Find Your Fit: The Tomboy Femme Breaking Past Polos for Work

Find Your Fit is a style advice column helping real queer people find the masculine, butch, and tomboy styles that make them look and feel hot.

Hi Mika! I’m a tomboy femme who’s been stuck in boring clothes in the last several years looking to break out of the funk of wearing nothing but work polos and old Navy pixie pants every day. I work in college admissions, but having a baby face I always wind up looking more like a tour guide than a professional.

I need a work style that feels more professional and grown up, but still shows off a little flair and queerness. I love spicing up normal outfits with funky little pieces like this Olivia Burton bee watch.

I’ve been following find your fit for a while and have started to pick up several staples you typically recommend, especially for my causal style (I’ve recently aquired plenty of black skinny jeans/leggings, black leather jacket, an oversized asos denim jacket, some white Chelsea boots and some loafers).

For Christmas my beautiful wife got me the Tomboy toes barrister’s boots in light brown, but that made me realize, I have nothing but jeans style them with! I want to use these boots as a centerpiece for a new work wordrobe.

I have a few specific needs: pants that can be styled with the boots without feeling like I’ve had to size up for a baggy fit, shirts/jackets that can go along that fit without allowing for that horrible boob gap, and any bold accessories to go with (also on a budget? Because like I said I work in college admissions).

Some style inspirations are Blake Lively in A Simple Favor (but dressed down a little) and Ashlyn Harris (when her hair was long).

Thank you so much for these specifics! To tailor to your specific submission, I want to do things a little different than usual. I’m going to use the watch you sent me as well as the boots to style all three outfits. I think what you want is totally doable and can happen within budget as well!


1 / Pants
2 / Shirt
3 / Cardigan
4 / Boots
5 / Bracelet
6 / Necklace


Blake in A Simple Favor is perfect, but I want to make it a little more tomboy and a lot more casual. To do this we’re swapping the usual heel she’d wear as well as the blazer for something more casual, but I want us to retain the color scheme as well as the texture.


For all these fits I want to start from the most dressed up (this one) to the most casual; I think the shoe you want to center all these looks around is very flexible in that way. I want to show you a full range of outfits for you to build a wardrobe that doesn’t feel repetitive or like a uniform.

For this first fit I started at the trousers. These pants from UNIQLO are super affordable as well as stylish; if you’re looking to get a bunch of different trousers for cheap, they’re a great option. This pinstripe pant brings you that dapperness Blake pulls through the movie. The ankle length works great with loafers (since you just got some) as well as boots. You can pair these pants with pretty much any top, but since you want to incorporate shirts more I went with this long-sleeved blouse. Sadly the button-gap situation with the shirts, isn’t something we can really control for with fit; But Doreen wrote about some ways to deal with this not too long ago!. Before I had top surgery and when I used to wear more shirts, I’d stay away from structured or fitted shirts and get pieces that were flowy and or of thinner fabric. This way they don’t tend to stick to the body and consequently cause the boob gap. I want you to wear this shirt untucked to balance the outfit out. If you want to experiment, maybe try a french tuck? But I would stay away from a full tuck especially if you pair it with a jacket or in this case this long cardigan. I don’t want you to look TOO dressed up; just the right amount. For accessories I picked this cool ring set from Topshop and this necklace from Oak and Fort. Both have amazing affordable selections of jewelry. If you wear a necklace with this shirt, button it all the way up or at least most of it. If you’re going to center your new work wardrobe around the boots, I’d also recommend gold accessories since they match the tones of the boot better!


1 / Shirt
2 / Trousers
3 / Jacket
4 / Boots
5 / Rings


We did Ashlyn before, but definitely not throwback Ashlyn and/or long hair Ashlyn. During 2013-2016 she was pulling a lot of formal looks as well as incorporating some more dressed up elements into her more casual fits. Something I really love about Ashlyn’s style is the way different pieces create a good silhouette. When you start wearing a baggy look in more formal or dressier clothing, it helps to keep in mind that even if you are trying to go for that square shape, it’s good to move in triangles, meaning things should taper in and out. The right balance of those makes you look intentional rather than like the clothes fit too big on you.


