My Clothes Shopping Rules

Goodwill finds: LOFT jeans, LOFT sweater, toddler (look for yours in the stuffed animal bin)

Last Saturday I told my husband that I just wanted to peek inside Goodwill for a pink sweater, and then we’d be done, I promise.

An hour and a shopping cart full later…..

I really don’t spend much on myself, besides medical bills, coffee dates, and the occasional cute outfit. Spending money paralyzes me. Shopping overwhelms me. Decisions in general make my head spin, so it’s not exactly my idea of a fun weekend to hang out at the mall.

But Goodwill’s low prices mitigate some of that fear. So much, in fact, that I’ve got a bag of rejects sitting in my closet waiting to go back to Goodwill.

That’s one of the weird things about being me. I freak out about spending money, and then when I do, I inevitably buy something I don’t even like that much.

Since I clearly have issues knowing my own mind and then making it up, I’ve had to develop some clothes shopping rules. They help me make a decision when I need to make one, and they keep me away from embarrassing impulse buys. (The cheetah print skirt….)

The Rules

(1) It absolutely must fit. Perfectly. If it needs hemming or taking in, forget it. It’s an automatic hard pass if I find myself thinking, “Well, it’ll fit if….” I don’t like belts, I can’t sew, it won’t happen. This rule prevents 90% of all purchases because I am too short for most bottoms, too embarrassed to wear most shorts, and too skinny to fit into almost everything else.

(2) It needs to coordinate with with multiple items in my preexisting wardrobe. Last year, I decided on a color palette (olive, pink, denim, gray, tan, chestnut, bright white), a color saturation (muted, some pastel), and a style (looser shirts, skinny jeans/leggings, long sweaters, some slight, tentative ventures into boho/hipster/vintage worlds). I can pretty much pick any random pair of pants and any random shirt and throw it together with any sweater. Voila, an outfit! Several things don’t exactly go with the New Me (and to be honest, I don’t exactly wear them, either). While I can’t work up the courage to get rid of these un-matchy pieces, I sure try my darndest not to bring any more of them home from Goodwill. If I can’t match the article of clothing to at least a couple of my regular outfits, it’s going back on the rack with a wistful farewell.

(3) I need to be able to wear it at work or church. Gone are the college days where cold shoulders or super high heels could even remotely be appropriate. Gone too are the days when dressing preppy for class or, at the other extreme, lounging in sweatpants, was a daily probability. I get ONE singular Saturday a week to wear something not work-appropriate or church-appropriate. Since I’ve already got lots of competition for that spot (short shorts! ripped jeans! graphic tees!), I don’t buy anything I couldn’t wear to work or church. I know now that I just won’t wear it, no matter how cute it looks in isolation from my real life. In case you’re wondering, I can wear normal clothes to work — even athleisure.

(4) It needs to fit with and cover the bra types I already own. You feel me? None of these weird straps and cutouts and necklines that are made for braless prepubescents and recklessly marketed to adult women.

(5) It needs to be well-made but easy to care for. This is actually a new rule for me, developed after reading Overdressed: The Shockingly High Cost of Cheap Fashion, by Elizabeth L. Cline. It should feel substantial, not thin or see through; be tailored well; include nice details; wash without turning into a permanently rumpled mess; and have no stains or holes. (Because, again, it’s delusional to think I’ll get around to fixing it.) I now try to avoid fast fashion brands that use cheap materials (even though my entire wardrobe is hypocritically Old Navy).

Last but not least: (6) It needs to be something I’ve wanted for awhile. I’ve got a running wish list: I’m on the hunt for a pleasantly colored yellow something in my life, a pink cardigan (maybe floral, please?), a white calf-length tulle skirt, a shirt with dinosaurs or hedgehogs or sloths or llamas (channeling my inner Ms. Frizzle here), those cute high-waisted shorts that tie in a bow, and maybe — the unicorn of petite clothing — a maxi skirt that doesn’t trip me onto my face. These are things I persistently find myself drooling over whenever I encounter fashion. They stay with me over the years and the Google searches. They are my true loves and my real style. And when I find them at Goodwill for $7.99 like a fated meeting — I feel absolutely no hesitation buying them.

