9 Incredibly Cute Knee-High Boots Outfits to Keep in Your Rotation

It's the shoe of the season for a reason.

Person wearing a Knee High Boots Outfit, including a peach dress, tan jacket and white boots
Photo: Jeremy Moeller/Getty Images

The change in seasons doesn't necessarily have to translate to an overhaul of your wardrobe. Many autumnal staples, for example, serve as winter essentials, too. This comes in handy when you're mourning the end of cool breezes and colorful leaves — and therefore dreading biting windchill and shorter days. Here's a silver lining: you can still enjoy some of your favorite pieces amidst the colder forecasts, like sweater dresses and shackets, blanket scarves, and, my personal favorite, knee-high boots.

Knee-high boots fall under the same category as printed jeans and all things Ugg — they're articles of clothing that can take functional winter outfits and make them fashionable. They serve a purpose — the more material riding up the leg, the warmer said leg will be in frigid weather conditions — but they're also stylish, so you don't have to sacrifice looking good in order to survive below-freezing temperatures.

Oftentimes, the go-to knee-high boots outfit is a simple one: styled with denim, usually skinny jeans, and worn with an oversized sweater. This is all well and fine (and, admittedly, a staple in this writer's closet), but there are a plethora of other knee-high boots outfits just begging to be worn. Ahead, I've rounded up a few of my favorite pairings to inspire your day-to-day uniform for the colder months.

With a Romper

Here at InStyle, we worship a done-in-one outfit, where the only area you really have to put effort into is your accessories. Rompers are the perfect example of this: simply slip into your favorite and you're practically out the door. Sneakers are a go-to pairing with these pieces if you want to keep things casual in the heat, but if you'd like to enhance your ensemble and make it work for chillier days, opt for knee-high boots (and even a pair of tights) for added high and contrast.

To Add Coverage to a Mini Skirt

Mini skirts are too cute to pack away for the entire winter, but while they pair well with tucked-in oversized sweaters, that sweet aesthetic won't keep you warm. Layering up is key — think thick pairs of tights and leg warmers — but beyond hosiery and socks, knee-high boots also act as a shield from the cold.

With Leggings

Boots and leggings attract like magnets, and the look can be dressed up, down, or sporty. The combination also makes for the perfect throwback fit if you're channeling the late '80s fashion or early '90s trends with a matching quarter zip, puffer jacket, and a headband.

With a Sweater Dress

Basic? Maybe. Classic? Absolutely, so don't sleep on this cozy-cute combo. It's an easy put-together look you can wear to brunch with the girls, date night with that special person, to the office, or running errands.

To Dress Up a Shirt Dress

Depending on the shirt (i.e. a button-down, oversized sweater, or graphic tee), shirt dresses alone can give off a casual vibe. Adding a knee-high boot could change the entire aesthetic. A skinny or chunky heel will make you feel a little fancier (not to mention give you a little lift), while something like a cowboy-style boot will add some flare.

For Contrast to a Cozy Cardigan

If the past few years taught us anything, it's that being cozy should come first, no matter what occasion you're dressing for. Being comfortable is undoubtedly the key to feeling your best, but you don't have to sacrifice style in doing so. The trick? Pair a cozy staple with something a little more dressy, like a knit cardigan and sleek knee-high boots.

As an Extra Layer Under Long Skirts

In order to survive harsh winter weather conditions (re: freezing cold temperatures), layering up is imperative. So while you might associate knee-high boots with mini skirts to give your footwear the utmost exposure it deserves, utilizing them as an extra layer of warmth under a midi or maxi-length skirt or dress is actually a pretty genius move.

For a Lampshading Moment

I'm well aware that Ariana Grande didn't invent lampshading, but she definitely brought the trend back. To master the art of lampshading is simple: Pair an oversized sweater or hoodie with knee-high or over-the-knee boots and strut with confidence. You'll definitely want to add a long coat and tights to the mix if temperatures start to dip in your neck of the woods.

Make It Sporty

If when you think of knee-high boots you think of sleek ensembles, you're not alone. This type of footwear does lean more formal, but it has a sporty side, too. Pair your favorites with workout leggings and a hoodie, layer with an oversized puffer vest, and top off the look with a beanie. The finished product is polished but super lax, so you can look and feel cool, calm, and collected while checking things off your to-do list.

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