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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

Q. I am almost 6’ tall with an athletic/hourglass figure. I can range in size from an 8-14 depending on the season. At an 8, I’m about as lean as I can get and at 14 I’m enjoying extra goodies and drinks, but still not “overweight” by any means. I know it’s not a good habit, especially for my closet.

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I am a 12-14 right now. I have a pair of dark skinny jeans that fit really well and an awesome pair of on-trend knee high, flat brown boots. Are these ok for me? I feel like I should wear something to cover my larger parts (hips/outer thigh), but am having a hard time finding the right look. I’ve searched for long tunics and sweaters, but am just not sure what to wear with my skinnys/boots…or if I should skip them until I am smaller again?

A. Yes, yes, yes! You are tall, found a pair of dark skinny jeans that look great on you and have amazing knee high flat boots - what more can a girl ask for? Whether you are a size 6 or a size 16, your tall frame is made for this look! Your instincts are correct to look for sweaters, blazers and tunics to help conceal your bulges and give you a lean silhouette. Here are some options for you:

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. Are cargo pants in or over for the fall? If they are passe, is there something that has replaced them?

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A. You will be thrilled to know that the military trend is marching right into fall, and that includes cargo pants. Whether you bought a pair of skinny cargo pants or a silky relaxed pair this summer, or are interested in investing in a few new pairs for fall, there are several ways to wear them this season.

Try pairing skinny cargo pants with a draped tank or t-shirt and a strong blazer. Finish the look with ankle booties or a platform pump. If you prefer a looser fitting cargo, look for one in a slinky knit or silky fabric which gives them a dressier appearance. Pair it with a slim fitting top and a this season’s must-have desert boot or lace-up bootie for a modern military look for fall.

Here are a few images for inspiration (click on each image to shop the look):

Q. I am in love with the socks and heels trend, but I just don’t know if I can pull it off! I don’t want to look like someone wearing socks and sandals (a definite fashion faux pas), but most of the women I’ve seen sporting the trend have looked fabulous! What do you think? Is it worth trying and how do you suggest going about it?

A. We’re loving this trend this season also (check out this recent post in StyleBakeryTeen), but it can be a bit tricky to pull off. Keep in mind that wearing socks will visually cut off your legs, so if you’re not willing to lose a few inches of leg height, this trend may not be for you. Here are a few tips for successfully wearing socks with heels:

  • Choose thin socks made with a nylon blend. Cotton socks tend to be too thick and can stretch out or sag.
  • Make sure the top of the socks hit at a slim part of your ankle or calf for the most flattering look.
  • The easiest way to wear the look is to match your sock color to your shoe color.
  • Your skirt or dress hem should be short - mid thigh or higher.

A good pair of socks is a fairly inexpensive investment, so this is an easy way to experiment with your fall look. Have fun with it!

Here is some styling inspiration from a recent J Crew catalog:

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Some celebrity inspiration courtesy of Rihanna and Leighton Meester:

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photos courtesy of style.com and instyle.com

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