You Need Help: How Can I Expedite My Style Evolution?

Q: Gaby Dunn looked perfectly good at 20, but it seems like she’s recently really settled into a style that fits her well and makes her happy. How can someone like my 21-year-old self find their style fit sooner rather than later?

Images via Gaby Dunn

A: This is such an interesting question! I love discussing fashion as an important mode of self-expression, but I’m also aware of how the financial and size inaccessibility of clothing and makeup, the implicit and explicit body shaming that works to keep us conforming, and an understanding of the myriad objectionable facets of capitalism can impede a person on their path toward a “signature” style — assuming signature style is a real thing for everybody, and that style isn’t a naturally evolving journey for at least some of us. Whatever the case is for you, here a few ideas to help you along your way:

Diversify your Instagram/Pinterest/Tumblr/etc.

Image via Instagram

Social media has its pros and cons, but one thing I really love about it is exactly how accessible it is for people across the economic, size, shape, color, gender, and dis/ability spectrums. Gone are the days in which Vogue got the final say; in the last decade or so, platforms like Instagram and Tumblr have played an enormous part in democratizing fashion. You know, like blogs have always done, except you can find way more resources via a single hashtag (like I did above with #lesbianfashion)! What!

Whether or not you’re “a social media person,” I encourage you to use tags and other search features to find people whose aesthetics resonate with you, and whose bodies actually look like yours — then follow them for free daily fashion inspiration that’s way cooler than anything legacy media has to offer. (Unless of course I get hired to write something for a legacy media outlet, in which case, oh dear god please support my work.)

Try On a New Look Using Virtual Makeover Apps

Image via ModiFace

Selfie-driven apps like Hair Color Booth, Hairstyle Magic Mirror, and Hair Changer Mens Hairstyles (I know, I know, but how else are you supposed to get that perfect pompadour?) will let you virtually try on new ‘dos, while Makeup Genius and YouCam Makeup offer zero-commitment simulations for the cosmetic-curious. There are several makeover apps available via both Apple and Android, so look around and find what works best for you — or if you’d prefer to keep things on desktop, try your hand at ModiFace‘s web makeover tools.

Hold a Clothing Swap

Image by Beatrice Murch via Flickr

Saying this makes me feel like such a Gwyneth Paltrow. “Hold a clothing swap!” she unblinkingly exclaimed, as if everyone has the similarly sized friends or even space necessary for holding one. But if you can, do! You may even be able to organize a swap at a nearby school or religious institution that will help folks outside your friend group, too.

Thrift, Trade, or Consign

Image by Brad.K via Flickr

If I love the print of a textile enough, I’m not worried about its condition. I’m pleased as punch to walk around like Park Slope’s own Dickensian orphan, some of which is owed to my flea market-filled upbringing and some to my immense privileges of being white, relatively thin, cis, and able-bodied, and working for myself in a city known for its creative types. Which is all to say, I get it if the idea of thrifting gives you pause. You may find, though, that chains like Goodwill, Unique, and Value Village often stock rarely (if ever) worn items at a fraction of their original price, as well as offering customer rewards programs and discount days. And if you live near a consignment store or Buffalo Exchange-type situation, you may even be able trade in your old clothing for credit to pick up new (to you) stuff. Hooray!

In addition to the incredible value secondhand stores provide, they’ve also facilitated my style evolution by putting things in front of me that I otherwise might never have tried (which clothing swaps could definitely do too, TBH). If you have a free Saturday afternoon, it may be worth it just to stop into your local ValVil and experiment!

Take Advantage of Secondhand Sites and Apps

Image via thredUP

Of course, you may not live near any of those places or be able to get to them — and, as with firsthand shopping, it’s true that certain sizes are significantly tougher to find at secondhand stores than others. That’s where sites and apps like thredUP, Depop, Mercari, Etsy, Poshmark, The Real Real, Vestiaire Collective, and ResellXL (specifically for plus-sizes), which you can search by size or keyword regardless of your location (at least, within the US) come in. Certain sites and apps will be a better fit for you depending on your budget, measurements, and desires.

As Well as Auction Sites

EBay is still the biggest name in online auctions, but some IRL secondhand stores run their own as well! Goodwill offers items starting at true thrift prices, while Housing Works lists mostly designer or otherwise exceptional pieces. It’s not the absolute cheapest, but it is where after years of searching, I finally found the fancy handbag of my dreams at a price I could actually afford. And, at least for me and my amount of expendable income, parting with three digits’ worth of money hurts less when it’s going to an organization doing such crucial work for my people.

