/put-together.”

A year ago, I purged my closet of all the bad shopping decisions of my twenties. It was one of many closet cleanouts; I’d spent years in a cycle of buy-wear-toss and couldn’t figure out why I was never satisfied with my stuff.

During that Labor Day 2013 Purge to End All PurgesI got the moment of clarity I so desperately needed: the trick wasn’t filling a wardrobe with a whole bunch of random inexpensive stuff; it was creating a well-edited collection of great stuff.

For so many years, I equated good style with having lots of options and never wearing the same outfit twice. So I bought as much as I could within my [limited] budget: I rummaged through clearance racks, shopped at outlet stores and fast fashion retailers, and gave zero damns about quality or fit. I wasn’t invested in my clothes because I tied their worth to their value; which wasn’t much.

After that last cathartic closet cleanse, I promised myself that going forward I would be much more mindful of what I purchased. And I have been. In the last 12 months I’ve completely changed the way I think about shopping and my style: I have a better grip on what works for my body, I’m not afraid to splurge on quality basics, and I understand the value of keeping things super simple.

Here are the self-imposed rules I’ve followed to create a closet that I really love on the same budget I’ve had for years:

1. Is it on the list? One of the things that’s helped me the most this year is keeping a mental list of the pieces I think are missing from my closet from season to season, and sticking to that list when I’m shopping. The benefits are two-fold: it keeps me from buying a bunch of random stuff, and helps me keep an updated inventory of what I have.

2. What’s it made of? When you start to pay attention to garment construction, you can easily spot shoddy pieces that will fall apart after the first wash. Now I check the tags on clothes the same way I check nutrition labels on food: I won’t buy shoes or handbags unless they’re leather (I always have great luck finding both on Hautelook), and I try to find things made from natural and/or durable fabrics that are easy to care for, like cotton, lyocell and rayon.

3. Does it fit? No seriously, does it fitNot to be confused with, “can it zip?” Here’s what I’ve figured out as a 5’3″ hourglass: as much as I love shift dresses, I’m much better off in tailored and wrap styles; curvy-fit jeans that sit higher on the waist are my friend; super tight skinnies and cropped pants of any kind are my worst enemy; I should avoid mini skirts and shorts with less than a 4-inch inseam; and I feel best in tops and sweaters with some breathing room. Once you figure out what’s most flattering for shape, shopping becomes so much easier!

4. What’s the cost-per-wear? Five years ago, if you handed me a $100 gift card, I’d buy as much as I could with it, supermarket sweep style, and end up with a bag full of things I’d probably only wear once or twice. Now, I’d put it toward a staple — a great leather jacket, a pair of classic black suede pumps, or a little black dress — that I can wear lots of ways for years to come. At the end of the day, it comes down to cost per wear. If I impulse-buy a clearance top for $20 and wear it twice, my CPW is $10. If I splurge on a versatile black romper for $80 and wear it 25 times, my CPW is around $3. So romper, FTW.

It took me a while to get over my obsession with more is more, and realize that it’s better to have a few pieces I really love than a lot of pieces I just kinda like.

5. Will it play well with others? When I’m shopping for clothes, I stick to mostly neutral tones and pick just a few printed statement pieces. I used to do the exact opposite, and I ended up with a closet full of mismatched patterns and colors that didn’t work together. Now I can easily remix my favorite pieces and put outfits together quickly.

Keira Lennox

I'm a small town lady from the sunshine state with an affinity for bookstores, beauty counters and unfussy style. I spend my days running my flower shop, and my nights blogging about what I love and what I wear.

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  • Simone 02/19/2019 at 10:14 pm

    Love this post! Great tips for all!

  • Sarah Winton 02/18/2019 at 12:47 pm

    These are such great rules to shop (live) by!


  • juniper9173 07/17/2017 at 6:08 pm

    Great ideas! I have only in the past year found the styles that work best for me and I’m definitely having to watch the age thing as I just turned 44. Yikes!