Just last month I stumbled upon a leather jacket in exactly the color and style I’ve wanted since forever. It makes me happy in a way a leather jacket probably shouldn’t make me. I’m so glad I didn’t settle for the Target one that didn’t fit quite right, or the online one that cost a fortune. True love waits.

This rule also helps me make rational decisions when the price tag is high. If I’ve been wanting a piece for forever, I feel more confident spending a bit extra or buying it brand new instead of off the Goodwill rack. I know it’s not an impulse buy, so I’m okay forking over money for good quality and the exact look I want.

While I’ve got a lifetime of impulsive and disappointing buys to educate me, these rules really flow from that satisfaction of finding just the perfect piece for a price I’m willing to pay — and then loving it every time I pull it out of my closet.

Do you have any clothes shopping rules?

12 thoughts on “My Clothes Shopping Rules

  1. bethanydurie

    I NEED to take you to Autumn’s Closet! It’s like Goodwill, but with only cute clothes. Let’s make a date and go buy bad clothes together. :P

    I’m still in a process of figuring out what my vibe is. I like boho, but I don’t really pull it off. And I wear my Y T-shirt most days. So ew. Haha and when did you EVER wear high heels and sleeveless shirts? I want to meet this college Bailey. ^_^

    My new problem now is thrifting for kids clothes. SO CUTE. SO CHEAP. Eeck! (Probably not a problem with you, yet. Boy clothes thrifting is incredibly meager and sad….)


    • Bailey Steger

      Let’s go!!!!

      I think you could totally pull off the boho vibe! Especially since you know how to get nice wavy curls and style things.

      Thank you for validating my dislike of thrifting for boys’ clothes. 😂 It’s a sad venture, indeed.


  2. Lyndall Cave

    This article has THE BEST use of “true love waits” I’ve seen. 😂

    Thinking about my clothes shopping rules, I have mostly the same as you. It has to fit well, coordinate with the other stuff in my wardrobe, be able to be worn multiple ways, and be well-made without stains, tears or snags. I rarely buy new clothes, mostly always from thrift stores, hence the last rule.

    I have one more rule that’s different: If it’s touching my skin it has to be mostly natural fibres (cotton, linen, silk, bamboo, rayon – probably not wool). I hate the feeling of polyester, nylon and acrylic touching my skin, and they don’t breathe well. Man-made fibers get relegated to sweaters, if anything.


    • Bailey Steger

      I was really proud of the true love waits line. 😁

      Oo! I haven’t paid attention to how different fabrics feel. I do know that the one silk dress I own is the most magical sensory experience ever, so maybe I should pay attention to the clothes tags more often!


  3. Mari

    I LIVE by rules 1, 4, and 5. So good.

    I have been actively trying to buy items that are a fun color/pattern that doesn’t match the rest of my wardrobe… a bright orange sundress, some colorful jeans… to break up what is otherwise a pretty monotonous closet of grey, blue, and dark purple. I have a tendency to get stuck in a fashion rut and only buy items that look like stuff I already have. Not only is this boring, but it’s sort of wasteful since that makes many pieces in my closet superfluous.


  4. A

    A lot of your rules sound very similar to mine! Here are my clothing criteria:

    –Quality matters. It shouldn’t be so cheaply constructed that it pills, unravels, or fades after just a few washes, and it absolutely cannot be made out of that sad, thin jersey fabric that displays every underwear outline to the world. (I’m looking at you, Old Navy!)

    –Natural or mostly natural fibers are a must. Polyester isn’t biodegradable, and it always makes me feel hot and sweaty (and it shows pit stains more easily, too).

    –It can’t be a style, print, or silhouette that will look dated in just a few years, because I hope it stays in my closet for *at least* that long.

    –It shouldn’t require specialized cleaning unless it’s a piece of formalwear that I’ll only need to clean once a year or so. Generally, I cold-wash and line-dry most of my wardrobe, but I avoid buying pieces that might bleed, stretch, or shrink if I were to accidentally stick them in a hot wash cycle or run them through the dryer.

