The 5 Best Women’s Boots for Fall and Winter

These boots are super cute…

By Hannah Rogers |


Everyone needs a good pair of boots (or five!). And with winter on its way, cute boots should definitely be at the top of your shopping list. From trendy ankle booties to fashionable over-the-knee styles, here are the best boots for this season.

Over-the-Knee Boots

In the past, over-the-knee boots had a racy reputation. But today, they couldn’t be more modern, fashionable, and chic. Tuck in a pair of colored skinny jeans, or wear with a skirt and tights. A plaid blanket scarf will add softness to your look.

Riding Boots

Classic and timeless, riding boots are a staple for fall and winter. Whether they are chestnut brown, jet black, or a shade of taupe-gray, riding boots are always in style.  Just be careful to not look too much like an equestrian – if you are wearing riding boots (especially ones that have stirrup details at the top), stay away from equestrian-style leggings or fitted blazers (or else you’ll look like you’re off to meet Seabiscuit!). Instead, opt for more modern pieces like black ripped skinny jeans, a rich-toned floral top, and dainty accessories.

Midi Boots

Midi boots are also in style this season, especially ones with moto-like buckles or laces. Pair these with a fall frock and tights, or with cropped denim.

Ankle Booties

Booties are the most popular type of boot this fall. From fringe to buckles to soft suede, ankle booties come in a diverse number of styles, textures, and colors. They also go with everything – flares, tight jeans, dresses, skirts, you name it ­– making them an absolutely necessary wardrobe staple this time of year.

Chelsea Boots

Chelsea boots are back! First made popular in the 1960s, the Chelsea boot has always been a sleek and sophisticated slip-on shoe. We adore pairing them with high quality leggings, a cozy flannel, and a cool denim jacket. Or, try wearing a pair with a bohemian maxi skirt and off-the-shoulder sweater.

Go ahead – get your booty into some boots! Each of these styles are a worthy wardrobe investment; boots last a long time, and will carry you through winter. Trust us – your closet and wallet will thank you.