How to Buy Shirts: An Introduction

1. The Glorious Versatility of the Long-Sleeved Button-Up Shirt: As you may have gathered, the unofficial butch uniform is button-up shirt with a (white, black, or matching) T-shirt under it.  This outfit offers both comfort and versatility.  Want to look more casual?  Leave the shirt unbuttoned.  More formal?  Tuck the shirt in.  Attending your gay ex-boyfriend’s wedding?  Throw on a tie. 
2. Brands: Certain men’s brands tend to be a little roomier in the hips and chest, and are thus friendlier to many female figures.  You’ll have to experiment on your own, but a few favorite dyke brands are Calvin Klein, Kenneth Cole, Material London, and LL Bean.  Banana Republic and J. Crew tend to favor the slimmer-hipped bois, as do Alfani and Van Heusen.            
3. Women's ("Ladies'") Shirts: To Look or Not to Look?:  It may be worth looking at women’s shirts by designers who are lighter on the frill factor (e.g., LL Bean; Eddie Bauer; Jones New York).  But beyond a few select brands, women’s shirts tend to disappoint the butchier members of the fairer sex, and you’ll spend hours futily searching for the one item in the store without lace or pearly buttons.  We've all been there.  
4. Sizing: The centrality of the long-sleeved, button-up shirt to the butch wardrobe means it’s essential that you buy shirts that fit.  Men’s shirts are usually sized in one of two ways: (1) S, M, L, XL; (2) using actual numbers.  Where (2) is employed, you will see two numbers.  The first refers to collar size, and ranges from about 14 to 18 1/2 (in half-inch increments).  Many sales clerks at Macy's, Nordstrom, etc., will happily measure your neck. 
5. Fit: Your neck measurement is useful, but not dispositive, because of—you guessed it--the breast factor.  For example, my neck is 15 inches, but the smallest shirt size I can wear without popping off buttons is a 16 1/2.  If you're a buxom butch, avoid slim-fit shirts, as these are even smaller in the chest.  The second number you will see refers to sleeve length.  The most typical sizes are 32/33, 34/35, and 36/37.  Even a 32/33 may be too long (this is easily masked by rolling the sleeves, which has the additional advantage of suggesting a serious work ethic).  Sleeves should extend to the base of your thumb.  Perhaps because bra sizes are also in the 30s, I spent my first months in menswear trying on 36/37s, having somehow concluded that 36/37 was a chest measurement.  I still own some shirts with way-too-long sleeves to prove it.  (And here’s another tip: don’t worry about what the numbers say.  They’re going to be different for you than for a guy, because you are a chick, and have boobs and hips.  Maybe you’re a 17, and your dad is a 17, and you think he’s fat.  Don’t worry about it.  The measurements mean different things for each of you.) 
6. Color:  One of the best things about being a butch is that you’re still a chick!  (Well, if you're female-identified.)  Or genderqueer!  Hallelujah!  This means that you can get away with wearing a wider variety of colors than most heterosexual cisdudes would dare to sport.  Have fun with it—try all kinds of different colors, and feel free to match your button-up shirt with the T-shirt you’re wearing underneath it.  No need to stick with white T-shirts every day, either.  Brands like Mossimo (cheap, awesome, stocked at Target) and GAP make men’s T-shirts in a wide palette of colors.  These make good undershirts because they’re thinner and cooler than those thick, cheap run-of-the-mill shirts made by brands like Gildan.  I like American Apparel, too (on those, the sizing runs small, so buy a size smaller than you normally do).
7. Conclusion: I'll post more shopping tips in the future (as well as waaaay more details about shirts), so comment or email me your questions.  I'd also love to hear what shirt-shopping tips you can offer! Oh--and here are some pictures of shirts I like.

      

Here's a maroon Kenneth Cole Reaction shirt. I like the subtle striped texture, and tend to get a lot of compliments on this one!

     

I've been loving tattersall lately. LL Bean is especially nice because you can order your *exact* sleeve length (as short as 31", I believe) and collar size.

      

This is a little number from Material London. I like it because it goes equally well with jeans or black slacks.It's got black, maroon, and dark blue stripes