Whatever secondhand or auction platform you choose, scour each seller’s return policy and reviews; don’t hesitate to ask questions on exact measurements, etc., since number sizes vary so widely; and, in the event of an in-person transaction, always make sure you’re keeping yourself as safe as possible.

Try Some Low-Commitment Changes with a Subscription Service


If secondhand shopping isn’t for you, you can still explore your style via subscription services like StitchFix and Trunk Club, Gwynnie Bee and Dia & Co (both plus-specific), and Greyscale Goods and SprezzaBox (dapper/andro fashion FTW!), as well as makeup and grooming services like Ipsy and Birchbox Men. Different services have different pricing options and contracts, but as with my thrift epiphanies, they all have the potential to surprise you with a style or product you’d never try otherwise.

And Use Honey to Save Even More

Image via Missguided

I know that header feels weird and sponsored, but I promise it isn’t — I’m just Honey‘s biggest fan, and I don’t want to keep my love a secret any longer. Honey is a browser plugin that will automatically find and run coupon codes for you at various stores, so you can buy on sale on top of sale on top of sale. Obviously use responsibly and maybe not with indie makers who could really use every dollar, but $30 saved at Walmart could buy you a yearlong A+ membership instead. Pretty sweet, if you ask me!

So, those are my tips for making style more accessible to all! Leave yours in the comments — and if you have a fashion or beauty question you’d like answered, send it to nora [at] autostraddle [dot] com.

Nora is a writer and shoot producer living in Brooklyn. Send her links to weird clothing and dog videos to nora [at] autostraddle [dot] com.

Nora has written 53 articles for us.

32 Comments

  1. I found that I really came into myself when I was travelling by myself. There were no preconceived notions about who I was or how I presented. Every moment felt very authentic.

    I’m not saying you have to go travelling, because that was a momentary luxury I could afford at one point in my life that not everybody has (and I don’t now) but I think there is a way to recreate that feeling. You could try dressing as if you were going out with friends when you’re just going to muck around on your laptop by yourself, dress as if you’re going for dinner when you’re just making yourself a pot of Kraft Dinner. And just dress how you want to dress in those moments for yourself.

    And acknowledge what you find limiting or missing in your wardrobe. Notice what pieces of clothing don’t apply to you anymore or make you feel like your best self and donate them or do a clothes swap with friends.

    It’s an exhausting and empowering process. Good luck!

    • Yes!! Dressing up for hanging round the house really helped my mental health on days off. Also i could try stuff i loved but didnt feel confident about. Then, id pop to the shop, or my housemate would bring a friend round and before you know it that outfit was one of my regulars. Dressing for my living room bridged that gap between trying something on and wearing it in front of people.

  2. I didn’t hit my style stride until my late 20s- downside is most of my old photos make me do a full-body cringe, but upside is I manage to pass by people I’d rather not make small talk with, as they don’t recognise me in time.

    The more I started doing things for myself (in terms of what made me happy, the way I do business, etc.), the more clear my ‘signature’ style became. I was a lot less hesitant to incorporate things I’d never try to pull off in the past- even if it was a big leap, I adhered (and still do!) to ‘fake it til you make it’.

  3. “then follow them for free daily fashion inspiration that’s way cooler than anything legacy media has to offer. (Unless of course I get hired to write something for a legacy media outlet, in which case, oh dear god please support my work.)” omg dying.

  4. I think style comes with confidence and a willingness to try things that might feel goofy at first. I hit my style stride around 28-29, which is also when I felt the most confident in who I wanted to be as a person. Also like, just wear things that make you feel good and eventually you’ll find what you like!

  5. These are also handy money-saving tips for people like me who feel comfortable in just about any style and don’t have a “signature” look. Many thanks for showing me the wonder of ResellXL because I have some old clothes from Torrid I might try to part with.

    A note on subscription cosmetic boxes, Ipsy is NOT vegan friendly and cannot guarantee that you will only receive vegan/cruelty free items. So, if you’re a vegan, or just try to shop cruelty-free like me, you might want to try other services (crueltyfreegoddess on Instagram posts and occasionally reviews cruelty-free/vegan sub boxes that contain makeup, but off the top of my head VeganCuts offers a beauty box).

