Shoes That Are Comfortable AND Stylish

As of late, I’ve had multiple clients searching for fall shoes and boots. And while these women care about style, fashion, and how they look (I mean, obviously, they hired a stylist). They also equally care about comfort. Done are the days of shoes that feel like knives in your feet. Or backaches from wearing too high a heel or a shoe with minimal support.

However, these clients do not want to settle for orthopedic-looking shoes or defaulting to running shoes with every outfit. And while it might seem that comfort and looks can’t co-exist in the footwear category – I’m here to let you know they can and they do! I’ve searched high and low to find the best looking fall comfort shoes and boots for you!

And surprise, I found a lot! From tried and true comfort brands that have (finally) married comfort technology with fashion sense. And from brands that I’ve personally tried or had a client try so I have direct feedback. Now, that all being said, footwear comfort is VERY personal. One person’s most comfortable pair can feel torturous to another person. So consider this your guide – they all have my stamp of approval in the looks department – and sometimes you’ve got to try on quite a few pairs to find the one that fits.

Fall Comfort Shoes:

Chelsea Boots

Chelsea boots are a wonderful silhouette that is eternally classic. In fact, I’ve had a pair for 15+ years that I’ve worn consistently for that time and they’ve never gone out of style. A Chelsea boot typically is a slip-on boot style and has an elastic side panel that allows them to slip on and off with ease. This season, a Chelsea boot with a chunkier heel is what makes it feel more current.

Combat Boots

Combat boots are cool. They can also be ageless and feminine if you find the right pair. I wear my pair (linked below) almost every (non-summer) trip to a city (NYC, Florence, Paris, London, Chicago) because I can walk comfortably all day, and they still look polished for an evening out. P.S., they also look great with dresses.

Oxfords + Loafers

Oxfords and Loafers are perfect transitional shoes. And they work in the colder months as well, just add a sock. I like the sock to either match the shoe color OR the pant color. And if you like your outfits on the spicy side, don’t match your sock and pick a fun pattern.

Tall Boots

IMHO, having a tall boot in your wardrobe is essential. It might not be worn all the time but it’s there when you need it. Especially to wear with skirts or dresses when it’s cold. I generally recommend a boot that is tighter in the shaft and without a lot of hardware, so it creates a leaner leg line.

Sock Boots

Oh man, I’ve been writing about sock booties for almost 7 years I think. Basically, if you’re having a hard time wearing non-skinny jeans because you don’t have the right shoe, this is likely what you’re missing. Tight in the shaft and on the higher side. They’re worn UNDER your straight leg or crop flares and look fantastic.

Heels/Flats

A Few Notes About Fall Comfort Shoes and Boots

I realize that most of the shoes and boots I’ve linked are on the pricier side. That is partly because to get a good quality, comfort shoe, requires extra craftsmanship and technology to create the support and shoe feel. If you have foot or back issues, footwear is not the area of your wardrobe to cut corners. It’s actually the time to invest. As one wise client said to me “when my shoes are uncomfortable and my feet hurt, it ruins my whole day” Amen, sista!

You might also notice that many of the shoes and boots I linked are basic colors, such as black or brown. Overall, comfort shoes might be nice looking but they’re likely not the most stunning pair you’ve ever seen. So allowing them to blend in rather than stand out is a good rule of thumb. Some, of course, are outfit heroes (like the animal print loafers) but mostly they’re part of the supporting cast.