8 Leather Boots That Will Make Your Legs Look Amazing

Autumn fashion outfit

Woman wearing leather boots | iStock.com/Voyagerix

Leather boots can be one of the most fun items to unbox once fall arrives. If you have a pair you love, it’s likely they figure into one of the first outfits you choose as the weather begins to get cool. But maybe you don’t have a pair of boots you love. And maybe you aren’t entirely certain about which style would be the most flattering on you. Don’t worry, we’re here to help.

There’s no magic formula for determining which leather boots are going to make your legs look amazing. In fact, factors like boot height, the height of the heel, and how closely the boots fit at your ankle and around your calf all play a role. For many women, a pair of tall boots that hits a couple inches below the kneecap will be the most flattering, since they’ll sit neither too high nor too low on the leg. Looking for more specifics? Who What Wear’s Meghan Blalock has some specific recommendations for the boot style that’ll be the most flattering on different body types.

But depending on your body type, preferences, and how many style “rules” you really feel the need to follow, just about anything goes. Read on to take a look at our pick of the leather boots that will make your legs look amazing this fall and winter. Whether you have narrow calves or wide calves, long legs or short ones, you’re sure to find a style that works well for your proportions and blends in with the rest of your wardrobe easily.

1. Rag & Bone ankle boot

Rag & Bone Harrow suede ankle boot

Rag & Bone ankle boot | Neiman Marcus

The Harrow Suede Ankle Boot from Rag & Bone may be the perfect style for you if you want an ankle-height boot with a high heel. This boot features a 3.5-inch heel and a 5.5-inch shaft. The camel suede is a perfect shade for fall, and offers some great contrast against dark blue or black denim.

2. Frye mid-calf boot

Frye Natalie Mid Engineer boot

Frye Natalie Mid Engineer boot | Neiman Marcus

The Natalie Mid Engineer Boot from Frye is a classic style made of soft calf leather. With a 1-inch stacked heel, a 13-inch shaft, and a 9.6-inch circumference, this style offers a slimmer take on Frye’s Engineer boot. The style features a round toe, two buckle straps, and a pull-on style. It’s perfect to wear with jeans this fall.

3. Franco Sarto block heel bootie

Franco Sarto Granite Block Heel Bootie

Franco Sarto Granite Block Heel Bootie | Nordstrom

The Granite bootie from SARTO by Franco Sarto is a super-low, ankle boot style. With a 2-inch heel and a 3-inch shaft, this is an easy style to wear every day. It has a slim almond-toe silhouette and a stacked block heel. The suede upper is offered in a variety of great colors, which makes it easy to find the perfect shade for you.

4. MICHAEL Michael Kors leather booties

Michael Kors Denver Leather bootie

Michael Kors Denver Leather Bootie | Neiman Marcus

The Denver bootie from Michael Kors is a flattering ankle-height boot for women of all body types. This style features a 3-inch block heel and a 4-inch shaft, plus an almond toe. The dark caramel color is a great match for a variety of different outfits, and the rubber outsole means secure traction even in less-than-ideal fall weather.

5. Rag & Bone black ankle boot

Rag & Bone Walker Leather ankle boot

Rag & Bone Walker Leather Ankle Boot | Neiman Marcus

The Walker Leather Ankle Boot from Rag & Bone offers an edgy take on the classic Chelsea boot. The style features a 1.5-inch stacked heel and a 5-inch shaft, plus a round toe and gored side inserts. A pull-tab at the backstay makes them easy to put on, and a padded footbed makes the style comfortable to wear all day.

6. Frye riding boot

Frye 'Melissa Button' Leather Riding Boot

Frye Melissa Button Leather Riding Boot | Nordstrom

The Melissa riding boot from Frye is a perennial favorite among riding boot styles. This boot features a 1-inch heel and a 15-inch shaft. The classic style and burnished leather offers a vintage look, and the natural hide offers a look that’s unique to each pair.

7. Blondo riding boot

Blondo 'Velvet' Waterproof Riding Boot

Blondo Velvet Waterproof Riding Boot | Nordstrom

This waterproof boot from Blondo offers a sleek silhouette and equestrian-inspired details. This style features a 1.5-inch heel and a 16-inch boot shaft, with either a 14- to 15-inch circumference or a 16- to 17-inch circumference. The leather is waterproof and seam-sealed, which makes it the perfect boot for fall and winter wear.

7. Frye over-the-knee boot

Frye Clara Leather Over-the-Knee Boot

Frye Clara Leather Over-the-Knee Boot | Neiman Marcus

The Clara boot from Frye offers a well-constructed take on the trendy over-the-knee silhouette. This style features a 1.5-inch stacked block heel, plus a 21-inch shaft with an 11.4-inch circumference. These boots also feature a round toe and a vented topline, plus a side zip that makes them easy to put on and take off. You’ll want to wear them all season.