1990s-Style Bras and Underwear Perfect for Getting Your Tomboy On

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Summer is the perfect time of year to wear as little clothing as possible, don’t you think? If you’ve been eyeing the vintage Marky Mark-inspired underthings that are everywhere right now, boi, do I have some treats for you.

Sports Bras

1. Stussy Cross-Back Bral 2. TomboyX Striped Bra 3. Chonies Marbled Bra 4. Chonies Purple Haze Bra 5. Wildfang Cross-Back Bra 6. Old Navy Running Bra

These bras are soft, comfy, and super babely on their own or peeking out the side of a tank top. If you see a lady wearing one of these and your mind doesn’t go immediately to getting stoned and wrestling sexily together, I really don’t know what to tell you.

Boxers and Shorts

1. Play Out Graffiti Briefs 2. Wildfang Basic Briefs 3. Chonies Camo Brief 4. TomboyX 4.5″ Trunks 5. Play Out Wired Briefs 6. TomboyX 2.5″ Shorts

Whether you prefer flaunting all the bikini line you’ve got or a slightly longer leg, these undies are peak Aaliyah-style hotness. Sigh.

Embellished Bras

1. Missguided Mesh Bra 2. River Island Floral Bra 3. Toru and Naoko High Neck Bra 4. Sugar Thrillz Blush Bra 5. Wildfox Floral Bralette 6. Missguided Triangle Bra

Feeling more femme? Try pretty/sporty styles that wrap around your waist, or have a more vintage feel. This ain’t your grandma’s bullet bra (though TBH, I’m sure hers were great too).


1. Missguided Mesh Panties 2. Torrid Pink Cheekies 3. River Island Floral Thong 4. Calvin Klein Basic Thong 5. Missguided High Side Mesh Panties 6. Torrid Black Cheekies

Mesh, and thongs, and lace, oh my! Oooh… oooh… oh my.

Sets and One Pieces

1. Topshop Sporty Set 2. Boohoo Cutie Set 3. River Island Onesie 4. Torrid Lace Set

Finally, if separates don’t satiate you, you can double your pleasure and your fun with a super foxy one piece or set.

Alright, I’m going to take a cold shower now. Happy shopping!

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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 52 articles for us.


  1. Buying a new sports bra is literally on my real life to do list in ink. Also, I found Aaliyah very “confusing” back in the day (confusing = heart eyes) and I tear up every year on her birthday when the DC R&B stations play her stuff back to back.

  2. I have like 40G boobs-would those bras work for me? I currently have a fucking underwire sports bra from Lane Bryant that holds the girls up, but its UNDERWIRE. *cries*

    • The impression I get is that these are more decorative lounging bras than high-impact support ones; I’m sorry, fellow big-boobed friend!

    • I cant recommend the panache underwire sports bra enough. It is underwire but is the most comfortable and only bra I can wear. I wear a 32G, my friend wears a 38FF (UK sizing), and it is awesome. You can sometimes find them on ebay in old colors for less than full retail price. I don’t recommend the underwired version, it isn’t supportive enough and gives me chest pain. I hope this can help you, my life has seriously been changed by this bra.

      • I’m seconding Madeline. Panache is the bomb. I wear a 32H and I can actually run in that bra without feeling like I’m being kicked in the chest repeatedly by the weight of my own rack bouncing. Just be sure to choose the correct size before buying off ebay: no matter how great this sports bra is, it will not be comfortable if it’s the wrong size.

        Erica, as someone who used to work in a bra store as a fitting assistant: underwires are never the problem unless you have some sort of healing lesion right on the part of your body where you underwire runs. The problem is almost always the fit, although in some occasions it can be that the style is an incorrect choice (ie, certain styles may be better suited to some people based on whether or not they have long or short torsos, boobs closer together or further apart, high or low sitting breasts, etc) or that the bra is so cheaply made that the wire is busting out. I had so many people ask for no underwires and be staunchly against them when the real issue was that they were wearing a bra in completely the wrong size. TL;DR get fitted from a store with knowledgeable employees (but beware, not all bra store workers are knowledgeable), if you can, or read up on the internet about it and fit yourself for free.

    • I live the torrid life and I also have big boobs. I’ve gotten very into their bralettes (not for sports-bra-ing unfortunately) but they have beautiful styles and they are SO comfortable. I feel like they don’t keep my boobs up in like the perky underwire way, but once you get past that and embrace the heavy boobs lifestyle, it’s not a bad look.

    • If you’re looking for an actual sportsbra i can’t recommend the “shock absorber” highly enough!

    • Same, honestly. I wish plus-size folks had nearly as many clothing options as straight-size ones in the first place!

  3. See this is why I wish liked boxers and but I always find them so uncomfortable. I think I’m doomed to wear briefs for eternity

    • I thought that they’d be good too but I’ve come to the conclusion that I’m the wrong shape. I did a friend survey and everyone who isn’t the old classic hourglass shape, seems to have no trouble with the way they fit but if you’ve got a narrow waist and wide hips, boxers and boy shorts turn turn into bum suckers.

  4. I’m surprised Girls Will Be Boys boers didn’t come up – they are in my opinion WAY more comfortable than TomboyX, which has too many seams. GWBB are my all time favorites. Another good brand is Focx from the UK. Check them out!

  5. I love American Eagle’s aerie boybriefs, which had cheap shipping and a sale on when I bought them :D

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