3 Fun Outfits Featuring Pants Tucked Into Boots

After unearthing a forgotten pair of knee-high boots during a recent move, a memory of a woman I once saw on the subway flashed through my mind. She had gray hair, carried an umbrella, wore a crossbody bag with the newspaper sticking out and — the clincher! — had tucked her baggy velvet pants into low-heeled knee-high boots. She looked comfortable, powerful. She seemed the epitome of elegance.

Pants-in-boots (PiB, from here on out) always make me think of strong women on horseback, their trusty steeds galloping through the mud. They make me think of Amelia Earhart; of women stomping in puddles on their way to work, riding bikes up rocky trails and climbing mountains. When I see a woman with PiB, I hear her outfit whisper, “I can do it myself, thank you very much.”

I heard this same whisper as I watched the FW18 runways: Tibi, Ferragamo, The Row, Jil Sander, Zimmermann, Armani (and more) each showed their version of modern power-suiting, PiB capping off all the looks. Together they served as a reminder to go forth and conquer without worrying about wet hems or cold ankles. If you’ve found yourself newly interested, like me, in exploring your freedom via PiB, here are some looks to get your outfit cogs whirring.

The Put-Together Athleisure-ist

Rosie Assoulin tucked sweatpants into knee-highs this Fall 2018 season, but because I don’t wear sweatpants (we can talk about that another time), I settled for a track pant. If you want to make an outfit like this feel fancier, add sparkles and a pleated blouse. To ensure the pants stay inside your boot of choice, I suggest tucking the hems into socks.

The Eclectic Southern Belle

Don’t I look like I love a mint julep? Once your pants are in the boot, pull them up a bit to make them blouse (see above). The volume around the knee makes the outfit look more intentional and less “I’m running out to get the newspaper.” This is also a great way to wear another trend: cowboy boots. (As for the leopard-on-leopard-plus-stripes, I recommend going all out.)

The Art Fair Enthusiast

For an understated option, wear mid-calf or tall ankle boots that match your pants to create a subtle tuck. If you’re working with shorter boots, you’ll need a longer pant leg, otherwise you’ll have to shove the hems in every time you sit down. Tip: I find that securing the ends of my pants with a super loose rubber band helps keep everything in place. For the shirt, layer a fitted top over an oversized button down to manage volume.

Try these with the pants and boots you have at home — maybe you’ll inspire another subway passenger to experiment with her pant collection. And if you’re trying it right now, upload a photo. I’m always looking for more inspiration.

Photos by Edith Young. 

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