The Style Manual: The Dress Shirt

Feature image via DapperQ

Everywhere — from Paris catwalks to grocery store checkouts — is filled with ideas about how to dress. They’ve got rules and handsome men clones galore, but what do you do when they’re not talking to you? Sure you can ignore them, but even dapper queers, fancy bois and dandy ladies need some help now and then. With that in mind, Anita Dolce Vita of dapperQ rounded up some experts and set out to create a style guide for us.


Header by Rosa Middleton

Chapter 1: The Suit

Part 1: An Introduction To Suits

Part 2: Classic Rules, Sizing and Fit

Part 3: The Fashion Council Answers Your Questions

Chapter 2: The Shirt

Part 1: Finding Your Dream Dress Shirt

Part 2: The Fashion Council Answers Your Questions

Welcome to Chapter 2 of our Style Manual for masculine gender nonconformists and transmasculine individuals (here on referred to as dapperQs).


Blake Calhoun

Esquire magazine states that a quality white dress shirt [at minimum] sits on the totem pole of necessity somewhere between a “belt and a toothbrush.” Yet, many dapperQs struggle with finding at least one decent dress shirt that fits.

So, what’s a dapperQ to do?  First off, you have to start from the start. We’ll walk you through some basics. Some of the vocab may seem a bit esoteric and trivial, but you can’t complain that you’re not finding what you want if you don’t know what you’re looking for. And besides, you can’t break the rules until you know them.

SHIRTOLOGY 101: Vocabulary

Section 1. Anatomy of a dress shirt


via DapperQ

(1) Collar (2) Yoke (3) Sleeve (4) Front Placket (5) Pleat (6) Dart (7) Sleeve Placket (8) Cuff

If you really want to nerd out about collars…

If fancy cuffs are your thing…

If you’re crazy about plackets…

And, if you want to know all there is to know about pleats…

Section 2. The “Rules”

Menswear experts agree on the following fit guidelines:


Your shirt should fit exquisitely: not too snug and not too billowy. When your shirt is buttoned, there should be no “pulling” and the buttons shouldn’t be hanging on for dear life. While many dapperQs believe that wearing oversized shirts will conceal weight or make them appear more masculine, all of the menswear experts advise against wearing “boxy” clothes because it looks sloppy and adds bulk.


Sit down when you try on dress shirts. When in a seated position, your shirts should skim your waist, allowing for “eating” room. And again, the shirt should have some fit around the waist (close, but not tight).


So, the writers at Details magazine believe that the golden rule with respect to collar fit is that you “should be able to comfortably fit two fingers between your neck and the collar of the shirt when it’s buttoned.” Seems pretty straightforward. Except, GQ magazine states, “Make sure you can comfortably fit one finger between the collar and your neck. If two fingers fit, the collar’s too big.” I guess this means we have some leeway, which is a good thing for dapperQs.

Collar Style

According to Ivette and Crystal González-Alé, Founders and creative visionaries behind the Marimacho masculine clothing line for diverse bodies of all genders, “Your collar should complement your face. If you have a round face, you should wear a pointed collar; if you have a thin face, you should wear a spread collar; and if you have a long neck, you should wear a high collar.” Keep in mind: Collar points are the tips of the collar, spread is the distance between the collar, and collar height is how high the folded collar extends on your neck.


The cuffs of your shirts should fall between your thumb and your wrist.


Your shirt should be long enough to CYA when you’re seated. Avoiding plumber’s crack – yet, another reason to sit down when trying on shirts.

Section 3. Sizing and Fit 

Here’s where things get a bit tricky. Some of our answers are going to relieve a bit of your stress, while others are going to add to your existing frustration. One thing that you must know and be comfortable with now: Menswear is not really made to fit the average American cis-male body either. Cis males often have a hard time getting their neck sizes to match their waist or arm sizes, struggle with finding clothes that fit when they are “between sizes,” etc. NPR recently gave a graphic breakdown noting the differences between off-the-rack, made-to-measure, and bespoke suits and menswear blog Put This On produced a video detailing the differences between custom-made and off-the-rack dress shirts.


