Fall in Love With Our Favorite Autumn Boot Styles

Story by Morgan Wood
Photos by Anne Langan

Your boots have been hibernating in your closet for long enough, and now that fall is finally here, it’s time to break them out.

From weekdays on campus to football season’s weekend tailgates, these can take your look to next-level cool.

This season, it’s all about ankle boots, riding boots, rain boots and peep toe booties. Whether you’re looking for new ways to style your old pairs or are searching for something new, we’ve got you covered.

Ankle Boots
Ankle boots are an integral part of a trendy fall wardrobe. Simple yet sophisticated, they’re perfect for creating a casually chic look.

To Style:
Pair with a loose tee, utility jacket (or cardigan) and cuffed jeans for a relaxed look. For a slightly dressier option, pair with a long sleeve t-shirt dress and a plaid blanket scarf.

To Shop:
Opt for a tan or taupe color for optimal versatility. These hues work perfectly with most colors and lighten up your look. In terms of material, suede provides a softer look and a touch of femininity, while leather creates a slightly edgier look. A low heel is also highly recommended – it’ll work wonders for elongating your legs and torso. Try these on for size.


Riding Boots
Riding boots are the most essential boot of fall. Classic and casual, they polish any look.

To Style:
Wear with a plaid button down, black vest and dark wash jeans for a preppy look. For an ultra-comfy and equally stylish look, pair with black leggings and an oversized sweater. A poncho layered over a long-sleeve tee can also be substituted for an oversized sweater.

To Shop:
Consider color, quality, length and details.

Dark brown, cognac and black comply well with a fall color palate. In terms of quality, riding boots should be an investment, so saving and splurging is encouraged. Opt for leather if possible, and reserve pleather for the rain boots below. A riding boot should hit a couple inches below the knee, and leave some breathing room around the calves, (but not too much). Look for minimal details that add dimension to the boots, but don’t overpower its polished aspect. A subtle logo, buckle or strap should do. We recommend these Tommy Hilfiger lovelies.

Rain Boots
Rain boots are an effortless staple that add style, warmth and comfort to any look.

To Style:
Pair with black leggings, a chambray button down and a quilted herringbone vest for a rainy day look. For a second option, layer a black and white, loose fitting stripped tee, under an olive utility jacket and pair with black leggings. If you’re looking to add more detail and warmth to your look, layer cable cuffs or knee high socks under your boots.

To Shop:
Hunter and Coach are excellent brands to purchase rain boots from. If you’re seeking a warmer option, Coach Rain Boots are faux-fur lined. If you’re looking for a variety of lengths, colors and styles, check out Hunters.

However, keep in mind that a black pair will offer the most versatility. You can’t go wrong with these Coach boots.

Peep Toe Booties
Arguably, the best bootie of all.

To Style:
Pair with medium wash cuffed jeans, an off the shoulder top, and a plaid blanket scarf. Another option includes a loose fitting tunic paired with distressed denim, cuffed at the ankles.

To Shop:
Take texture, color and height into consideration. Leather or pleather polishes any look, and cognac or taupe pairs extremely well with fall colors. Don’t sacrifice a high heel height for comfort. Also, don’t be afraid of details like cutouts, straps, and buckles – they’ll add chic edge to your look.

To get your started, DSW has a great pair of Peep-Toes.