  6. Re: clothing swap

    Boston has the most AMAZING and affirming clothing swap once a year in May called the Big Thrifty. All plus size fashion, a few local vendors, and everything is so cheap! I bought 5 dresses, a jacket, and a top for $65. It is super inclusive of all genders, sizes, and abilities. And the stuff is great! I almost bought a wedding dress for $10 but was worried my boo would get the wrong impression lol.

  7. These are really great suggestions! I discovered fat fashion instagram in my mid-20s and it changed everything for me. It improved my self confidence and healed some of the lasting emotional scars that 20+ years of consuming “legacy media” lad left on me. It also helped me open up to such awesome possibilities of what I could wear. Single handedly instagram and tumblr changed my femme expression in all the best ways.

  8. Clothing swaps are my new jam! A small group of us started one here in my town about 18 months ago, and started inviting new people each time until our list is now over 100 people. There’s a huge variety of sizes of people, and anything we don’t want ourselves gets donated to local non-profits (usually women’s shelters).

  9. These are great! I only feel like I hit upon a style that works for me when I was about 28, but started searching for one at about 25 (I’m 31 now, so not that long ago). First it took spending some time on Pinterest to figure out what I actually liked, boiling it down to a set of principles to follow (that I can always break because it’s just my own style) and being fairly ruthless about what I bought, both for $ reasons and because I was tired of having clothes in my closet that I wasn’t completely in love with. I also had to tackle my internalized misogyny and devaluation of femininity and come out as femme. Moving cities (for unrelated reasons!) helped, because I could try on a new style and not feel as though people expected me to look the way I always had, since no one knew me!

    Now I am working on really owning my femme-ness and taking strength from it. Style is so important to me because it give me some control over the way I look and present, which gives me the confidence (mostly) to stand strong in my identity.

  10. another huge thing is finding a good tailor – the concept seems fancy but it’s actually significantly more affordable than most retail stores AND you will be able to create a look that fits your body and feels good

    I personally have two tailors I like – one who is more expensive that I use for suits and more complicated alterations and one who I use for small things like hemming oversized shirts to crop where I want them

    you can buy a shirt or pants at a thrift shop for < $5 and have it fitted to you for often < $20 (if not <$10) and the best part is through pinning and discussing you can truly craft your look through experimentation IRL

    just like going to the hair salon, be super clear with them because as we all know once something is cut off there's no going back

    and bonus: tailors will fix that uncomfortable feeling of button-downs either being too tight across or way too big and unflattering!

  11. How might I go about undoing/redoing my style? In a period of mourning/intense depression, I made myself a capsule wardrobe and like a lot of it- it’s easy to pick an outfit that matches, stuff fits well, and dressing goes much quicker (which was good for my low energy depression brain!). But I’m feeling a lot better now and missing when my clothes weren’t all black, blue, purple or gray and fashion was more fun and experimental. If I want to be excited by my clothes again but not lose the benefits of having a cultivated style, what do I do?

    • I’ve done something similar when I had depressive episodes. It can be overwhelming to try to jump back into fashion after having a “uniform” of sorts for so long.

      I started with accessories and shoes as ways to “dress up” my outfits and add variety without going too far off what I was used to. Black pants and a t-shirt look WAY different with a faux-leather choker/wrist cuffs and Docs than it does with a simple silver chain necklace and heels.

      Then I started buying things one at a time–statement pieces that still paired well with what I had in my closet (usually I’d buy a blouse-y type thing I could wear with my pants). Also leggings. Leggings are great, because I could wear roughly the same outfit every day (leggings, shorts, t-shirt) but it LOOKED different because you can buy leggings in all sorts of patterns/styles (usually for pretty cheap, too).

      Makeup is also pretty good for having experimental fun with your look without having to change your wardrobe around too much, if you’re into that sort of thing. It can be a hassle to spend forty-five minutes putting on your face (especially if you’ve gotten used to using that morning prep time for other things, like making more coffee). BB creams or mineral foundations are good for quickly getting a base face done, and colorful eyeliners or mascaras can add color to your eyes without having to spend a lot of time putting on eye shadow. I also own about twenty different shades of liquid lipstick which take all of three minutes to put on and completely change my look depending on the color.

      Hopefully some of that can help you? Good luck and I’m glad you’re feeling better!