  • […] As a florist, my every day basics include skinny and/or boyfriend jeans, denim shirts, t-shirts, shirt dresses, and flats; but when I stocked my closet exclusively with these things, and a business networking event or dinner party with friends popped up on my calendar, I would commence to panic with that age-old crisis: “I HAVE NOTHING TO WEAR!” Then I would run out and buy something last minute that I didn’t really love and would only wear once, and over time, my closet became a mish-mash of too much stuff that didn’t work together, and lather, rinse, repeat. The cycle would’ve continued forever if I hadn’t purged all the excess, approached my style with some intention, and laid down a new set of shopping rules. […]

  • […] of my Grown-Lady Shopping Rules is making a list of the pieces I’d like to add to my wardrobe each season. I scour style […]

  • […] thing down to a science. Last year, I nailed down my top 10 wardrobe essentials, gave myself some ground rules, and got serious about shopping with intention. Now, I don’t have to think about it; I can […]

  • One In One Out | Keira Lennox 01/07/2016 at 6:29 pm

    […] in a new era of mindful consumption, I haven’t needed any intense de-cluttering. But while I shop with intention and carefully consider most purchases, I still fall into retail therapy traps and have, um, […]

  • manorgreen 07/31/2015 at 5:08 pm

    Great rules – I really need to follow them more often!

  • stolenbysara 07/31/2015 at 12:39 pm

    I obey the same rules and I’m all for cost-per-wear. As we grow older it’s definitely important to invest in quality pieces with great cuts and that are more timeless! stolenbysara.com

  • alcaspar 07/30/2015 at 8:25 am

    #4 is such great advice!

  • […] Plus, it meets all 5 of my shopping rules! […]

  • philippamacey 06/02/2015 at 5:46 am

    Reblogged this on thevalueofbeing and commented:
    Fantastic blog post! Exactly the information every woman needs to know, especially when we are dealing with a small budget and a big love for fashion!

  • philippamacey 06/02/2015 at 5:45 am

    I’ve only just worked this one out. Perfect blog!

  • Fancy Nancy 05/31/2015 at 10:28 am

    Reblogged this on fancythat1989 and commented:
    I absolutely loved this post from A Pretty Penny. It was just the push I needed to clean my closet that I have been saying I would do since last September lol

  • This and That | A Pretty Penny 05/26/2015 at 1:25 pm

    […] On a recent trip to TJ Maxx, a pair of palm print cropped chinos got me all introspective about my ‘style journey’ over the last several years. 2012 Keira would’ve bought them without hesitation — they were cute and inexpensive, and all the other bloggers are wearing palm prints for spring/summer — but 30 year old ‘practical’ Keira reasoned that I’d likely only wear them once and the $25 was better off in my wallet. I’m totally growing up, you guys! ;) (See also: My Grown-Lady Shopping Rules.) […]

  • […] Recommended Articles: #OOTD: The Softest Sweater, Taking Stock, My Grown-Lady Shopping Rules […]

  • Emily 11/03/2014 at 6:12 pm

    Good advice! Whenever I see an expensive wardrobe piece, I always try to calculate the cost-per-wear. It’s the best way to know if you’re investing in something worthwhile, something you’ll get real use out of.

  • Baby T Fashion Diaries 09/18/2014 at 7:25 pm

    I completely agree!! I dont know how many people that seem to have a shopping addiction. But this article completely explains that. You buy a tonne of cheap random items, and then your never satisfied so you keep buying.

    I wrote an article about four rules to buy value instead:


    So loved reading this!! :)

  • Cie & Liz | Bonne Vivante 09/18/2014 at 11:37 am

    Love this whole outfit!

  • hannahlouise1406 09/16/2014 at 3:37 pm

    I need to get a hold on that ‘cost per wear’ idea lol

  • therealjlow 09/16/2014 at 5:33 am

    I am so guilty of the bad shopping habits! haha Love the list though! I think thats something that I need to stick to also! Jess

  • racheleatslegs 09/15/2014 at 5:13 pm

    Such good rules! I too am learning to live by these as I get older. Especially since I’m on a tight budget, I need to add pieces in more consciously.

    • keiralennox 09/16/2014 at 11:47 am

      I’m on a tight budget, too, so I totally get it!

  • AnnalissaMarie 09/15/2014 at 4:23 pm

    Reblogged this on annalissamarie and commented:
    This is such a smart idea !

  • dmshields12 09/14/2014 at 5:47 pm

    Reblogged this on thedirtydeedotcom and commented:
    This is the exact transition I need to be making right now. I need to start buying higher quality, more expensive items instead of cheap, fad clothing!

