We all know the iconic paparazzi snap. A baseball cap, simple black blazer, and bright-white sweatpants tucked into a pair of saddle-brown leather cowboy boots. It was Princess Diana, it was the ’80s, and it was glorious. The look was fitting for the time when MC Hammer was dancing across our MTV-tuned television screens in brightly-patterned harem pants with a similar silhouette to Diana’s. Of course, as it always goes, our pant shapes changed and both baggy and then skinny jeans became en vogue (jeggings, if you will). Once the early aughts passed by and we began our current cycle of trends, cropped flares were embraced, especially with an ankle boot accessorized underneath to accompany. This pairing has served us well for the last several years thanks to its elongating lines and versatility, but if street style is any indication of what’s on the horizon—and it usually is—we’re in for a shift.
The latest snaps from fashion week have shown editors, stylists, and the like tucking their pants into their boots. The result is surprisingly very refreshing and not as man-repelling as you might presume. A couple of things to keep in mind if you’re giving it a go; first, pick a boot that hits at your shin or above. If it’s a super low cut you won’t get the full effect and it might just look like you skipped out on your tailor. Second, choose materials that will drape into footwear easily. A pair of stiff corduroys, for example, is not the best option. Lastly, get creative with the color palette. You’re already trying out something new, might as well double down and make it look intentional.
Ahead, a handful of outfits that translate this ’80s-inspired styling trick to 2019, and a few boot and pant pairings to shop for the new season ahead.
If you’ve ever pondered over how to wear python-print pants, ponder no more.
Tuck a pair of khaki pants into knee-high boots for some subtle Amelia Earhart vibes.
Denim on denim is always a win—give yours an update by tucking your jeans into some bright boots.
You already know mixing and matching prints is a thing, but did you know your footwear can get in on the action? See above.
Just when you thought you’d heard the end of the cowboy boots trend.
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