Our Favorite Boots for Fall and How We’re Wearing Them

The shift from summer to fall creates an innate feeling of newness, doesn’t it? A clean slate. When we were younger, one of the biggest things to look forward to this time of year was, of course, back to school shopping. New clothes, new backpack, new school supplies, and always, always, a new pair of shoes. And that’s one autumnal pastime that I just can’t seem to part with.

Fall footwear is one of my favorite things to purchase. As Rose from the movie In her Shoes puts it, “shoes always fit.” And it’s true. No matter how many tacos or margaritas you may have indulged in this summer, shoes will always be that reliable online purchase you can make without worry that you’ll spiral down the path of recounting exactly how much Chipotle you’ve eaten for lunch these last few months. Because if you’re anything like me, that’s a road you definitely don’t want to go down.

This season, our team partnered with Sole Society, one of our go-to websites for fashionable, affordable footwear and accessories, to pick our very own “back to school” boots from their fall collection. Whether you’re on the hunt for work booties, a chic over-the-knee style, or something a little more casual, they’ve got pretty much every style you can hope for. (Bonus: they have clothing now too!) Today we’re showing you how we’re styling our favorite new boots for fall, and exactly how you can recreate the look.


Cofounder Alaina Kaczmarski’s Fall Uniform

SHOP THIS LOOK: Ponte Leggings ; Wide Brimmed Hat ; Devyn Booties


Favorite fall footwear and how you style it: Well I really love every and any kind of a boot, I’m really excited about these new suede booties! You get the elongating perks of a heel, but the chunky heel makes it super easy and comfortable to walk in. Plus they work with every outfit and can be dressed up or down.

Favorite fall Drink: a piping hot almond milk latte with a dash of cinnamon

Favorite movie to watch in autumn: Harry Potter – I love any movie where the cast is “going to school”

What you’re looking forward to most about the season: Fall has my favorite temperatures: those 50-60 degree days and evenings that allow for layers and sweaters! You can be outside and enjoy it comfortably, and you can be cozy at night. It’s the best.

Go-to fall comfort food: a homemade pot of chili with all the fixings!


Cofounder Danielle Moss’ Fall Uniform

SHOP THIS LOOK: Honor OTK boots; Mikayla Structured SatchelFaux Leather Jacket

Favorite fall footwear and how you style it: I love wearing OTK boots with jeans. As someone who wears denim almost every day, it’s always fun to mix up always wearing booties or loafers every day. These boots can be dresses up or down and make me feel a lot more fashiony (I know that’s not a word) than I am.

Favorite movie to watch in autumn: When Harry Met Sally

What you’re looking forward to most this season: I’m getting married in Paris the second week in October, so autumn in Paris!

Favorite nostalgic song: Holocene by Bon Iver always takes me back to crisp fall morning walks on the lake with my dog, Buddy.


Assistant Editor Kelly Etz’s Fall Uniform

SHOP THIS LOOK: Slouchy Top; Mira Booties; Oversized Shopper


Favorite fall footwear and how you style it: I didn’t think I was a bootie person, but this Sole Society pair is here to change my mind. Ridiculously comfy and easy as throw-on-and-zip, they’ll work with all my go-to fall outfits — dark rinse denim, plaid button downs, slouchy knit sweaters. Plus, the color is :heart_eyes: . Neutral, without being boring. The ultimate win.

What you’re looking forward to most about the season: Fall, to me, means freshness, cleansing, crisp air on rosy cheeks. I always look forward to the feeling at the change of seasons — that enlivening burst of transitions. Plus, leaf-peeping and apple pie.

Go-to fall comfort food: Rosemary mashed potatoes. And all the bread. Always, forever, all the bread.

Perfect fall Day: Hot coffee to cut the cool air. Winding drives through autumnal colors. Breaking bread (yum, bread) with close family and friends. Rich red wine and rambling conversation.


Social Media Manager Caitlin Brown’s Fall Uniform

SHOP THIS LOOK: Natasha Booties; Tan Faux Leather Jacket


Favorite fall footwear and how you style it: Even though I’m only 5’7, I generally like to avoid heels because they make me feel like I’m towering over the rest of the world (it’s a weird complex). I LOVE that these booties are flat but still stylish (so much harder to find than it sounds!) because they feel really casual and easy, but still polished enough to step up my typical jeans and t-shirt.

What you’re looking forward to most about the season: Long drives with a hot beverage to admire the color change.

Go-to fall comfort food: Butternut squash soup. I’m salivating just thinking about it.

Favorite nostalgic song: New Slang by The Shins immediately transports me to high school and walking to the coffee shop right by my school before homeroom. Ah…the days when life was easy but we all thought it was hard.


Your turn! What’s your go-to fall footwear, and how are you styling it this season? Leave us your tips in the comments below! 



This post was in partnership with Sole Society, but all of the opinions within are those of The Everygirl editorial board.