How to Make Menswear-Inspired Dressing Work

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Love, Frank has returned as a weekly style advice column. Addressing a different reader's fashion glitch each week, he tackles all the hard-hitting issues—like whether you can wear white to a wedding and where to find cute shoelaces.

Dear Frank,

I really like the look of menswear (oxford shoes, vests, ties, tweed, blazers, briefcases, etc), but when it actually comes to wearing mens' clothing, no matter what size, the fit is very awkward on me. Do you have any advice on how a women can dress in menswear?

Love,
Modern-Day Mulan

Dear Mulan,

I love a menswear-inspired womenswear look—but you're right, it can be tricky. It can get costume-y or silly or simply unflattering. And those issues often relate to fit. Actual men's clothing isn't going to work for you; and the menswear-inspired womenswear probably won't fit just anyone off the rack.

Menswear is tailoring. Men don't wear frocks—they wear tailored garments. And the men who generally look best in their clothes are the men who get their tailored clothes tailored to a perfect fit. A man without a decent tailor is, well, probably the type of man you see at the Olive Garden wearing mesh basketball shorts.

So that's step one—you need a tailor or a seamstress (who can also tailor). One you can trust to do what you ask and not what they think is correct (because many tailors still think Working Girl and Wall Street are what's correct and they won't give it up). And you need to, you know, go see them; and be willing to invest a little money in alterations. But! They can get your shrunken Oxford shirts and waistcoats and little glen plaid blazers looking like they were made for you; and not just like you're wearing something from dad's closet.

As for accessories—just pay attention to proportion. Don't be afraid to wear a tie. You can buy one from the men's store, but stick with the skinnies. Brands like Original Penguin, Ben Sherman, and French Connection sell slim neckwear at department stores like Macy's for a relative bargain. J.Crew has a variety of tie widths, and none are overly wide. At the end of the day, it should look like you're wearing the tie and it isn't wearing you.

Briefcases and satchels, same thing. Look for those traditional menswear silhouettes, just 20% smaller. I love a girl in a Jack Spade bag—and they make all kinds of sizes. Those Cambridge Satchel Company bags come in a couple of sizes (and approximately 2 million colors), too.

Beyond that, I would just caution against going too far with the menswear-as-womenswear look. Do get a great girl-sized Rachel Comey wingtip. Do flirt with traditional menswear patterns—tartans, houndstooths, tweeds. Do keep a couple of great (tailored) blazers in your arsenal that aren't just for job interviews. Do get to know your tailor and the joys of a successfully tapered pant or beautifully adjusted shoulder. Do shop Madewell and Ralph Lauren. But maybe, you know, don't go full-on "Express Yourself" Madonna because that's probably crossing the line.

And despite what Warby Parker might say, no one needs a monocle.

Got a style question for Frank? Leave it in the comments or email one in here. Then buckle your two-toned leather Moschino belts, folks, because it's going to be ? Something.
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