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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:


Q. I’ve had my eye on Hunter Boots for almost 2 years now. Each year, I feel like it won’t be in style the following year and that I shouldn’t invest so much in Rain Boots (since I live in Sunny Southern California). After 2 years, I still want them. I wanted to know if it would be a good investment for my boot collection. If so, any recommendation on color and what type of outfits to pair it with?

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A. Even in sunny southern California, you still need to be prepared for the occasional rainstorm - and there’s nothing that’s more practical and stylish than Hunter boots (or Wellie-style rain boots). Wellies are the rare combination of classic and trendy style. The key to finding a pair that you won’t tire of is to choose a simple color, rather than some of the flamboyant prints that come in and out of style. Believe me, you’ll wear your rubber boots for years and years. The color you choose depends on your personal style, but here are some options with staying power from Hunter and other brands:


As for what to wear them with, they pair easily with skinny jeans and leggings. But we also love them with shorts, dresses and skirts - perfect for sunny California! Here are some more ideas on what to wear with your rain boots.

Q. I just bought a pair of leopard print shoes, and I need help! Other than a white shirt and black pants, what do I wear them with?

A. Leopard flats are a serious favorite of mine, so you’re asking the right girl! Over the years, I have collected no less than 6 variations of the leopard flat. I wear them with literally everything. They do look good with black and white as you mentioned, but they also look great with denim, red, camel, olive green, purple, orange, jewel tones… in fact, I can’t think of many colors a leopard print doesn’t go with.

This season, I’m particularly loving leopard prints paired with military-inspired pieces like cargo pants in khaki or olive green. I also love them worn with a ladylike camel coat or camel sweater and a pair of dark jeans.

The bottom line? Don’t feel boxed in to wearing your leopard with just black and white, they work with just about any color in your fall wardrobe!

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Q. I have a problem finding knee high boots because my feet are disproportionate to my body. Although I stand at 5’9, my feet are a size 7. This means that any knee high boots I try on are too small to zip around my calves. The other issue is that I’m only 24 and most of the wide calf boots I’ve found are matronly. Are there any boots out there offered in wide calf sizes that are also fit for a 24 year old?

A. There’s no need to sacrifice style when searching for a wide calf boot. Here are several different styles that we’re loving this season, all with a generous calf width:


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