The end of the year quickly approaches and with it, another fashion dilemma: what to wear on New Year’s Eve. But regardless of where you’re headed to celebrate the end of 2011, I’ve come up with a few different options for your night out.

Option #1: Black tie event

Whether you’re headed to the Statler City Ice Ball or a more intimate gala, you’ll need the perfect dress for such a fancy event. New Year’s is the perfect time to wear the most sparkly thing you can find, so why not choose a shimmering gold floor-length gown and matching gold heels? Or, if you’re not in the mood for that much sparkle, choose a dress that has a little something special — and don’t forget some killer accessories.

Option #2: Dressed-up dinner

Though you should keep it pretty conservative for dinner (especially dinner with in-laws), you can still have fun — it is New Year’s Eve, after all. Try a flattering but demure shape, like a high-necked belted dress, but in gold chain mail. Paired with black tights and black ankle boots, you’ll be fully covered yet festive. Or, opt for separates instead, like a black feathered skirt, a sequined top and patterned tights. Get a little wild — conservative doesn’t necessarily mean boring.

Option #3: New Year’s bar-hopping

There are so many fun options for a night out at a club or bar that it’s hard to choose just a few. You can definitely show a little more skin than you otherwise would, but make sure it’s tasteful: if you’re going to wear a short skirt, wear a shirt that will keep you covered. If you prefer a thin tank top, pair it with jeans or pants instead of a micro mini. After all, you need to leave SOMETHING to the imagination. But don’t be afraid to wear something festive and fun — it is New Year’s, after all.

Now that you’ve found the perfect outfit, you have one problem left to solve: shoes.

Dear Avery,
I want to wear really hot shoes for New Year’s Eve, but those high-heeled suckers hurt my feet like it’s nobody’s business. I’d prefer not to wear flats—they tend to make me look like a tree stump. Any suggestions on comfortable heels that are also fashionable? Also, I don’t want to look like a street-walker, FYI. I’m wearing a basic black above-the-knee dress, and I’m open to color and style suggestions for shoes.
Thanks,
Dogs are barkin’ in Buffalo.

The term “comfortable heels” sounds like an oxymoron, but believe it or not, bearable heels aren’t a mythical creature. Oftentimes, finding a comfortable heel is hit-or-miss — a cheap shoe from a store like Forever 21 may prove more comfortable than a $200 pair from Lord and Taylor.

While a thin stiletto will probably have you in tears by the end of the night — the ultra-thin heel doesn’t provide much support — a shoe with a thicker heel and a platform while likely be more comfortable. This shoe made by BCBG and available at Lord and Taylor has a thick five inch heel, but the platform makes you feel closer to the ground, as well as providing support. And the fact that they’re covered in tiny studs gives them my seal of approval.

Another option is the ankle bootie. While these often have a thinner heel, the fact that they come up to your ankle might help take some of the pressure off the rest of your foot. Plus, if you have weak ankles, they will definitely provide a little bit more support — no one wants to end up with a sprain on New Year’s. This pair from Steve Madden is a good bet, if only because it comes in a cool metallic distressed leather. While not all ankle booties are going to be comfortable, they’re generally a safe choice — I got a pair from Payless six years ago and they’re the most comfortable heels I own.

If you’re not a fan of any of my other suggestions, you might opt for wedges instead. I hesitate to suggest wedges because, although they’re often super comfortable, I only really like wedge sandals in the summer. Winter wedges can often be, for lack of a better word, hideous, and I don’t want to promote anyone wearing ugly shoes, especially on New Year’s Eve. While this pair from Baker’s might break your rule of not looking like a street walker, they’re pretty cool if you’re looking to get a little crazy.

Feature photo courtesy of Flickr / Rick Chung