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Winter Pears: How to Transition From Shorts to Snow

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Love, Frank has returned as a weekly style advice column tackling your hard-hitting fashion issues and addressing a different fashion glitch each week. Submit a query here.

Image via (plus more tips from) Style Guru.

Dear Frank,

I'm pear shaped. This works out great for me in the summer, because I can do a fitted shorts/baggy top combo and look like I'm relatively the same size all over. This is a lot harder in the winter, though, because the same baggy tops look frumpy without a lot of leg. Any tips for how to flatter this unfortunately shaped piece of fruit?

Ripe for a Change

Howdy Ripe,

I'm surprised your go-to summer ensemble involves a baggy top—generally stylists, personal shoppers, and the clothes-minded would suggest something a little more tailored on top. They might even show you something that's sleeveless or embellished in some way.

Generally, a pear-shaped lady has hips and a tush that are wider than her shoulders. Further, a pear's bust will be on the smaller side—otherwise she'd be Joan from Mad Men, an hourglass.

Hence the tailored, embellished top—which draws the eye upward.

Image via (plus more tips from) Style Revival.

My suggestion would be to forget what you know for an outfit or two and see how you look and feel. Swap out the fitted shorts for a roughly knee-length A-line or pencil skirt or a well-tailored pant that skims the hips but ends with a generous, wider hem. Replace the baggy top with something a little more fitted—like a button-front blouse.

If you really feel unbalanced, look for a wider sleeve, a boat-neck, or even something with an empire waist. You should also feel free to layer up the top half—we're looking for balance and something that draws the eye. So add a blazer that fastens under the bust; or a trim cardigan; a waist-cinching belt; a some statement jewelry.

Stick with dark-colored bottoms with a bit of stretch. You should avoid bottoms with a lot of crap going on—cargo pockets, unsubtle prints, wacky embroideries. Save those embellishments and prints for your top half. And choose shoes with a heel and a bit of a point at the toe. A round-toed shoe will make legs appear stubby rather than elongated. Also note that bias-cut items—or garments sewn from fabric that is cut diagonally—will have an elegant drape and substantially more stretch. It's a technique that curvier women look for: Extremely flattering and beautifully flowing.

I guess this isn't too much a departure from your summer look—lengthen those fitted shorts to a sleek, wide-hemmed trouser; and cinch that top a bit. You'll be good to go.

And, I say this all the time, find a tailor you like and trust. And go to him often. Search Yelp, ask friends—but a tailor can add or remove a dart, or taper a leg, or hem a cuff in no time for a negligible amount of money. Little tweaks like that can make a garment that feels a little frumpy look elegant and made just for you.

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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