Did you know that American author Willa Cather used to dress in men’s clothes occasionally and sometimes went by “William?” Her sexuality has long been speculated to be lesbian, but this gender non-conforming behavior isn’t well known or much discussed, which I think is unfortunate!

I used to hate shopping and looking in the mirror. Now, I love it. Okay, not completely without reservation – I’m no Narcissus (the guy, not the flower) – but I certainly don’t make furtive glances in the mirror like I used to.

Genderqueer and non-binary folks can (and should) wear whatever they want – more “masculine” or more “feminine,” neither, or both, or alternating…  And I have owned and worn some great dresses… I loved my 5th grade graduation dress (a Gunne Sax from the factory store) and my junior prom dress in particular. But… my heart will always belong to jeans and a t-shirt.

Black and white photo of a young woman with blonde hair, in right profile
My junior prom dress.

Jeans and a t-shirt (“teenage boy”) are what have always felt the most comfortable to me. Sadly, these are not considered “business casual” even at a large, public research university. And certainly not for a 40-something middle manager-type person. Nor are jeans and a t-shirt appropriate for dinner with the in-laws or other types of activities generally categorized as “not running errands or walking the dog.”

So, a lot of polyester pants from Old Navy and various other not-frilly very much not-cotton items filled my wardrobe until I hit around 40. That was when I ditched the clothes and shoes I was never really comfortable in and started dressing more like “me,” both at work and in the rest of my life.

I want to call out some “elders” in the dapper and “masculine of center” clothing space that were instrumental and inspiring in my clothing journey. Qwear, DapperQ, and I Dream of Dapper – plus a host of others who posted on Twitter and Tumblr, sharing their outfits of the day – gave me the confidence to find my “me” wardrobe. They showed off their button-down Oxford shirts, bow ties, pants and shoes from the men’s section. Tips on shopping and accessorizing were shared and a variety of body types and sizes were featured.

There’s a difference between wearing menswear-inspired women’s clothes and wearing men’s clothes. Pockets, for one. But also the cut. Women’s clothes emphasize curves and collarbones and cleavage. I’ve never really liked wide-necked shirts, why do all women’s shirts have these huge, open necks?? It seems like there’s always a frill of some sort. Frills are not for me. And the color palette of the men’s section is much more my style – dark blues, browns, maroons, plaids (my favorite color!).

And have I mentioned I’m 6 feet tall? Yeah. Finding comfortable and not outrageously priced women’s pants long enough was a tall order (see what I did there?). Shifting to the men’s section gave me the option of shopping by waist size and length rather than the random vanity sizing numbers that women’s clothes come in (am I an 8 or a 16???). Plus, pockets. Also, I just really like how I look in “men’s clothes.”

It can be a bit scary shopping in the men’s section for the first time. But I’d been shopping there now and again for ages already so it was a relatively easy leap to trying on more clothes. Also a plus: Target is my usual go-to (mostly for shirts). Their dressing rooms aren’t divided by gender, which makes trying on clothes easier – you don’t have to go from the men’s section over to the women’s section to use their dressing room because stores generally don’t really like female-looking people in the men’s dressing rooms (not cool!).

Transitioning to men’s clothes for work has been amazing. I am so much more comfortable – both physically and mentally. Pants from Old Navy still fill my closet – but from the men’s section now and thanks to Target, plaid button up shirts are my staple.

I’m guessing a lot of my co-workers assume I’m a butch lesbian (a thing that’s happened a lot in my life, which I don’t mind, but I don’t want to mislead folks), though some know I identify as genderqueer/non-binary. When I’m not at work, I do still tend toward the teenage boy … jeans and a t-shirt, plus hoodie when it’s chilly or cargo shorts (long live cargo shorts!) and a t-shirt when it’s hot, with polo shirts and button ups thrown into the mix to not look too slovenly.

While I tend to stick with Old Navy, Target, Marshall’s/TJ Maxx, or Crossroads (second hand clothing store), in the past decade, there have been some amazing things happening in fashion for assigned-female-at-birth non-binary or “masculine of center women.” Dapper Boi (I love their jeans and swim tops), Flavant Streetwear, Wildfang, TomboyX, Androgynous Fox, and Hautebutch.

I still get hung up on work-appropriate hot weather clothes and formal wear for things like summer weddings (wool suit = sweat city; though, my blue pinstripe seersucker suit I donned for my niece’s wedding worked out well, and here’s what I’m planning to wear to another niece’s wedding next week).

Mirror selfie of a genderqueer, non-binary woman in a blue and white pinstriped seersucker suit, black floral shirt, and orange bow tie.
Summer wedding duds, 2017
Selfie of a genderqueer non-binary woman in blue pinstriped seersucker pants, a white button up shirt, yellow necktie, and a navy blue waistcoat.
Summer wedding outfit 2018










Swimwear is also weird. Though, “boy shorts” as a thing in the women’s section have been lifesavers also, board shorts. Swim tops like Dapper Boi’s Swim-Sport Compression Bra are awesome, and I’ve had luck with Land’s End mix and match swimwear – all hail the “tankini” top in a plain black or blue.

Changing the way I dressed had a deep and immediate impact. Suddenly, I liked looking in the mirror at myself. I liked shopping for clothes – both in person and online. Shout out to my college roommate and forever friend, Colleen, who helped me shop for some basics to build a look I was calling “preppy dyke.” Come to think of it, that’s probably still a pretty accurate description.

Preppy dyke aesthetic.

Anyone have any other hot tips or experiences for clothes shopping as a female-assigned-at-birth person looking for masculine of center clothes?


I just discovered an AMAZING Facebook group: Butch Fashion Club. There are so many awesome butches in a range of ages and body types!

There are a growing number of clothing brands that design for gender non-conforming folks (most of which are far too fashionable for me). Check out “12 Gender Neutral Clothing Brands You Need To Know About” and These 5 Gender-Fluid Fashion Lines Are Changing the Game if fashion is your jam.

2 thoughts on “What (Not) to Wear?

  1. T-shirt and jeans 4ever. Like it’s written in my genes…
    Read a bunch of posts – all wonderful!

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