A Woman in Man’s Clothing: Part 2

The long awaited second part of the series. If you recall, I discussed the basic fundamentals of taking measurements, accessories, etc in this post. Now we’ll continue on to discuss some actual fashion Dos and Don’ts, including the difference if you want to pass as male or not. Also, tons of thanks to Penny for being one of my models–her build is similar to mine.

You might recall that I mentioned that I’ve got a trim waist, small upper body and respectable hips. The space in the trunk, so to speak, makes getting men’s pants a little bit complicated. Generally if you’re shaped like a man with little to no hip, you would purchase pants with your exact waist and inseam measurements (IE 29/30, in my case). Aside from it being extremely difficult to find waist sizes smaller than 28″ in men’s clothes (look in the boys’ section), you are also facing some complications in fit type. However, my solution to having a much larger hip size is to rachet up one inch each direction–in other words, I buy 30/31 or 30/32 (waist followed by leg length). This usually results in the manufacturer of the pants having allowed more crotch spice, which translates to space in the back for me.

First thing’s first: No pleats. Do not wear pleated pants unless you have absolutely no hip–the hip shape will unfold the pleats and make them look odd across your front. The same is true for an overweight male, it’s generally just a good idea to avoid pleats. Also avoid wearing traditional “girl cut” underwear, specifically thongs and bikini cuts. They will be horribly uncomfortable with the usual seam placement in men’s pants.

Now, if you just want to be comfortable and look good, you are looking for (in dress pants) slim fit, or “modern fit” depending on the brand. These will be more hip-hugging, are more likely to be made of a slightly stretchy material and usually have pockets designed to be slim. Avoid putting anything bulky in your pockets, and make sure they fit comfortably but not too loosely–a loose fit in “slim fit” pants will sag in weird ways. As you can see here, I’ve done a 28″ waist and 32″ inseam to allow for the shape of my hips.

If you are more inclined to want to pass as male, you will want to get a looser fit to avoid emphasizing hip shape. For this you want “traditional fit” pants, and should look for wool pants because they retain the shape of the pant better than polyester blends. If you have much hip, like I do, make sure you get the pants just slightly too big (IE my 30/32 trick) and let them hang on your hip rather than your natural waist. This also gives you room for underthings, including packing if you want to pass fully:20130727_115059
It’s very important if you are wearing nice pants to wear shirts that fit the same group. Tucking shirts in is better, and men’s shirts are usually designed to be long enough to tuck deep into the pant. Look for shirts without breast pockets, as these will just emphasize your upper shape. If you want to pass you will want a shirt that is not too big at all, because oversized shirts make it clear that you are wearing clothes not designed for you. A lot of guys have this problem too–they just buy whatever is close without picking the best fitting. If you’re small like me, neck and chesk size are going to be the most difficult here. I find it easier to look in the boy’s section for dress shirts. However, a “modern/slim fit” 32/33 14 1/2 shirt (which translates to a 32-33″ chest and 14 1/2″ collar) will fit me fairly well depending on the cut. You have to try these on–the manufacturer sometimes makes the arm holes weirdly shaped so that the shirt won’t be comfortable even if the measurements are right:


This shirt was an atrocious color but “fit” correctly. Except when I lifted my arms. Then it got tight and uncomfortable across the shoulders. By contrast, here’s a size 12 boy’s shirt:


“But it’s summer time, I don’t want to wear long sleeves,” you say. In which case, you have three choices. Polos, tshirts, or rolling your sleeves. Don’t do short sleeved dress shirts. Just don’t. The style is very “worker class,” and it’s even harder to find sleeves that will not make the average arm look tiny by comparison. There are lots of great tutorials on how to properly roll your sleeves, like this one:


Polos are great, but avoid big logos or images. Screen printed tshirts are accessible everywhere–but make sure that it fits closely without billowing. You can leave some polos untucked, but generally I would recommend tucking your shirt in and wearing a belt unless it’s a tshirt–and even then, consider wearing a belt. This will help keep the waist of your pants in place, so it doesn’t shift around with your hips–a vital step both to comfort and passing. Also avoid vnecks if you have any chest shape and plan to pass, because they will lend to the feminine air. If you’re just dressing for comfort, though, vnecks are totally ok.

Now for jeans… again, if you want to pass and have hips, it’s probably a good idea to get a looser fit of pant and let them hang on your hips. The same rules as dress pants apply, but for modern fit you will definitely want to avoid putting things in your pockets if you want to pass. Darker colors are easier to pass in, for some reason–likely because most womens’ jeans seem to be the lighter colors. Remember that mens’ pants can also have indigo dyes, so be careful where you lean. Try to avoid tons of holes, though a few dings are OK.
Personally, I like to do jeans with button-ups for a classy semi-casual look:


A few vital tips:
1. Never let your ankles show. Wear long black socks with black or brown men’s style shoes (dress or dress casual), or wear a pant leg long enough to cover your ankle and the top of your shoe even if you are sitting down.

2. Test drive the pants you try on by crouching. If the crotch of the pants bulges weirdly, the fit isn’t right. You’ll look oddly proportioned while sitting down if this happens.

3. Vertical stripes, never horizontal. They both slim you down and make you look taller, thus adding to the illusion.

4. Dark colors are great but bold solid colored shirts (or earth tone shirts with bright ties) will both grab attention, make you look professional in a cutting-edge sort of way, and draw attention away from other features.

5. A big wide-faced watch is a good accessory if you are likely to wear cuffed or short sleeves. Avoid thin-faced watches, as they go better with women’s clothing.

6. Wearing a ribbed tank or a v-neck undershirt can help hide bra lines and make shirts that are often semi-transparent (IE almost every men’s dress shirt ever) less awkward. If only guys would learn to do this.

7.  Iron your pants. Really.

8. Places like Target, Aeropostle, and H&M that cater to a “metrosexual” look are more likely to have smaller guy sizes and clothes that really lend to passing. Avoid really heterosexual stores.

9. Experiment! At least in the dressing room…


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