    –It has to fit me perfectly or almost-perfectly (I can do very basic alterations and hemming, but that’s it). I don’t want to wear anything that requires constant adjustment because the hem is riding up, the wrap front is coming untied, or the neck is gapping.

    –It has to go well with at least a couple of pieces in my existing wardrobe. I don’t like buying anything that requires a new coordinating cardigan, skirt, belt, etc. (If it’s a skirt or dress, it absolutely has to match one of my jackets or cardigans, because I’m a perpetually cold person who brings extra layers wherever I go!) And if I have to buy a new bra because it has a weird neckline–forget it!

    –Skirts, dresses, jackets, and pairs of pants really should have POCKETS. Ideally, super deep pockets that I can awkwardly stick my hands into when I don’t know what else to do with them, lol. (I’m such a fan of pockets that I’m considering learning how to add pockets to skirts and dresses that don’t have them. How hard could it be??)

    –If a particular item really works for me and fits all the above criteria, I don’t mind spending a decent amount of money on it. In fact, I may buy it in several different colors/styles.

    You mentioned that your style has changed a lot since you left school; I’m curious how being a mom has factored into that. Are there any ways your wardrobe has changed since you had your son? I’m hoping to start a family in a couple of years, and I’m starting to think about how certain pieces in my closet could be incorporated into a maternity/postpartum/nursing wardrobe, wondering if I really will have to throw out most of my pre-baby jeans because they won’t fit me anymore, etc…. I have no idea how drastically pregnancy/motherhood will affect my body and lifestyle, so I’m curious to hear your experience, if you feel like sharing it. :)


    • Bailey Steger

      POCKETS. How could I forget to include a rule dedicated to real, functional pockets?!

      The only thing that changed about my wardrobe post-partum is that I can’t wear dresses publicly if I plan on nursing. I never bought any nursing bras or clothes — lies: I bought ONE nursing bra but never could snap it back together in a timely, unawkward way, so I ditched it. :P I fit back into all of my pants about a month post-partum, but I didn’t have a lot of extra weight during pregnancy, and breastfeeding burned a ton of calories quickly for me. I way about 10 lbs. less than before pregnancy, so I actually had to buy new pants in a smaller size. Pretty sure I’m in the minority there. The one weird thing about pregnancy/post-partum/nursing/post-nursing is that breast shape and size fluctuate so much, and it can be hard at times to fit into old bras!

      When pregnant, I wore leggings and overlarge shirts almost exclusively, and carried that into my breastfeeding days — it made everything easier, plus the early days of breastfeeding involved so much spills and spit up and poop stains that I rarely bothered with anything fancy. But now that I breastfeed less, I actually dress up for everyday a lot more than my non-mom friends. I was deprived of cute clothes for so long as a pregnant/spit-up-covered woman that I truly enjoy the freedom to wear dresses and heels. That’s another thing: I couldn’t wear anything but supportive flat shoes while pregnant, and even then my feet suffered. Oh, and make sure you get coats and sweaters that fit over a pregnant belly!


      • A

        Thanks for sharing! It’s nice to hear an experience other than “I had to throw out my entire pre-baby wardrobe,” haha. (Of course, I’ll do that if I have to, but…it’s helpful to hear that it isn’t necessarily inevitable.)

        Ugh, I didn’t even think about coats and sweaters. Maternity tops and pants are one thing, but dedicated maternity outerwear seems a bit more daunting to buy! And new bras. Gah. Bra shopping is a whole other level of annoying!


  5. Christine

    I first came to your blog for egalitarian reasons. I’m happy to find your are also a bit of a Bargain Barbie like me! I grew up poor and that genetic frugality follows me into my 30s. We don’t need to feel shame for shopping second hand anymore, in fact it seems to be trending! I found an entire Ann Taylor outfit from the Salvation Army a couple months back. An outfit that off the rack would have cost at least $70-100, I was able to get for less than $30! Being poor taught me to be patient, and even now I do have to admit, I enjoy the hunt. It’s wonderfully rewarding to still be able to do something like treat myself to a cute outfit that does not break the bank. ^_^


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