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Q. I’m looking for a stylish, yet warm and cozy boot to wear this winter. I love how soft and comfortable UGGs are, but I just cannot bear how unattractive they are. Can you offer some more fashionable alternatives that are just as comfy?

A. There’s a reason the admittedly not-so-cute UGG boots have stuck around for so many years - they really are incredibly soft, warm and comfortable. However, they’re not the only cozy game in town. Here are some chic alternatives to the ubiquitous UGG shearling boot:

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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 am 5’1” and curvy, can I wear ankle boots or booties?

A. If you choose the right style bootie, you can absolutely incorporate this seemingly-everywhere trend. The key is to look for short styles that dip down in the front, allowing more of your leg to show. Wear these with skinny jeans, leggings or opaque tights in a similar color to the boot and you’ll be able to wear booties in the most flattering way for your petite curvy figure. Avoid styles that come up beyond the ankle bone as these will only make your legs look shorter and calves look wider.

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Here are some great options for you:

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Q. With the cooler weather quickly approaching, I am on the hunt for shoes I can wear during my winter commute. I typically walk about 30 blocks to/from work and need some comfy shoes that keep my feet warm. Unfortunately the shoes I have found so far may be supportive and warm, but they are not cute, or the shoes are cute, but have no support whatsoever. Are there any particular brands or shoe styles I need to look into? I would love your advice!

A. One of this season’s hottest trends also happens to be super comfortable and cozy for winter: shearling and faux fur lined boots. Available in a range of heights and price ranges, the waterproof version of this boot will not only keep your feet dry, but also warm.

Since the shoes you wear to brave the weather and walk 30 blocks might not be the same ones you want to wear all day at the office, we suggest carrying a pair of heels in your work tote to change into (or leaving a pair at work). The boots will also ensure that your pants or tights remain dry.

Below is a selection of warm, comfortable shoes in shearling and non-shearling styles that will be perfect for your winter trek to work:

Q. I bought an amazing pair of brown lace-up (granny style) boots. I have no clue what to wear with them besides pants. The weather is turner colder and I want to show them off!

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A. You’re right to want to show off your lace-up boots this season! Your options for what to wear them with are numerous, including dresses, skirts, skinny jeans and leggings. Wear them with anything you would wear with a tall boot or riding boot. Here are two looks for inspiration:


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