  • missaLAnnis 09/14/2014 at 5:34 pm

    Fantastic and true advice! Staple quality basics are a for sure smart and satisfying way to shop. Such a true comparison to food shopping or eating better I love that.

    Just started following you and really like set up of your blog..clean, pretty, and organized! What theme are you using if you don’t mind me asking? Looking forward to your posts :) xx Alanna – missaLAnnis.com

    • keiralennox 09/15/2014 at 9:14 am

      Thanks, Alanna!

      I use the Twenty Fourteen theme, with the custom design upgrade so I can play with the CSS. I think of all the WordPress themes I’ve used over the years, this one is my favorite. It’s clean and easy to customize (with or without the upgrade) and gives you lots of places for additional content (sidebars/footer/featured posts).

  • abbyhandt 09/14/2014 at 4:08 pm

    LOVE THIS! Always need to keep this in mind when shopping. Thanks for sharing :-)

  • eatdrinkbmary 09/14/2014 at 3:59 pm

    Great advice, definitely got me thinking, thanks for sharing!

  • […] learning to shop like a grown up (oh dear, I’m 41!). Keira from A Pretty Penny has her own My Grown-up Lady Shopping Rules if you are still learning, […]

  • Laura 09/13/2014 at 6:25 am

    This is great, thanks for sharing. I really love your writing style! Xx

  • Leona Tesar 09/12/2014 at 9:05 pm

    Reblogged this on THE NEW BLACK and commented:
    First, what an appro title for this post. Second, very smart advice for style-snipers of every age and stage! Clever!

  • Parisa Tasbihi 09/12/2014 at 9:57 am



  • beff2002 09/11/2014 at 9:01 pm

    Ha.. I love “does it fit”… As I have recently retired my 20s and now entered my 30s… I have definitely found it true that it is now time to purge my “look how trendy I am 20’s clothes” and dress a little more fitting for this phase of my life!! Easier said than done though!!

    • keiralennox 09/12/2014 at 5:15 pm

      It is easier said than done! I’m making myself feel better about the transition by buying myself some special timeless pieces (still on sale, of course).

  • amybareham 09/11/2014 at 7:25 pm

    Thank you for this post!!! I love the CPW concept and I think you’re exactly right – saving up to get quality staples makes so much sense. Clothes are their own investment of sorts. I guess we just get carried away when we see the word “clearance.” Anyway, thanks again for a thoughtful post on being fashion savvy.

  • sanneyckor 09/11/2014 at 6:46 pm

    Great *_*

  • dejavuufsa 09/11/2014 at 6:15 pm

    cool but tooo much show off. sorryyy

  • evervescence 09/11/2014 at 12:39 pm

    This is great advice! Thank you so much. :) That outfit also, the yellow and grey with those cute shoes, is incredible. I’m a 5’5″ hourglass (very busty uptop) so I relate. I’m in the midst of a big purge and feeling extremely anxious about how to buy new things and create a wardrobe that fits, is stylish and most of all reflects me and my personality. I already feel I have nothing to wear though so I guess it won’t be too hard, I just don’t want to make the same mistakes again and fill my closet with cheap clothes that don’t fit well and that I don’t love wearing. Thanks again for the great advice.

  • varellano 09/11/2014 at 11:14 am

    CPW is my primary justification for shoe purchases. I am too old to buy ill-fitting, cheap shoes. My feet cannot handle it and in the end they do more harm than good. I’m with you on the quality-hunt!

    • keiralennox 09/11/2014 at 12:24 pm

      SO. TRUE.

      I’m on my feet all day at the flower shop, so shoes are super important for me now. What are your favorite shoe brands?

      • varellano 09/11/2014 at 12:38 pm

        Indigo by Clarks, Born (especially Born Crown), Sam Edelman, Sanita (they have some adorbs clogs), Kork-ease, and TOMS for the weekend!

        Gentle Souls shoes are amazing, but still way out of my price range. I’m keeping an eye out for flash sales, though!

  • RoseGoldPout 09/11/2014 at 10:37 am

    Ahh! :D These are great. Once you read them written down, you realise how often you’ve talked yourself out of following important rules like these. Might have to print these out and pin them up! :)

    • keiralennox 09/11/2014 at 12:23 pm

      Accountability has been *everything* for me this year in getting my shopping under control.

