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


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. 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:

Q. I found this beautiful green dress to wear to my father’s wedding in July. It is a daytime wedding in New York City so the style is a sort of summertime chic. I am not sure what shoes fit with this dress. Black seems too nighttime and wedges seem too casual. Also most of the styles I find have ankle straps and I don’t want to cut off my already short legs. Any suggestions?


A. Your best bet is a barely-there strappy sandal in a light or metallic color. Here are some leg lengthening options that won’t break your budget:

Q. I have an animal print (cream and brown) mid calf length dress that i need shoes for. My legs are heavy in the calf area and I am relatively tall (5’7”). I am not overweight but certainly not skinny.

A. You’re best shoe option is a nude colored heel or wedge sandal, without ankle straps. These will help to lengthen and visually slim your leg, while pairing beautifully with a cream and brown animal print dress. You may also want to consider hemming your dress so it falls closer to your knee (either at, below or just above the knee) since a mid-calf length tends to make calves look larger.


Here are some nude shoe options for you:

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