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How to Style Knee High Boots

Fashion trends swing back and forth from season to season, but as autumn rolls into the holidays, you can always count on the return of knee-high boots. Kneecap-grazing footwear is a fall-winter staple that pulls even the most casual looks together effortlessly, more comfortable than their thigh-high counterparts, and more versatile than ankle booties. Here are a few go-to outfits to try with knee-high boots as we transition from fall to winter.

The easiest way to wear a knee-high is with a midi hemline, whether it’s an A-line skirt or an oversized sweater dress. You can top off this look with a knitted polo and denim jacket or a turtleneck and blazer. The reason why I like a longer skirt versus a mini or short dress is it gives the leg more coverage. Sometimes, that slice of skin peeking out between the edge of a skirt and the top of a boot just isn’t practical as the weather gets cooler.

For a more casual look, tuck your favorite pair of pants into a knee-high boot and let the fabric pool around the knees. You can pair this combo with a cozy knit and a light jacket on warmer days or a pea coat for chillier weather.

Depending on the boot and pant, you could play with contrasting styles and pair with a hooded sweatshirt and sporty windbreaker. This outfit combo is business on the bottom but fun on the top.

Of course, not everyone appreciates a slouchy look with pants scrunched into boots. You can still wear knee-highs with pants underneath wider-leg trousers. This is especially great with heeled boots where you may need some extra height depending on the pant hem. Style this look with a button-down and sweater thrown over the shoulder. Or wear boots with a standard pantsuit for a bit of edge and extra height.

Not all suits are the same. Take, for instance, the skirt suit, which, when paired with knee-length stilettos, feels appropriate for the office but not too stuffy for a post-work happy hour. There are also short suits, which may not be everyone’s sartorial cut of tea, but if you have a coordinated suit of shorts and a jacket, a pair of knee-high boots extends the wear of that suit into the fall and winter. Trousers shorts on their own can also be worn with knee-length booties and look great with an oversized knit and tights.

If suits and skirts aren’t really in your style wheelhouse, you may want to pair your knee-high boots with jeans. While most people tend to wear boots over skinny jeans, baggy jeans are more on-trend. This boot style works equally well when paired with wide-leg styles. The trick is to opt for a shorter cropped and/or an interesting, cuffed jean to bring attention to the boot. Double down on your denim with a chambray shirt or go for a simple tee and bomber-style jacket.

Lastly, we have dresses. Even though I’m not a big fan of mini-skirts or short dresses for myself personally, it’s hard to deny how good a knee-high boot looks with a shorter hemline. To avoid showing more skin than you’re comfortable with, it’s best to pair minis with tights and looser tops.

For dresses, you can layer with leggings tucked into boots for coverage.

Whether or not knee-highs are on your radar this season. Hopefully, some of these styling tips will make you rethink this fall staple footwear as we head into winter.