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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 am in search of a sequin mini dress with 3/4 quarter or long sleeves to wear to a wedding in NYC in February. This dress seems to be impossible to find for under $300. Can you help me find something cute and classy?

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A. We love a good sequin mini dress, especially with long sleeves or 3/4 length sleeves which help give a short dress a more sophisticated silhouette. We found some beautiful dresses in your price range below that are so pretty, you won’t want to wait until February to wear! You’ll get plenty of wear out of your dress for holiday parties or New Year’s Eve. You can also dress it down for a fun night on the town with a leather or denim jacket, or a blazer.

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:


Q. Cold weather is coming! For northern girls like me (Milwaukee!) the cold weather season presents a difficult challenge for me, as my favorite clothes to wear are flats with trousers, flats with skinny jeans, flats with anything! But I don’t like them with socks, and then my feet get cold! Can you provide some variation on the flats with pants look for winter? Do socks look ok with this style?

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A. I’m a big ballet flat person myself and wear them as long as possible into the cold weather without socks. When I finally can’t stand cold ankles any longer, I typically turn to ankle boots and tall boots. However, I have also been known to wear socks with flats on occasion.

Some flats are easier to pair with socks than others. For instance, an Oxford flat or menswear-inspired shoe looks great with a sock, and mary jane style flats tend to look great with tights. The trickiest kind of flat to wear with a sock is a ballet flat or similar shoe that shows off a lot of the top of your foot (instep), however, it can be done. The key to pulling off this look is to match your sock color to your shoe color. Black is always the easiest, so a black sock with a black shoe looks fine. Choose a smooth sock (or tights) that won’t bunch up.

There is a big trend towards socks this season, however, as designers sent many looks down the runways showing off socks with heels, sandals and ankle boots. Try experimenting with some fun socks with your flats in a “meant to be seen” fashion.

Your other alternative, of course, is to switch to a flat ankle boot or flat tall boot. You’ll get the same comfort you’re used to without worrying about socks and exposed ankles. Here are some styles to try:

photo via: lookbook.nu

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