When COVID hit, spring was right around the corner. It was warmer days ahead and it was easy to dress for it during the lockdown. Throw on a pair of sandals or flip flops and you were done. Now we’re heading into fall, still dealing with COVID and anxiously anticipating a spike in cases. Fingers crossed the active cases will continue to decline but even if they do, we’re still going to be living very differently than we have in years past. Once it gets cold outside, do you have the right shoes for this casual life you will be living in?


When it came to clothing, many of us were caught off guard when the world went home to weather the COVID storm. Dressy clothing became unnecessary and women found themselves without enough mid-casual clothing to get them through it. Now we’re in a new season and likely in the same predicament. If you are without casual shoes for fall that will keep your feet warm, I have put together looks using comfortable, casual booties for fall and have a bunch more for you to shop for at the end of this post.

Outfit #1


When Dankso expands beyond their utilitarian clogs, they actually do some pretty cool styles. These booties are a great example. I see so many women in my neighborhood in a pair of Dansko booties for their great walkability. I styled the booties with a pair of skinny jeans from Kut from the Kloth, a black v-neck sweater from Equipment, a bag from Frame, and a statement necklace from Anthropologie.

Outfit #2


If you like Uggs but don’t like the clompy style, they have released this pair with a hidden wedge. I styled these booties with camouflage leggings from J. Crew and an oversized hoodie sweatshirt from COS and a functional crossbody from Tumi.

Outfit #3


Dansko isn’t all clogs all the time and I like their take on other styles that center around comfort. This pair has a cute little wedge and pairs well with jeans and dresses. I styled these booties with a t-shirt dress from Everlane, a denim jacket, a printed scarf from Nordstrom, a cognac bag from Longchamp, and rosewood drop earrings.

Outfit #4


A simple pair of chelsea boots are easy, comfortable, and perfect for casual, especially when they are from a comfort brand like this pair from Kork-Ease. I styled this pair with raw edge straight leg jeans from Rag & Bone, an olive crewneck sweater from J. Crew, and a blush tweed blazer from Boden. I finished the look with rose gold drop earrings and a burgundy bag from Talbots.

Outfit #5


An alternative to booties for fall is a pair of high top sneakers, like this chelsea style from Rothy’s or a hidden wedge style. They can offer more coverage than a traditional pair of sneakers while offering comfort. My sister has this pair and says they are incredibly comfortable. I styled them with a pair of pleated joggers from Frank & Eileen, a loungey grey sweater from Free People, a grey canvas tote from Herschel Supply Co., and door knocker earrings from Kendra Scott.

Shop for Comfortable, Casual Booties