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Q. Once again I revisit an issue I deal with every winter. After enjoying sixty or so pairs of sandals in the warmer months, I find myself limited with just a couple of pairs of shoes during the winter. I am not talking about special occasions, just the everyday, work, running around, comfortable but good looking (heeled) shoes. Even though I live in a somewhat mild climate, we still face many days of cold and rain and need to keep our toes warm. When it’s miserable outside and I put on yet another pair of black or dark pants, the natural choice is black shoes. As I find most closed toe shoes uncomfortable (too narrow, toe box too low) and comfort shoes are flat and frumpy I am thinking of another solution. Since peep toes of every style are so abundant right now, how about wearing them with tights of the same color?

I love shoes, but find winter so uninspiring. Would you please offer some solutions as well as more color options for the lower half that are more exciting than black?

A. You’re in luck, this season brings with it some fun and exciting new shoe trends, as well as some great neutral alternatives to black. Here are some of our favorite trends to liven up your fall/winter shoe wardrobe:

Peep-toe ankle boots - The perfect answer to changeable temperatures is the peep-toe ankle boot. Wear it with everything from skinny jeans to a dress. When the temperature is chilly, opt for tights or hosiery in a similar hue to your boots.

Suede desert boots - My personal favorite of the new fall trends, the updated version of the classic desert boot comes complete with chunky heels, comfortable wedges and even platforms. Opt for an earthy color like olive green, smokey gray or neutral camel as the perfect alternative to your usual black. The best part about this shoe is its versatility: it looks great with bare legs and a dress or skirt, tights and a dress or skirt, and of course pants and jeans.

Biker boots - A low heeled motorcycle-inspired boot is the ultimate in comfort (no concern for narrow toe box here). Try them with leggings, skinny jeans, a dress or a skirt. Black, brown and even gray are the colors of choice.

Flats - Whether rounded or pointy toe, girly flats continue as a foot friendly, yet stylish, option. Try an animal print or rich fall color as an alternative to black to liven up your dark pants.

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

Q. I’ve recently been on the hunt for knee high suede grey boots but wasn’t sure what I can pair them with. Any suggestions?

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A. We’re loving gray suede boots this season, they’re the perfect neutral to wear with black, olive, denim and fall’s requisite jewel tones like red and purple. Knee high boots are best worn with dresses and skirts that hit above the knee, skinny jeans and leggings. Gray suede boots are the perfect investment to wear all fall and winter long - and again next year. Here are some styles to consider:

Q. I am wearing this dress to a (not super fancy) evening wedding in Connecticut this summer and also to a lower key wedding in Crete this fall. I’m looking for styling help - accessories, purse, layer, shoes? I do have a pair of neutral metallic peep toes that may work for the CT wedding. If you could help at all so I can get more out of this dress I would appreciate it! I’d love ideas for fun jewelry - and whether to wear simply earrings or earrings and necklace? I feel that there’s a lot of pattern in the dress.

A. You can do so much with this bold printed chiffon dress, it’s a great choice for not-too-dressy weddings - and one that you will get a lot of wear out of in the future. If the temperatures are warm, we suggest wearing it on its own with metallic strappy heels or your peep toes. You might want to bring along an evening wrap in case you get chilly. For jewelry, we recommend you skip the necklace and opt for dramatic drop earrings that incorporate one of the many colors in the dress. You can also add a pretty bracelet or cocktail ring. An evening clutch finishes the look.

For a more sophisticated look, try layering a tuxedo jacket or dressy black blazer over the dress and opting for black heels. You can also have fun dressing it down for a dinner out with friends with a denim jacket, leather jacket or boyfriend blazer and a pair of booties or wedge sandals.

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Q. Joie makes some boots for fall that I love love love, but I can’t justify the price unless I can think of a bunch of ways to wear them. Can you recommend a couple of different ways to style these? Is it possible to wear them in a business casual office?

A. Lace-up boots, both tall and short, are a huge trend for fall. We’re loving them with everything from dresses and skirts to skinny jeans and leggings. You can certainly wear them to your business casual office with anything you would typically wear with a tall boot.

The military-inspired Joie Refugee boots you love are a bit of an investment at $535, but they’re sure to be your go-to boot this fall and winter if you do take the plunge. The great news is, there are many similar boots available for a lot less money if you like the look but aren’t too attached to the brand name. Check out these more affordable alternatives:

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