  • stefik12 09/11/2014 at 8:49 am

    Please read my fashion blog… http://fashtenn.wordpress.com/

  • Amy Fashion Blog 09/11/2014 at 8:08 am

    So going to have to use your tips

  • lafaiseusedebetises 09/11/2014 at 6:30 am

    J’aime beaucoup c’est trés joli! :-)

  • vestitini 09/11/2014 at 6:17 am

    I like it

  • graciebeautyfashionlifestyle 09/11/2014 at 5:53 am

    Hi! I nominated you for the Sisterhood of the World Bloggers award because I love your blog! Just look at my last post for the details. :) :D Also, very informative blog post!

  • rambleonrockstar 09/11/2014 at 2:55 am

    As a fellow short hour glass, learning to dress for my body type has been the most important lesson for me. Everyone always says they can tell if something is ‘my style’ immediately, but hey if it works right?

    • keiralennox 09/11/2014 at 12:22 pm

      It’s tricky, right?! The majority of things are way too long; if it fits my butt it doesn’t fit my waist; etc. What are your favorite styles?

      • rambleonrockstar 09/12/2014 at 5:48 am

        It really is! My favorite thing to wear is a cinched waist dress with a fuller skirt. It’s super feminine and it’s one of the styles that I know will look nice no matter what. I have to be mindful when wearing anything super flowy (it looks less dainty and more maternity on me), and I usually pair them with super slim bottoms. If I’m not highlighting my waist, I’m showing off my shoulders or my legs. For me it’s finding a balance and highlighting my shape without going overboard!

  • beautyinthebeast2 09/11/2014 at 1:57 am

    Reblogged this on and commented:
    I absolutely love this! I was once a shopaholic that bought stuff that I would end up never wearing but about 6 years ago when 8
    I became a mother I had to think budget and quality and I’m quite impress with what’s in my closet. Good read! 👛💳💻😍😍😍😍😍😍

  • lacypreston 09/10/2014 at 10:43 pm

    Love this color combo! :)

    xoxo Lacy

  • scatteringcheer 09/10/2014 at 10:08 pm

    I love these rules, and completely agree with them! Now, if only I could discipline myself to follow them :)

  • Erin's Notions 09/10/2014 at 8:31 pm

    This post is so spot on. I have always been obsessed with a vintage look and have been drawn to more classic pieces. Though I looked more mature than my counterparts when I was in college, I still have pieces in my wardrobe from over 10 years ago. You don’t even have to spend a lot on clothes, just spend it wisely. I try to follow the rule of it you love it, you buy it. If you love something it will be with you for a while :)

    • keiralennox 09/11/2014 at 12:20 pm

      “You don’t even have to spend a lot on clothes, just spend it wisely.” Nailed it.

      I love your style!

  • luxmannequin 09/10/2014 at 7:25 pm

    Awesome article! Now that my 28th birthday is around the corner in October, I feel the need to shift to owning higher quality clothing items versus getting cheaper stuff that looks sexy.

    • keiralennox 09/11/2014 at 12:19 pm

      28 was such a great year for me; I hope it is for you, too! Good luck on your style journey. It’s been really interesting to see the way my style has changed over the last several years.

  • frillthrills 09/10/2014 at 6:39 pm

    Oh my god I love this post. Every tip is so valid and as of now I follow only rule 1. Lol.

  • wondersreviews 09/10/2014 at 2:30 pm

    Great post Keira ! I’m also more careful now when it comes to buy clothes.
    I dont buy lit of clothes now.
    I ask myself : is it timeless or a quick trend ? Would i still wanna wear it in 3 years ? When you hesitate, check the détails, they can tell you if it worth the splurge or not. If you dont hesitate, it means that it’s too lovely to leave it. Most of time my fall in love pièces are cocktail dresses. I collect them like treasors. XD
    WondersReviews Recently Posted : [Dior]Addict Extreme;Rouge Dior Baume Lip Treatment; BackstageBlender[Review,Photos,Swatches]

    • keiralennox 09/11/2014 at 12:18 pm

      I wish I collected cocktail dresses; I need one for an event tonight and I’m sweating it.

