Question: What Should Girlish Boys Wear?

Someone asks…

I’m a straight, girlish boy who has always dressed like a regular guy (usually in khakis and blue shirts).

I would like to be more open, but in contrast to the well-established tomboy look there doesn’t seem to be a consensus about how girlish boys should dress. I’m middle-aged and work in a place where business casual is the norm, so I need to look fairly professional.

I want to avoid the stereotypical gay guy look because it’s not me. Suggestions?

Please post your response in the comments below.

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Posted by on April 22nd, 2015 at 08:00 am

Category: questions 6 comments »

6 Responses to “Question: What Should Girlish Boys Wear?”

  1. Jen Durbent

    I’m in the same space.

    I’m mid 30s, so age appropriate garb is a thing.

    I paint my nails, dye my long hair, and wear colorful shirts, socks, sneakers. It’s subtle. On some days, I pull off women’s jeans, but not regularly.

    I wish I lived closer to a big city, some CD folks I know dress fully at work some days. But it’s a compromise where I love in the US.


  2. Anonymous

    Three quarter sleeves and slim dress pants? It is really trick for guy to girl fashion. I am much more used to the oppositie.


  3. Anonymous

    This takes an intro so bear with me as I appear off topic:

    I am dfab and transmasculine. I, like many trans guys, often get mistaken for a lesbian. Because lesbians look different and dress different and act different than guys do because they’re not guys. They’re women. And a lot of transguys are used to acting like women.

    There are men’s clothes that butches and androgynous dfabs wear that transmen can have a hard time pulling off when trying to pass: plaid, jean shirts, “hipster” oxford shirts, funky patterns, very slim or skinny jeans (which tend to accentuate the crotch).

    You might get some ideas from butch lesbian and/or androgynous styles. I know, I know, those are dfabs looking more masculine and you’re dmab trying to look more feminine. But butches are walking the line between feminine and masculine, which is what you probably want. You WILL have to work to avoid the gay guy look, but as gender non-conforming people, most of us have to work hard to avoid xyz look. I think that the walk-the-line would work best for your professional situation, because (even though it’s dumb), a lot of professional places think that a male-passing person wearing things like really feminine dresses is not professional, even if the same item on a woman would be totally fine.

    A lot of lesbian styles that women pull off are actually clothes from the women’s section that happen to look pretty masculine. This might be what you want. The sizes will suck if you do this, but you’ll get a female cut and feminine detailing and will therefore probably not look like the gay men who buy their feminine clothes from the men’s section.

    Depending on your size, this could be easier or harder. If you’re slim, it’ll be easier. If you’re on the heavier side, it could be harder.


  4. Wilhelm

    I’m going to agree with the 3rd response. Look for women’s clothes that are masculine.

    I’m in my mid 40’s but look much younger. Severely underemployed after dealing with death/bankruptcy… very serious issues. The physical danger to my life made me wake up to my gender fluidity when I realized that the next day could be my last day. So I decided to open up to the world and stop hiding.

    I have no mannerisms in my voice, nor am I interested in that (I’m a typical cis-lookin/sounding guy, save I have a very undeveloped, thin “a-la- Twiggy” type body, and naturally feminine in the face. Also from the waist down I have natural inexplicably feminine curves since childhood, so I knew I could exploit that.

    I grew out my hair and intentionally picked a hairstyle that was actually neutral, but strongly suggesting femininity today – a 1920s flapper style Shingle Bob – yeah I know. It sounds severe, but it’s really not – some people will think you will look very “1960s UK Mod” look or perhaps like “one of the Ramones” – so it’s really gender neutral (plus back in the 1920s it was originally meant to make women look like boys – so it’s the original gender bender haircut – plus points for that).

    Then, the first thing I did was try to find my sizes for pants. Lots of math and reading allowed me to compare masculine and feminine body differences, and I started buying women’s slacks. Since your body is different to women, you will need to buy different sizes for pants compared to tops (pants will be surprisingly small sizes on account you have no big thighs and hips, but and “extra large” top for women will be in the small range for men, depending on how well built you are in your upper body. Shoe sizes will be a challenge. To US sizes your women’s sizes are one number higher (Size 10 men – size 11 women) – look for conversion charts on the webs.

    I found straight-leg slacks and corduroys at first and was very surprised as to how natural they looked on me. Almost disappointingly masculine. I wore them to work – every day, and fell in love with them (the best fitting pants I ever wore). Then I graduated to women’s stretch boot-cut jeans – again wear every day – I did not want skinny jeans as I thought that was overkill, but I did want to show my slight curves, so stretch denim boot-cut were chosen. The boot-cut jean is tight at the butt, and tight from hips to thighs, and then flares up below the knees, not as much as a bell bottom, but to a normal size opening as the cuff of the pant leg for men.

    I chose dark-indigo wash to have them look like 1980s jeans, and due to the flare they look a bit like 1970s jeans – so a nice “retro” theme, and I chose nice bright stitching in the back – you want your butt to look good, right? XD And I’ve been told so (somewhat creepily) by STRAIGHT male friends of mine (perhaps they’re not as straight as I thought XD )

    Again, sounds like it won’t work (bulge anyone?), but you will be surprised how well they fit (stretch- remember?). No need for gaff or any of that crap. Not a bat of the eye from the public. Cute rear-end and that “bulge” fear is totally misplaced, unless you happen to be abnormally large down there.

