What To Wear With Every Style of Boot
One of the things that gets everyone so excited for fall weather isn’t just the gorgeous changing of the leaves to brilliant gold and crimson, the multiple opportunities for autumnal events (hello, apple picking and pumpkin carving!) or even the much-anticipated arrival of everyone’s favorite seasonal specialty (we’re looking at you, Pumpkin Spice Lattes). No, it’s the return to a style of dressing that manages to combine the best of both worlds—one part cozy and comfortable, and one part effortlessly chic—that can only be accomplished by the skilled layering of cool-weather essentials like sweaters and knits, and accented just-so by our all-time favorite footwear—boots.
As much as we love them, boots (from the lowest ankle boot to up-to-here thigh highs) pose a wide array of problems for many. Unlike sneakers or ballet flats, you can’t just pull them on with any ensemble and call it a day. Their varying heights and proportions work well—or not at all—with certain clothes, and the dizzying number of boot styles and outfit combinations can leave one’s head spinning.
But not to worry—we’re here to help. Whether you’re looking to put your best foot forward in you trustiest pair of traditional riding boots, or you’re ready to pull the proverbial trigger on a brand new, fashion-forward, over-the-knee suede style, we’ve created a cheat sheet for every type of boot, both the high heel and the flat varieties. Click through for styling suggestions that range from just right for casual weekend errands to totally on point for your next big presentation at the office, along with other helpful info like fit tips and outfit suggestions.
These low-profile boots come in both flat and heeled styles that can be equally flattering. Flat ankle boots often have a much more rugged vibe, while pointed, heeled styles come across as more ladylike.
- Skinny jeans or leggings that fit close to the ankle, so they slip just inside the tops of the boots.
- Wide-leg or flared trousers with pointy-toed ankle boots. The pants should just skim the floor, with the toe of the boot peeking out in front.
- Of-the-moment skirt silhouettes, like full midi skirts or pencil skirts that hit below the knee. The longer cut looks more refined (and less retro) than mini skirts when paired with a heeled ankle boot.
To buy: Vionic Upton Ankle Bootie, $160; shoebuy.com.
A potentially tricky style to pull-off, since they cover what is the slimmest part of most people’s legs, there are still many ways to wear medium-rise boots.
- Ankle-length skirts that fall just an inch or so below the top of the boot, for a look with a slightly 70’s feel that showcases your footwear.
- Boot-cut jeans. This denim silhouette is so named because it is specifically meant to fall over calf-high boots (thus the extra, flared room toward the bottom the leg).
- Mini skirts with heeled mid-calf boots. Because this shoe does cut across the widest part of the calf and hide the ankle, a few extra inches go a long way toward elongating legs, and exposing the other narrowest part of the leg (just above the knee) will help make your stems look more shapely, less straight up and down.
To buy: See by Chloe Studded Buckle Booties, $450; anthropologie.com.
Styles like riding boots that hit just at or below the knee are a classic for a reason—they look good on most people and with most outfits. While heeled options can run the risk of looking a bit dated, traditional flat styles are always a good pick.
- A classic equestrian look: Flat, black leather boots pulled over leggings. Bonus points for a jacket that hits mid-thigh and a sleek chignon to pull the look together.
- A pair pulled over skinny jeans, and layered with fall favorites like a flannel shirt and slouchy sweater or a cape, for a casual cool-weather look.
- Specifically cut, wide calf styles if a straight cut feels (or looks) to tight—the extra room will also open up your outfit options so you can tuck in jeans or thick knit tights.
To buy: LAUREN Ralph Lauren Mackenzie Wide Calf Boots, $159; zappos.com.
An increasingly popular style that’s become as popular as traditional to-the-knee boots, this length’s proportions feel a little more modern, whether heeled or flat, and has the added element of making legs look longer.
- Flat styles pulled over skinny jeans or leggings, and paired with a long sweater or a tunic top.
- Heeled styles paired with a mini skirt that just grazes the tops of the boots to create a layered look that shows off the style without leaving you exposed.
- Dressing down this fashion-forward style by pairing them with unexpected, cozy pieces, like a sweater dress.
To buy: Chinese Laundry Kiara Over the Knee Boot, $100; chineselaundry.com.
Just because the weather is bad doesn’t mean your footwear has to be. Rain boots have come a long way from the days of heavy, poorly-fitting galoshes available only in muddy brown or green rubber. You don’t have to worry about changing your shoes once you get to the office or inside, you can wear these new, stylish versions all day long (and even into the night).
- Ankle-height styles made to look like everyday footwear, paired with your favorite skinny jeans.
- Knee-high styles in unexpected colors, patterns, or textures, pulled over leggings and paired with a tunic-length sweater.
- Equestrian-inspired styles worn with skirts or dresses.
To buy: Bernardo “Peony” Rain Shoe, starts at $100, amazon.com