  12. I’m certainly no fashion expert, but I’ve found that what works for me is:

    a) When I find a look that feels like ME and makes me go “hell, yeah!” to the mirror, I make a uniform out of it. Two outfit ideas like that is basically all you need to build a consistent-looking wardrobe that makes you feel great. Just switch colours and fabrics around.

    b) I define my look in an “elevator pitch”, and then I don’t buy or sew anything that doesn’t perfectly fit that, no matter how much I like the pattern or colour. My personal elevator pitch is “metalhead grows up into highly successful creative professional”.

    c) This isn’t for everyone, but everything in my wardrobe must go with everything. Always. If it’s laundry day and I only have one top and one bottom they must go together. Also: all my accessories (shoes, gloves, handbag etc.) match. Except for that one pair of red stilettos whose very point is that they stand out from everything else. This saves me a lot of money, it saves me a lot of time thinking about what to wear, makes my wardrobe very tiny, and also makes my style consistent and identifiably “me” at all times.

  13. I have been having trouble with this for the longest! I find myself mainly drawn to androgynous fashion, but I also consider myself to be somewhat femme as well. When I was younger, I pretty much had my clothing picked out for me. Now at 25, I’m still trying to figure out my own style lol.

  14. I love how easy it is to access queer fashion on instagram and other social media. My style has definitely developed in the last year or so and it’s been a mixture of following a tonne of babes, and becoming more settled into myself now I’m in my mid-20’s

  15. Thread for not American second hand sites/apps and subscription services! Please lead with the location.

    My paltry contribution:
    Anywhere? YMMV: Local buy/sell Facebook groups! My city (Wellington, NZ)’s group gets a fair bit of second hand clothing ranging from loved to “bought this online but it didn’t fit me and we’re too far away to bother returning it”.

  16. As a non-artsy math nerd, I’ve found my zone in tomboy-femme basics, honestly. I wanted to be “cool” for so long, trying all sorts of phases; there’s comfort in aging out of that. I’m really sensitive to colors so I have to listen to my gut on palette issues. Sometimes I buy a heap of cheap stuff at Goodwill and donate a bunch of it after a month or two. Investing in staples (like my Clarks oxfords, or Etsy earrings and headbands) stresses me out because I get bored of things easily, so I do it very infrequently.

    Self-expression is so important, but it’s not everything. It’s ok not to have one style, and it’s okay for your outfit to be plain and boring sometimes. People will love you no matter what; now go forth and do you!

    • THIS. I feel like I don’t have “style” because I mostly wear basic stuff: trousers and t shirts, sweaters on top in the colder months. I’ve tried stuff I thought would look cool (like an edgier look) and just feel self-conscious in it.

      But then this super stylish, cool femme told me “no you do have a style and it suits you!”.

      You do you is what I mean.

  17. Here to be That Fucking Person That Always Makes Spreadsheets about it! Literally, spreadsheets. Keep track of what you wear, how it makes you feel, what you like/dislike about it. You’ll find that there are probably different things that you like but you maybe never realized that there was a common thread between them. Once you get in the habit of thinking about each piece and its characteristics, it starts to become a lot easier to figure out what will work together and the direction you want to take your wardrobe.

    The best thing is to take a daily picture of your outfit in the morning but literally who has time to do that.

  18. I’ve begun branching out in style a bit, almost entirely thanks to the wonderful character who goes by the name of Dr Jillian Holtzmann. Essentially, I buy stuff I like – and when I’m standing in that fitting room thinking over whether I should get it or not, I evaluate whether I’m hesitating because I would be scared to wear it irl. If that’s a yes, I buy it. And then the next day I wear it. And I think about Holtz rocking literally everything she puts on her body and I try to embody that. My budget is suffering slightly but the rest of me is great! I’m finally finding a style that’s not the most bland thing ever!

  19. Ugh I just got a bold hair color I’m really not liking and I wish I’d tried one of those apps to better communicate with my hair stylist. I was trying to trust that she would interpret the things I’ve shared in the best way for me but honestly I feel like I look stupid in a way I can’t hide now 🙁 Dreading work tomorrow.

    • <3 go back and tell her ! she'll probably change the colour. it's hard to say "I don't like it" when you're still in the chair because of the urge we have to please everyone. But no hairdresser wants you to be displeased with your hair!

      Also, certain colours wash off and get a bit duller easily (my pink does, I can't keep a bright pink for very long), so try washing your hair many times?

      Good luck!

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