    Part of it is that in modern times we are too used to rocker type young people wearing tight jeans already – so tight jeans will NOT look so far out of place as you think. Again – the best fitting pair of jeans I ever owned – never going back to male jeans. Not a negative comment from anyone. Just compliments.

    OK so you got the lower half covered. Look for “masculine” top styles for women. For the top I am currently looking for safari style 3/4 sleeve or roll-up sleeve linen shirts; they are fitted (waist cut) and will have small details that say “fem.” For work wear poplin/cotton button down shirts. They will be fitted as well – enough to create a slight waist if you’re thin. If I’m already wearing feminine hair and women’s jeans without raising too many eyebrows, then wearing one of these shirts should be a walk in the park.

    In fact men in Asia prefer fitted shirts if you look closely. The Asian Men’s fitted shirts have a “masculine cut,” biut of you look closely it is very similar to women’s cuts – basically you have two extra stitching lines at the back or even the front of the shirt – which Western male shirts do NOT have at all. This makes the shirts fitted to the body and create a curve. For female shirts the narrow point is the waist – define as being righ above the navel -for BOTH men and women (read Wiki on that). The button-down shirt bottom is flared for women’s styles, so you can choose to wear the bottom over the pants (more feminine) or inside the pants as you wish.

    For shoes you can go gender neutral by getting “Penny Loafers” which basically are – you guessed it- a masculine style for women. Asian women, and in particular Japanese school girls wear these a lot – they are basically an English style shoe for women. Just beware that getting shoes in your size may be very difficult, as it is nearly impossible for most men. Some loafers are fantastic – choose a patent leather look that will be very dressy and feminine or a matte finish which will look more “schoolgirl” and perhaps even indistinguishable from men’s shoes – depending on which style you get – too many choices.

    What I describe above is a feminized work-acceptable attire, and as I wrote I’ve been doing it for 8 months without raising eyebrows. My hair is usually the focus of attention instead – and again- mostly compliments is all I get – whether I’m “one of the Ramones,” one of the Beatles, or a “1920’s flapper” is really in the eye of the beholder. Pair it with a black shirt and a skinny tie, talk with a Liverpool accent and you’re good to go. IMHO you will be appealing to both men and women alike – and I say so from experience, happily.

    Or if you look really young, break out the eye liner and you may want to go with an Emo look, which basically is just a long variation on the Bob hairstyle. But that may be considered far “too subversive” by your employer, because it’s more “dishevelled.” My Shingle Bob is very sharp (literally) and much more clean and polished.


  5. Cory

    Women’s clothes that are on the masculine side is great idea and I definitly want to try this out. Having not really shopped in the women’s section or stores before what is everyone’s suggestions on where to start shopping? I am late 30’s and in the Pacific Northwest of the U.S. My initial thoughts are Ann Taylor, Banana Republic, Nordstrom (maybe a little expensive).

    Thanks Everyone!


    Wilhelm replied:

    Yeah… the money, the money… big stumbling block (at least for me XD ).

    Ann Taylor has some really awesome stuff – but I’m looking at a Worthington button down shirt right now from JC Penney’s that I’m sure I’m going to get very soon (next week) which is probably 1/5 of the price of anything Ann Taylor makes in shirts and also a pair of capri-length jeans (it’s getting very hot where I live) from the same website. I bargain hunt.

    For shops like Nordstrom and Dillards – the key is specials – you can’t buy anything there unless it’s on special, and that requires luck in both Internet and in-person shopping – it’s basically the luck of the draw. But I love the quality of their stuff. Really worth the pain. Make a point to swing by the mall periodically and window shop – you have to, because when you see something, that’s probably the last chance you’ll ever get to buy it. Most items on sale are going, going, gone.

    I now understand why women shop the way the do and why they take care of their clothes that way too. Women’s clothes are constantly changing in style and what you find this week, you’ll never find again (I promise you). If you find something you really like in person or online, get back as soon as possible to buy more (pants blouses, etc) before they are gone forever. Buy in several colors (say brown, black and gray pants).

    For more casual ware, I ended up getting my jeans from JC Penney’s, believe it or not. Great bargains, go down from $40-50 jeans to $25 or so. I deliberately chose Lee’s because they have a more traditional jean shape shape – they know how to do sexy jeans better (avoid “mom jeans”). Stretch is the key here so look for cotton + 1% spandex denim or similar. Same rule applies to slacks – stretch will adapt better, as you legs and hips are “thinner” relatively speaking while your “belt waist” will be bigger that usual (proportions between men and women are different, and all that jazz)

    Honestly, now I do a lot online, because you really have to look and look and look until you find something you like. The trick is finding your size and your favorite brands before venturing into Internet shipping. I do like shopping in person, but it takes 10 times longer, and you’ll be paying for gasoline anyways – might as well pay it on shipping!

    The shoes are a bear of a problem to tackle – so getting those large sizes is definitely an Internet job – bargain hunting DSW, and the like. Sometimes manufacturers discount soon to be discontinued items. I got my eyes on an incredible pair of black patent boat loafers with a white masculine style rubber sole and heel – a real gender bender, and this is a discontinued item. Often this works to your advantage because large sizes in shoes are difficult to sell also – so there will be discounts there (the $120 patent penny loafers come down to $65 at the manufacturer’s website and $60 at the Nordstrom website – the Internet allows you to compare the item across shops).

    Underwear – that is always something I shop in person – always. It’s very personal, and I find it easier, oddly enough. I guess it’s because I started doing this before the Internet was important XD


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