my style: the art of sassy crossdressing

I mentioned previously that stylish ladies should rock ties more often, and I stand firmly behind that declaration. There are few things sassier than menswear inspired pieces, and I think everyone deserves to rock it out drag king style once in a while. It doesn't have to be a full cross, but stealing portions of menswear for ladywearing can be so much fun and add an interesting flair to your outfit. (Sidenote: the same totally goes for the reverse, but since I don't think there are a lot of gents reading my blog, I'll hold off on my testament to the awesomeness of crossdressing dudes.)

For example, today I was the bartender at the speakeasy my kitchen became for my lovely sister's murder mystery party. As a dapper 1920s gent, I got my cross on:

I wore this with black jeans because that was all I had at home, but a button-up, vest, and tie would look amazing with a pencil skirt for business wear. Or even with plain jeans for casual chic. A fedora is also an excellent addition to many outfits.

If you're dubious, or need a better example than me, I offer up that most sultry of screen sirens, Marlene Dietrich.

Image courtesy of Life magazine

Dietrich rocked a tux in every conceivable way. I don't know if I've ever seen a man who looks as stylish in a suit than she did (maybe Joseph Gordon-Levitt).

The most important thing to remember when you look into menswear styles is your own shape. Some bodies will fit well into actual menswear and more direct inspirations, while others might need a bit more tailoring and shaping to make a blazer, for example, fit like a dream. Personally, I'm mostly hourglass shaped, so a men's blazer that fits my bust will be very baggy around my waist, which I'm not a huge fan of. I need darting and structure for it to look how I want it to. It's one of those things that needs some trial-and-error or, as I like to call it, try-on-and-error!

Have any of you rocked it boy-style? Tips for anyone who wants to get her dapper on?

Don't forget that you can always ask questions and make suggestions in the comments or my askbox! And, if you like what you read, don't be shy about sharing it! E-mail/tweet/facebook/shout it out!


  1. I love everything about this post. Menswear is such a great look on women - and no, no one has ever been able to top Marlene Dietrich, lady was fierce.

    I'm much more of an Annie Hall, though. Menswear with just the right amount of disheveled. Wide-legged trousers and a perfectly tailored vest can hide a multitude of hip/waist sins.

  2. I LOVE this post, for several reasons!

    1. While both Jen and I are lipstick lesbians and prefer lipstick lesbians, there is just a classy sexiness when women wear mens clothing. And vice versa!

    2. I wish more people could think like you and I. Cross dressing is still such an iffy topic in so many areas and it's truly sad.

    3. I just love your blog. ♥

  3. @Gillie I wish more women felt comfortable rocking a menswear look; it really is so fun and flattering. I'm usually a wide-legged trousers and vest kind of girl, but I was really digging that tie. I might have absconded with a few...

    @Angela And crossdressing (in the menswear-inspired way) doesn't have to be mascuiline...I think that in a lot of ways the right sort of tailoring can really provide a great contrast that amps up femininity! And I totally agree; I don't get why people need to get up in arms about things that really aren't their business. Thanks ♥!

  4. Oh, Marlene Dietrich. OH, JOSEPH GORDON-LEVITT.

  5. @Nicki Foxy of the past and foxy of the present! Both rocking a well-tailored suit.



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