Chic, yet comfortable, winter shoes and boots for travel

Q. I’m headed to London for the Christmas week and will be doing tons of walking. Since I recently hurt my knee, comfortable shoes are really important, but I don’t want to look like a fashion victim in big clunky sneakers. Also I typically wear skinny jeans/pants so they look a bit weird paired with a sneaker, but it will be too cold to wear a maryjane type walking shoe. I’ve been desperately looking for comfy boots that I can sightsee in all day, bonus if they’re weather-proof for rainy London! I have extremely narrow calves so on top of that, so I have a problem finding tall boots that fit. Thank you!!

A. For walking around London with your skinny jeans, I would recommend investing in a chic pair of rubber soled ankle or mid-calf boots to avoid having to worry about fitting a tall boot to your narrow calves. Though comfort is a priority, that’s no reason to sacrifice style. As a personal favorite, I have walked for hours in my Frye Engineer boots, just add a comfy thick sock — and they look great with skinny jeans. And when it comes to comfort and warmth, you can’t beat an Ugg boot, though whether you think they’re stylish is up to you. Finally, I love the look of a rugged fur lined boot like the Sorels below with skinny jeans, even if your winter coat is a bit on the dressier side, it’s a great contrast (and very London!). Plus, I can personally attest to how amazingly comfortable they are.

Below are some options for you to try out for your trip. I purposely selected only boots from Zappos because of its free shipping and return policy. This will allow you to order several pairs of boots at once and wear them around the house as much as possible to select the one that will be most comfortable for a week’s worth of walking. Bonus, they’ll all serve you well for the damp British weather.


Back to Top