3 Tips for Mastering Button-Down Shirts When You’re Busty

As a dapper woman, I always feel my best in a crisp button-down. Check out my closet and you’ll see that I have more of them than slacks and cardigans combined; I’m determined to have them in every color and pattern imaginable!

Most of my button-downs come from the men’s section, so they’re not made for busts like mine. In the past, that meant crossing my fingers every time I tried on a new shirt, thinking, “Please, please, please, let it close over my chest!” But luckily, with a few years’ practice and perseverance, I’ve learned some helpful tips. Let me drop some knowledge on ya!

If at first you don’t succeed, try a different brand

Me looking awesome in Kirrin Finch / Photo by Iqra Shahbaz

When I was first coming into myself and my personal style, I tried everything from the women’s section, men’s section, and even the boy’s section (where I got a few looks from concerned moms). Through trial and error, I figured out which brands work for me and which don’t; off-the-rack names that give me minimal to no bust-area issues include Uniqlo, American Eagle, Penguin, Old Navy, Calvin Klein, Scotch and Soda, and Bonobos. And of course, I have to shout out to Kirrin Finch and Peau De Loup, both of whom make menswear-inspired button ups specifically to fit women.

In my experience, American clothing tends to run larger (especially in the armholes and shoulders), whereas European cuts (like at Scotch and Soda) or Japanese cuts (like at Uniqlo) tend to run slimmer or narrower. Personally, I prefer Japanese or European cuts for long sleeve button ups and Japanese or American cuts for short sleeve button ups. It just all depends on which cuts work best for you — and since personal style is a journey like anything else, you should try, try, try before you buy!

You deserve a good bra or binder

I always get a flatter silhouette by wearing sports bras and compression tanks / Photo via the author

The right bra or binder can help redistribute/reduce the look of your breasts under a tailored shirt. Minimizer bras, which are designed to redistribute breast tissue and take an inch or more off of your bust, are one option. Personally, I found that even those accentuated my boobs too much for my comfort, so I wear a sports bra that offers compression and flattens out my silhouette. Finally, folks who want to more drastically minimize the appearance of breasts should try a binder! Many of my gender non-conforming and trans friends swear by gc2b and Underworks to keep their breasts out of sight and out of mind. Always do your research on binders before using them, and make sure you use them safely!

Double-stick tape is your friend

Performing surgery on these gaping holes / Photo via the author

Have you ever tried on a shirt that fit perfectly… except for a gaping hole between the buttons around your chest? I have, and it sucks! For situations like this, invest in some double-stick tape; all you have to do is put your shirt on, apply the tape to the gaping area in between buttons, press down, and voilà! It should keep that area shut.

Photo via the author

One downside I’ve found to the tape is that it can come undone on softer or stretchier fabrics; for a stronger, more permanent alternative, try sticky back Velcro. And of course, the tighter your shirt is, the harder it will be for either option to hold it together — so try to use it on shirts that fit well otherwise.

Okay, that’s it! If you have any tips of your own, leave them in the comments.

Doreen Pierre a.k.a DapperPenniless is a fashion blogger and photographer based in NYC. She prides herself on looking smart and stylish on a budget and uses fashion to represent her confidence and individuality. You can follow Doreen’s fashion journey through her websites,www.dapperpenniless.com, www.youtube.com/dapperpenniless, and on IG @dapperpenniless.

Doreen has written 2 articles for us.

32 Comments

  1. You definitely look awesome in that first photo! I never even knew binding was A Thing until I saw it recently on here.

    Now, I am depressed because Backwater UK is not the place to find anything remotely useful in this area, international shipping is pretty much out of my price range and I don’t fancy getting whacked with extra customs charges either 🙁

  2. You can also sew snaps to the space(s) between buttons that tend to gap. I did this to a shirt that fits in the sleeves and is kind of tight across the shoulders and chest (I liked the pattern a lot and they didn’t have it a size larger)…and it’s still small at the shoulders, but it doesn’t gap! Since I only sewed the snaps to the inner layer fabric on the button placket, the snaps don’t show from the outside.

  3. You should /always/ get your flannel from Duluth Trading Company. They make three weights, in a variety of colors. All are reinforced across the back and shoulders for people with breasts who like to do things. I am a skinny-ish 34/DDD with a long-ass torso and a medium (large to XL in most brands) fits me with room across the chest and down the trunk. Some varieties include a nifty little hidden extra button across the bust that prevents gapping when you use your arms. All shirts include a little microfiber eyeglass cloth hidden under the front of the button placket (useful if you are bespectacled, like me). It’s about $50 a pop, but they are so unbelievably worth it and are well made.

  4. I put in a vote for American Rag as an option to try. I have a pretty big bust, and wear their shirts to work all the time, and they’re only $30 a shirt from Macy’s. And yea, I use a safety pin from the inside, through just one layer of the button strip to solve the gaping button problem.

  5. what if you don’t want to tuck your shirt in?

    Besides having issues finding a shirt that fits both my boobs AND my shoulders correctly, when I do find that miraculous piece of clothing, it looks like a dress. I always have to tuck in. No casual shirt wearing for me.

    Any tips?

  6. I second everything the article says. I would also recommend the following brands: Theory, Ted Baker, Hugo Boss (regular fit), John Varvatos and Bugatchi. Most of these are a little pricey $50-250 (depending on where you buy). I personally love to shop at Nordstrom Rack–great deals for good quality clothes. All of these fit the bust pretty well, are easy to tuck and look great.

  7. I like the article, but I quite like being busty. I just wish there were shirts we could wear without hiding our big boobies. You know, still androgynous, without hiding anything with a bra. I couldn’t wear a binder either.

  8. I bought my first binders because of this article (gc2b) and it was the best thing I’ve done for myself in a very long time. Sport bras always give me headaches and I thought binders were only for trans folk but I got the confidence a month ago and it’s amazing for my confidence.

    Thank you!

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