      I love what you said about hesitating. There are some pieces that I just know I want immediately (love at first sight and all that :)). If I’m on the fence, I walk away to think about it. This has really helped me with impulse-buying; 80% of the time I don’t go back for the things I hesitated over.

  • sashilove21 09/10/2014 at 2:29 pm

    I am beginning to realize quality is better than quantity when it comes to my wardrobe.

  • sirwin17 09/10/2014 at 2:00 pm

    I agree with you 100%, except if an item is too big it can usually be tailored. Besides, most items can’t fit everyone’s body perfectly. When my sister did modelling, everything was tailored to her body and even the cheapest items looked expensive because of it. Love this post though <3


    • keiralennox 09/11/2014 at 12:15 pm

      You’re so right about tailoring. I wish I had the extra money to spend getting everything custom-fitted to my body; it makes an exceptional difference. There are a few pieces that I’ve splurged on to make them fit just right, and it’s so worth it.

  • lindsaybb 09/10/2014 at 1:57 pm

    Yes to paying attention to fabrics! As I’ve gotten older, I care ~so much more~ about this.

  • tinybeautyblogger 09/10/2014 at 1:47 pm

    I am nearing 30 and I still haven’t figured it out. I can dress fun/funky/trendy, but when it comes to looking sophisticated, I just miss the mark completely. I work in an office, and have no idea how to shop to officewear. It’s frustrating because now I am at the age where I can walk in and out of a Forever 21, and not buy a thing because it no longer fits the looks I want to go for, or isn’t appropriate for the body I’ve grown into.

    • keiralennox 09/11/2014 at 12:14 pm

      This is why I love style blogs so much. Try finding some blogs that focus on office style, like http://www.theclassycubicle.com. She does outfits that are work-appropriate but still young and fun.

      Lately I’m really loving Loft; their pieces are affordable and fit well, and hold up for a long time. They have a great selection of work basics, like pencil skirts, trousers, and dresses that you can put your own spin on with shoes and accessories.

  • Alexandra Steinmetz 09/10/2014 at 1:44 pm

    This is awesome advice! I started doing this about a year ago. One of my other, personal needs in my wardrobe is that I try to buy high quality pieces that are ideally sustainably made. I limit my made in China fashions and buy brands like Steven Alan or Nanette Lepore (but let’s be real, all via eBay and used). It definitely means buying less but I’m much happier with my purchases!

    • keiralennox 09/11/2014 at 11:59 am

      Yes, this!! I’m really trying to be more conscious of sustainable fashion as well. Thank you for the recommendation on the brands! I’ll have to knock the dust off my ebay account and check these out. :)

  • navigatinglandscapes 09/10/2014 at 1:39 pm

    Excellent advice, Keira. I started these similar rules when I was about your age (I am now 46). Happily, I now have a fabulous closet full of timeless pieces, some of which I have been wearing for almost 20 years! Quality over quantity means a girl alwasy looks her best! :)

    • keiralennox 09/11/2014 at 11:57 am

      This is my goal!! I really hope that, going forward, the majority of things I purchase will be things I’ll love for a really long time. Thank you for the feedback!

  • Mel 09/10/2014 at 1:33 pm
  • Beth Dahleen 09/10/2014 at 1:24 pm

    I like “Is it on the List”? Kind of like a grocery shopping list while clothing shopping. I am still working on my list of must haves for my closet.

    • keiralennox 09/11/2014 at 11:55 am

      Exactly! It really helps me stay on track and avoid impulse-buying a bunch of stuff I think is cute.

  • Lisa Bates 09/10/2014 at 1:12 pm

    It’s awl about the PPdub! 😜

  • whennothinggoeswrite 09/10/2014 at 1:09 pm

    Haha will it play well with others. Good call. I’m definitely the bad shopper that buys quantity over quality.

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    keiralennox.com and related social media accounts contain advertising and affiliate marketing links from ShopStyle; I earn a small commission from clicks and/or purchases of linked items. keiralennox.com is also a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to amazon.com.

    Any gifts or services that brands/companies send to be featured on this blog are clearly disclosed as “Courtesy Of” or “c/o” in each applicable post. All views and opinions are my own, and if I wouldn’t use/purchase a product or service myself, I won’t feature it on the blog. Because friends tell each other the truth. Cool?