Sonia Oram in Custom-Made Blank Label Shirt. via Qwear

This is not to minimize the unique fit challenges experienced by dapperQs. But rather to encourage you to look into tailored and/or bespoke shirts which will be your best bet when finding the fit you desire.

One thing is certain: It doesn’t matter if you’re going high-end custom-made or thrift store chic, you definitely need to know your size. Yes it’s true, many off-the-rack dress shirts do come in sizes such as XXS – 4XL that can be grabbed by the handful and dragged into the dressing room with you. To streamline this process, dapperQ created a ball park size chart that translates basic boys and menswear sizes here. However, since we’re getting down to the nitty gritty, let’s talk about this kind of tag:


The first number (17) corresponds to your neck measurement and the second numbers (32/33) to your sleeve measurement. Do you know your size?  We’ve got a video to help you find out.

Be sure to check back tomorrow for answers to you questions from Anita Dolce Vita and her crew of experts.

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DapperQ is one of the world’s most widely read digital queer style magazines and is a preeminent voice in queer fashion and beauty. We inspire people of all sexual orientations, gender identities, and gender presentations to think differently about both queer fashion and beauty as art and visual activism, and ultimately have a deeper, more fulfilling relationship with style. In the words of founder Anita Dolce Vita, “dapperQ is a queer fashion revolution, one of the most stylish forms of protest of our generation.”

has written 35 articles for us.


  1. Even though I am currently testifying on Benghazi, I couldn’t help myself and comment on this post. I am always having difficulties with my fashion, as some of you have pointed out before, repeatedly, and this is just what I needed! I especially like that there are clear shirt rules. I like shirts and rules. Thank you for this post.

    • Is that actually the Mrs. Hillary Clinton commenting on this or just somebody using her name to comment here? And besides that, I have to agree with everything you just posted.

  2. This is perfect. I need to invest in some button-ups given that the only one I own is a hand-me-down oxford whose sleeves are way too short. But I wear it anyway because it’s a really nice one from Orvis. Damn my long arms!

  3. this is great! i really liked the suit 101, it was very helpful, especially the tailoring advice.
    actually, after that i got a suit from topman and had it tailored and i’m very happy with the result!

  4. Thank you!! I have been looking for the perfect white button-up for a while now, but only recently decided that it is high time to find one! :) So this guide is perfect!
    I am tall and pretty skinny and when trying on shirts I always end up either with big bulky shirts or shirts that are so short that they never stay put in my pants. I’m going to London in a few weeks and I’m gonna try Long Tall Sally.
    I will find that shirt one day. I shall not give up!

  5. I must admit to being so femme I read ‘dress shirt’ and thought ‘shirt dress’, so aside from that initial disappointment it was an interesting read. I work part time in a fancy restaurant where I have to wear a white men’s shirt and bowtie and I get kinda frustrated with the fit of the shirts, but I have to replace them so often I’m not really bothered about tailoring.

  6. I need to start checking boys dress shirts, my neck is so small it’s super difficult to find dress shirts where the collar actually fits (and the ones that do fit around the neck tend to expect you to be super skinny and so don’t otherwise fit my body)

    • kd15, we hear ya! This is a common problem, even for cis-males who have a large waist/neck ratio. Stay tuned tomorrow for more specific advice on brands/tailoring/troubleshooting. But, your best best will always be to go custom-made.

  7. What about short-sleeved dress shirts? I usually buy women’s shirts because they fit better, and am having *such* a hard time lately finding short-sleeve women’s button-down dress shirts. I’ve looked at H&M, Target, Ross, Old Navy, but only ever have luck at thrift stores. Are they just out of season? Should I wait until spring?

  8. very good information but all this shirts are for girls not for Men.
    thank you for the info.

  9. Interesting video. UIsually when I buy dress shirts I tend to buy all cotton ata size 16 collar because after a few washings there is shirkage and also just because the label says size 16 some times it is a little too large or a little too small.

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