I started putting this look together with the pants. These high-waisted pants from ASOS are a great fit for shirts and t-shirts. You can wear them high up and create a sort of baggy taper and get away with wearing any sort of oversize/square top untucked while still looking sharp. If you hate the belt, just take it off. You can show ankle or not, these pants are super flexible and have that baggy but fitted look you are looking for. Pair these with this shirt from Wildfang (same thing as the previous shirt). The fabric should fall more naturally on your body so hopefully you won’t have the boob gap problem. I’d recommend that you button it all the way up, just like the previous top. Since you just acquired some new jackets, I linked to a biker jacket from ASOS, but you can just pair it with whatever leather jacket you have. This adds that edge Ashlyn always brings to her looks, but still keeping it dressy. Pair it with your Olivia Burton watch and some rings or if you’re feeling it this cute bracelet from Oak and Fort.


1 / Jacket
2 / Sweatshirt
3 / Jeans
4 / Boots
5 / Necklace


For this final Ashlyn fit, I wanted to do one more casual look. It’s still work appropriate, but flexible enough you could go to some plans afterwards. This is maybe closer to present Ashlyn than the previous one, but still on the same wavelength. The key here is color matching! Thinking in color can be overwhelming but sometimes simple is the best way to go. Using a base like black, and adding one other hue that is rich can be all you need to add that pop to an outfit.


Because your boots are so cool, in terms of both shape and color, I wanted to build you an outfit with that in mind. I started this fit with the jacket. This denim trucker jacket brings that inner bad boi out and at the same time creates some dimension for a very monotone look. I linked these ripped skinny jeans from ASOS but you can just use the black jeans you recently got or even the leggings! Wear it with a baggy top, or in this case I picked this two-tone sweater from Oak and Fort. The color is super rich and connects well with the boots. You can also wear this with just regular jeans or any sort of neutral bottom. To finish up, add some accessories; you can use your watch again and add some rings if you want as well. Because of the neck of the sweater a necklace could be an extra touch to finish up the look if it still feels a bit flat!

For help finding your fit, write to mika [at] autostraddle [dot] com with a little about yourself, your personal style icons, your size(s), and three or four selfies in your current favorite outfit(s)!

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Mika is a venezuelan art director, designer, stylist, and recognized funny friend. He has previously worked at the Walker Art Center (MPLS), 2x4 (NYC) and Rumors (PDX). You can follow him on Twitter, Instagram or check his website.

Mika has written 28 articles for us.


  1. As soon as I saw the header image I went IS THAT AN OLIVIA BURTON WATCH? Because I’m in love with their designs and I want to get at least five of them, even if I hardly ever wear watches.

    I love this more specific approach of building styles around items they already have!

      • But are they comfortable? I’ve got some that are similar and I adore them but they are simply hell to wear. My feet despise me after.

  2. Also! Also! Also! if you are looking for shirts that fit without a boob gap, that’s exactly what Peau de Loup was created for.

  3. @mika and the poster: this is perfect, this is exactly the style I want, too! Thanks to you both.

    Boob gap is the WORST and don’t get me started on being both very tall AND proportionally busty. Ready-made shirts that fit everywhere they’re supposed to are few and far between. It’s hard to keyword search, too, because each brand seems to have its own vernacular (see “curvy” meaning something totally different everywhere it’s printed). In case it’s useful to anyone with similar proportions to me, J Crew’s “tall curvy” shirts fit pretty well, although an extra hidden button would be nice, and ASOS has a “tall fuller bust” line (and standard and petite fuller bust), although I’ve found the quality of their clothes really lacking.

    @malloreigh !!! Wow I have never heard of this brand but I can’t wait to try out some of their stuff!

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