Fall Shoes: Looking Smart, Feeling Good

Sacrificing fashion for comfort is such a drag. We’ve rounded up some great shoes for fall and winter that will take care of your feet as well as your stylish eye.


Jeffrey Campbell Kayla-Fox Flat
There’s still time to flit around in some fab flats before the snows come. This houndstooth/patent leather combo is trés chic for the city or suburbs. $104, Lori’s Shoes

Söfft Ferre Mary Jane
Fall for the red patent on these oxfordized Mary Janes with padded footbeds. Also comes in black and pewter. $109.95, Nordstrom

Stuart Weitzman Lille Pump
When it comes to luxury shoes, look to Stu for heels that you can dance in all night. These may look perilous, but the high platform and excellent construction make this pump surprisingly comfortable. And the gunmetal python print? Swoon. $375, Stuart Weitzman

These Boots Are Made for Walking

Report Monroe Mid-Calf Boot
We’re seeing a lot of fold-over boots this fall, and the buckles on this comfortable heel add an extra bit of tough-girl chic. $139.96, Endless

Vince Camuto Piv Mule
Mules and clogs have made a comeback and are good options if you’re looking for height, thanks to their thicker heels and soles. $125, Dillard’s

Merrell Tetra Launch Boot
In addition to Merrell’s typical comfort and quality, these waterproof leather boots feature elegant snap tab details. Also comes in brown. $150, REI

Cole Haan Air Georgina Boot
A divine caramel hue meets a heavenly fit, thanks to Nike Air’s technology. $349.90, Nordstrom

When the Weather Outside Is Frightful

Nala Nefertiti Boot
Cozy up in this shearling-trimmed utilitarian lace-up with biodegradable foam cushioning. Also comes in black and chestnut. $284.95, Nordstrom

UGG Belcloud Rain Boot
Yep, they’re Uggs. Waterproof leather, shearling lining and rubber duck boot soles make for great puddle splashing. $225, Bloomingdale’s

Chooka Herringbone Wellington
Upgrade your regular old wellies to some that have a unique print, like this boot’s wool herringbone upper. $70, Piperlime

Hunter Welly Socks
Many rainboots (like the ones above) aren’t insulated for the truly nasty snow and sleet that we Chicagoans know so well. No worries, though—just nab some fleece inserts. These fold over the top of your boot and come in several colors and styles. $40, The Bootery

Don’t forget that insoles like Dr. Scholl’s or Insolias can cure many comfort ails. What are your tips for the most stylish comfy shoes? Leave your ideas in the comments!