Off The Cuff: I Need Some Cool, Comfy Shoes For My Walk To Work

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Dear Winona,

I recently moved to a neighborhood near my office and now I can walk to work! Any recommendations for comfortable shoes to wear on my new “commute” that are easy to stash once I get to work and put my heels on?


Walking Girl

Dear Walking Girl,

I grew up way out in the country, and lying in bed at night I used to gaze out my window and think, “Maybe someday I’ll live in a cool apartment in the city where I can walk to stuff.” That was literally my big dream of far-off adulthood. That I’d be able to walk to a coffee shop or an office or a movie theater. So I just had to take a moment to say congratulations, you are LIVING MY CHILDHOOD DREAM!

Finding the right shoes for this life dream scenario can be tricky, but it’s a fun challenge. Here are a few of my favorite options:

Cute sneakers.

I was in DC last week and saw many women on the Metro wearing sneakers for their commutes to and from work, and they looked SO COOL. Why? Because they chose badass sneakers that looked purposeful and complemented their work clothes. My favorite look (and one that seems to be very popular right now) is a simple pair of Nikes in classic black and white, like these. Slip them on with a pencil skirt or a pair of slacks and set a new speed-walking PR on the way to the office.    

Fold-up flats.

If your walk is relatively short and you don’t need a ton of support, foldable flats are a great option that are easy to swap out for work shoes once you get to the office. Most foldable flats are designed to be little more than house slippers you wear when your feet hurt at parties, so be sure to opt for a pair with a real sole for real walking. I’ve heard great things about Tieks: they’re foldable, high quality, and stylish enough to wear

Walkable work shoes.

The ideal footwear scenario here is a pair of shoes that you can wear on your walk to work AND at the office. My answer for comfortable, dressy shoes is always the same: wedges. They look great with pants or dresses and I’ve found them to be even more comfortable than flats over the course of a workday. This not-too-high wedge from Rockport is pretty perfect. This time of year, boots are another great option: look for a pair with a low heel, good arch support, and a style that’s streamlined enough for the office. Aerosoles have always served me well, and I love the classic style of these riding boots.

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