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Q. I love my ballet flats but as real winter approaches, I want a little more covering my toes — but I don’t want to lose the polish that ballet flats offer (or their lightness & ease). I am seeing a lot of tall boots or biker boots, but I am not a biker chick — I am a prep! Help!

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A. We, too, love our ballet flats. But at some point when the temperatures drop low enough, we are forced to give them up for something a bit more practical. As a replacement, I am assuming that you’re looking for flat shoes that suit your preppy style. Since you mention tall boots or biker boots as an option, perhaps you are not limited only to shoes and will consider a boot as well. A classic riding boot always looks polished and it’s a very comfortable option. Flat booties, desert shoes and menswear-inspired brogues are also chic alternatives to the ballet flat.

Below are some polished, comfortable and easy shoes to consider that will keep your toes warm:

Q. I want to wear this super cute dress to two different holiday parties. One is for hubby’s work/client party (read: conservative, stuffy lawyers) and the other is a more casual gathering with friends. I live in Florida so I don’t need to be in heavy layers, but tights and a little something to cover my shoulders would be perfect. Can’t wait to see what you come up with, because this one has me stumped!!

A. You picked a great dress with many possibilities. For your husband’s work party, I suggest slipping a blazer or tuxedo jacket over the dress, adding a pair of black tights and heels. A great necklace and clutch will finish the look. For a gathering with friends, I recommend adding a lightweight leather jacket or a sequin trimmed cardigan, each paired with a chic pair of booties, no tights. Or, you could always wear the dress alone paired with booties and an edgy necklace for your casual get-together.

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Q. I love wearing denim skirts but hate how the front zipper has a tendency to add bulk and stick out in exactly the area I don’t want any extra fullness. Do you have any suggestions for a short denim skirt with a flat front or another trick to keep my tummy from looking larger in my beloved denim mini looks?

A. I know exactly what you mean, and it can be very frustrating. Your best bet is to seek out a style that does not have a traditional zip-front fly, perhaps one with buttons down the front or an asymmetrical seam, or even a stretch pull-on style. Below are a few atypical options that should solve the issue for you while still giving you the casual cool look of a denim skirt.

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Q. I’m not sure how to wear my sleeveless sweater dresses. I want to wear them in the wintertime. Do I wear something over them? Under them?

A. Sleeveless sweaters and dresses are great layering pieces for the winter. It’s always best to wear your chunkiest layers on top, so if your sweater dress is somewhat thick, then wear it over a thin jersey turtleneck or long sleeve top and pair it with tights and boots or leggings and booties. If your sweater dress is thin, you might be able to layer a jacket or even a knit cardigan on top.

Q. I’ve got several holiday parties coming up, so I’m ready to splurge on a great dress! My legs are my best feature, can you recommend some great options for me?

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A. You’re in luck! Leg-baring dresses are a huge trend for holiday - and if you’ve got ‘em, flaunt ‘em! Here are some sexy, shimmering, festive dresses to wear all season long:


Need something to wear with your dress? Check out our favorite sparkling jewelry, festive evening shoes and glam evening bags.

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