Looking for Cute, Comfortable Heels for the Holidays? Well, You’ve Come to the Right Place


True, we love flats at Glamour, but, true also, sometimes you just want to wear a pair of heels. Jumping from festive lunches to holiday parties, friendsgivings to family dinners, the winter season is chock-full of celebratory occasions.

There’s just one problem: Between the cold weather and hours spent dancing the night away, our best sky-high stilettos don’t quite do the trick. You don’t have to wear a pair of kitten heels to feel totally comfortable in your kicks this season, though. There are plenty of chic options that stand up among the likes of your highest heels. Follow our tips below and we will have you partying the whole evening long.

  1. As a most basic rule, look for heels slightly shorter than you typically wear.
  2. If you still crave the elevation you’re used to, slip into a pair of pumps with a built-in platform to cheat the actual heel height.
  3. The chunkier the heel, the more comfortable the shoe. You won’t have to worry about balancing on a pin and can disperse your weight more equally on the ball of your foot as well as your heel for happier toes.
  4. Strap yourself in with an ankle-tie or oxford pump. Giving your foot more stability on stilts is key to a pain-free evening.

Though these tips are not mutually exclusive, you don’t have to look for a shoe that fits all the above parameters at the same time for your toes to thank you. Pick and choose your most important and keep them in mind when shopping for your next pair of dancing heels. We’re even getting you started with the 25 styles below!

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