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Q. What is your take on Ugg boots? I have been anti Ugg boots for years, but suddenly I am having a change of heart. I see them everywhere now, and they are growing on me, especially the cute sweater styles. And a few weeks ago, I had a miserable experience involving frozen toes and uncomfortably stiff flat leather boots that has pretty much convinced me that I need a pair of Uggs. But please tell me, honestly, is there any way to wear them without looking completely tragic? That’s a lot of money to spend to look really stupid, even if your toes are warm and happy!

ugg31229.jpgA. This is a question I can really relate to. For years, I was a die hard Ugg hater - I hated that they were so trendy, I hated that people wore them in the summer with shorts, and I hated the way they looked. Over the years, though, Ugg Australia has introduced a variety of styles to add to their classic line, which have a lot more style than traditional Uggs (in my opinion).

Coincidentally, I was given my first pair of Ugg boots just last month - this year’s hot Bailey Button boot. I’m not sure if it’s the arctic temperatures we’re having this winter or the updated look, but I am officially a convert and proudly wear my super warm, supremely comfortable and somewhat cute Uggs everywhere. A little late to the game, perhaps, but like you, they are growing on me. And considering that you can buy them everywhere from Bergdorf Goodman to ShopBop.com, they are most definitely not disappearing from fashion’s radar anytime soon.

Our advice? Choose a pair that has interesting details, like buttons, buckles or laces, and wear them with skinny jeans or leggings and a cozy sweater. Skip the knit styles which tend to look dirty after a few wearings. And please, do not wear them with shorts!

Q. I have a wedding in Atlanta this month. It is an evening wedding and I bought a great green dress for the occasion that would be accompanied by a black sparkly shawl. I was wondering if it was acceptable to pair that with a great pair of black calf boots with 3 inch heels and a buckle? I thought it looked pretty good, but have been told not to wear boots to a wedding. Is this true?

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A. Your dress and shawl sound lovely. Unfortunately, however, I agree with your friends that boots are not the best option for an evening wedding. Most boots would be considered too casual to wear to a formal affair. You are much better off opting for a black evening shoe. Here are a few of our favorites:

Q. I’ve been eyeing the Tuxxedo shoes from Steve Madden for a while now. I absolutely adore them in black and white, but I wonder if they’re too formal looking for every day wear? How I could I rock them or the ones in cognac?

A. Menswear-inspired Oxford shoes can be worn casually many different ways. Take a cue from Selma Blair, Taylor Swift and Sienna Miller by pairing your Oxfords with everything from dresses and skirts to skinny or boyfriend jeans.

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The black and white Tuxxedo does have a slightly more dressy feel, but you can still wear it casually - and it would look great with a boyfriend blazer and leggings. If you’re unsure about whether you can pull it off or not, then go for the cognac color like the pair Taylor Swift is wearing above.

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Q. I work in a business casual atmosphere where there is a lot of flexibility in appearance. I’m always annoyed with my shoes by the end of the day, even my flats. Are there fancy sneakers that I can wear to work with trousers or something equally comfortable?

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A. Your appearance matters, even in a business casual office, so it’s always important to look neat and professional. Therefore, we are not fans of sneakers with trousers. If your usual shoes or flats are uncomfortable by the end of the day, you can try some of the many gel insoles available, like these from Dr. Scholl’s.

If the insoles don’t work, we recommend investing in a pair of Cole Haan shoes with Nike Air technology. They offer a huge range of stylish shoes that contain low profile cushioning. In other words, they look like a shoe but feel like a sneaker.

Q. What is the best way to wear booties?

A. Not only are ankle boots a huge trend, but they’re also extremely versatile. You can wear them with jeans or leggings or in place of a pump with dresses and skirts. Since booties range from super low (sometimes called shooties) to heights that are well above your ankle bone, how you wear your boots depends on the style of boot.

Shooties or shoe booties look best with skirts, dresses and long skinny jeans or leggings. These are the most flattering style to wear since they come down low on the leg, making them look longer than with other styles of boots. Booties that come up a bit higher on the ankle can also be worn with skirts and dresses but look best on women with slim calves. Another option for ankle boots is to wear them with skinny or boot cut jeans or leggings. Here are some celebrity photos for inspiration:


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Katy Perry, Reese Witherspoon, Kristen Stewart and Rihanna all wear booties with bare legs and dresses or skirts, though tights would also be a great addition to any of these looks. Note that all of the hemlines hit well above the knee for a flattering leg look.


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Rihanna, Nicky Hilton and Leighton Meester wear booties of various heights with skinny jeans and leggings, while Keri Russell shows how to wear them with boyfriend jeans.

photos via InStyle.com

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