A Woman in Men’s Clothing: Part 1

This is going to be a multi-part article because it just needs to be… You could also consider this a guide for men of various sizes.

First, why wear men’s clothes? Or, more accurately, clothing assumed to be cut/made for men. Let’s start with the simple reasons. Availability of pockets. Sizing that makes sense and is based on physical dimensions rather than some arbitrary weight concept invented by whatever white middle aged man owns XYZ company. Necklines that actually have buttons all the way up and can accommodate a tie. Buttons that button in the right direction. History lesson, the reason we still have men’s and women’s shirts button differently is because women were expected to let their servants button them up. Because apparently buttoning our own shirts was too tiring…
And don’t get me started on shoes.

Generally speaking, many clothing manufacturers still assume that men want comfort and women want style. So even the most stylish mens’ clothes are designed to last longer and fit more comfortably, with less chafing, sweating, and general ick.

So, to begin with, our first lesson is going to involve the actual fitting of clothes. Now, I am somewhat short waisted and long in the leg for my height. I also have some hip to me, but almost no cup size to speak of.  Keeping my dimensions in mind, I also have involved several other willing models so that we can cover different body types. This is NOT a series of articles on how to pass as male–although I will throw in a few tips here and there to help with that. Instead, this is a series on how to shop on the other side of the store, for comfort, functionality and style. Also, as my wife likes to remind me, androgyny can be sexy.

Start by getting your physical measurements. You will need the following measurements for typical or partially custom-fit clothing:

Neck – Hold the measuring tape around the thickest part of your neck, typically where an adam’s apple would be if you had one. Add two fingers between your neck and the tape to make sure a tie wouldn’t choke you to death.

Arm length – The measuring tape should start right at your shoulder joint and end at about the crease between your thumb and forefinger.

Wrist – Measure the diameter of your wrist.

Head – Measure your head diameter at about 1/4″ above your eyebrows and roughly 1/2″ above your ears. That should be about the thickest part of your head, and where most hats sit. Even 1/4″ of diameter is important here, as hats can slip and slide with even a little give.

Chest – Hold the measuring tape tight around the thickest part of your chest (yes, including your breasts if you have them). Wear whatever kind of bra you usually wear to make this measurement, since the shirt will go outside of that. I prefer sports bras, personally, but that’s because I don’t have to worry about holding anything up. If you want to pass and have to bind or otherwise flatten breasts to do so, make sure you are taking this measurement with binding in place.

Waist – This should be your natural waist, so that means measure this right at where your belly button is.

Hips – This may be right across your butt or may not, but should be wherever the widest portion of your hips are.

Inseam – This is the hardest one to get yourself. You need to measure the inside of your leg from the side of your crotch (all the way up in the joint there between inner thigh and exceeding PG-13 rating) to the floor. Do not wear shoes to take this measurement. Mine is exactly 30″, for the record.


Now that you’ve got all of your measurements down, you’re ready to get started. In the next article I’m going to talk about actual clothing selection and choosing the right styles of cuts to fit you, both in dress clothes and in more casual attire. To wrap up today, however, we’ll talk some about accessories of the necessary variety.

First of all, let’s start with belts. Belts are a necessary evil that can make any outfit –casual, semi or formal) look nicer or just ruin it. It’s a fact that usually the smaller you are, the wider a belt you can wear. Generally I would say that if your waist is the widest part of your body, you want to keep your belt width below 1.5″ but above 3/4″. If your hips are wider than your waist you can do a wider belt, but anything wider than 2″ will have a hard time fitting belt loops and generally look more feminine anyway.

Consider suspenders if you have difficulty keeping pants sitting at your natural waist because of waist size. They will hold your pants up and, if you wear them over your shirt, can be considered a fashion statement. Suspenders are coming back when done right. There are also men’s shirt garters (like these from Men’s Wearhouse) that will keep your socks up and your shirts down, but under your clothes. Good for men and women of any size.

Next, and of a bit of interest, is the underwear. Men’s clothes rarely have a waist that makes sense with the thong or bikini cuts popular right now. Personally I recommend boxers for comfort, but there are also “boy cut” women’s briefs that don’t ride up too much. If you are planning on passing, consider boxer briefs. They have a shape that expects a package, and so are really weird on a girl with hips unless you have something to add to the front of them. However, a well placed deception looks best in close fitting boxer briefs.
Avoid the kinds of knits that will be uncomfortable on your skin. Woven soft cotton is wonderful. Satin feels good but will raise the temperature (not in a good way) on a hot summer day.

Moving onward, ties… Now, ties can be just downright fun, but I recommend avoiding very wide tie styles. Also avoid obnoxious patterns–stick to stripes, solid colors, paisleys, etc, but avoid very bright and “loud” ties (Mickey and Garfield, anyone?) that are designed more for casual fun than for formal attire. Silk ties are beautiful but tend to wrinkle, so make sure you don’t leave them tied. A mid-width tie is also easier to tie into unique knots, like the eldredge knot. The latter has been one of my favorite party tricks, so to speak. You can see how to tie it here.

Finally, hats. If your method for passing runs the way of the gangstah, you might consider a big thuggish ballcap. That’s not really my style, so I enjoy a variety of newsboy caps and fedoras. Places like Target carry lots of these right now, and they come in small (which is really medium) and size huge. Whenever I find one that fits, I snatch it up because my head is fairly small. This is where your measurements come in handy! If you want a nice top hat, for example, or a bowler, you will need your band size to order them. There will be a lot more on this when we come to the final part of this article, the part about dressing in men’s clothing (in period attire).

Keep reading next week for part 2: Style for the short and smaller than average…


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