JUST ASK KIPPY: Should I Wear Menswear?



Dear Kippy—
Do you give fashion advice? I’m keen on buying (and wearing) these J. Crew Bowery Wool Pants.

They seem classic and chic but I’m worried I will look like a man! I know some gals can pull of menswear without a hitch but I’m not uber-confident I can … But I still want to try! Thoughts?

Worried I Will Look Like a Man

Dear Miss Manly,

If you are worried that you will look like a man…Then you most certainly will look like a man! The reason that menswear is so sexy on some (and not others) is because the female who pulls it off must have the most tip top confidence in her feminine ways. It takes a self-assured person to engage in fluid sexuality. (Men who wear pink sweaters and women who wear vests are secure… So, for that matter, is Prince, who I would argue is the sexiest man alive…n’est pas?)

Speaking of sexuali-tay, I got into quite the debate with some playwrights recently about the describing a person as “sexual. ” Just what does that mean anyway?! The playwrights were a fractious group that evening! But that is a tale for another time!

Back to your dilemma. I would be more worried paying so much money for some pants that you’re going to have to take to the tailor. While I love to “take it to the tailor” (that’s a song, btw)—I love even more when ready-to-wear fits me just so. There is, however, a saying I find most apt for your quandary, “You never regret quality.” That is true with people, jobs, lovers, and clothing. If you think you’re gonna wear these sturdy looking pants and feel amazeballs in them, then BUY all means (wink!) … Purchase away.

However, if you fret that they will sit in your closet alongside other sartorial mishaps I would advise against. Did you know most people wear 10% of their clothing 90% of the time? And did you know that 87% of statistics are made up on the spot? Zing!

One last tidbit. When I worked in the fashion world (yes, this cool cat has led 9 lives!) I recall trying on some runway wear of Vivienne Westwood’s. My oh my. As the wardrobe people fussed and futzed over me, I succumbed to a strange and powerful calmness. It was the most womanly I had ever felt. Truly! The clothing fit me in a way unlike anything I had ever worn before. I thought, “How can I ever return to mass-made clothing?? Couture here I come!” Then I looked at my bank account and went back to shopping at Daffys.



Ciao for now,


About kippywinston

a cool cat
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