Over-The-Knee Boots Used To Intimidate Me, But Now I Wear Them With Ease

Every season, I attend runway shows for a sneak preview of the upcoming fashion trends for next season. Because of this, I’m always noting down what pieces I’d want from the new collections — the list is long — or scouring Moda Operandi to see if the brand made it into its trunkshow, so I can preorder the item. However, I rarely make the purchase (I have self control!) and often wait for the piece to go on sale. This is precisely how, with patience and luck, I purchased my dream pair of floral, leather, over-the-knee boots from Tory Burch’s Fall/Winter 2020 collection almost two years after I first saw them on the runway. (In the interim, I had thought about them relentlessly.)

After I acquired the beautiful boots in the green colorway, however, I had a realization: purchasing them was easy, but styling them was rather tricky. Truth be told, the boots sat in my closet for all of winter 2021/2022 because I could not figure out how to wear them without buying new clothes. They simply did not work with my existing wardrobe. I thought about selling them after awhile, but with the return of over-the-knee boots as a fashion trend this season (ahem, see Kim Kardashian’s latest footwear campaign) I took it as a sign from the fashion gods to keep the shoes. I made the decision to not let these babies intimidate me, and embrace the fact that the OTK style would look unique with my cold weather outfits. Plus, I still loved the boots so I wasn’t quite ready to part with them.

This time around, when figuring out how to style the shoes, I kept the pressure off myself from feeling the need to reinvent the wheel. Over-the-knee boots, on their own, already make an impactful fashion statement. With this in mind, over the weekend I rummaged through my tiny closet for several fall staples I could pair with the shoes, so that the outfits felt wholly me and not too trendy.

Ahead, you’ll see the fruits of my labor and, perhaps, garner fresh ideas for how to style your very own pair of OTK boots this season. (I’ve also tracked down my exact Tory pair on super sale, but there are only a few sizes left. Additionally, you can find them on secondhand sites, like Poshmark.) You’ll catch me wearing the effortless ensembles, below, on date nights, into the office, and to New York Fashion Week February 2023.

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Underneath A Knit Dress

Your first instinct in wearing over-the-knee boots might be to tuck a pair of bottoms into the footwear, but you don’t have to do so. Instead, take your cues from a few Tory Burch runway looks and style the shoes underneath a billowy dress or slit skirt, so you can still get a glimpse of the OTK design. I had this gray knit dress (and older piece from Zara) in my closet that was perfectly roomy enough to layer over my boots. An Oak + Fort mens trench coat completed the look.

With A Hoodie, Jeans, & Coat

Since this particular pair of boots had a very narrow and long shaft, it required me to wear a pair of formfitting bottoms, namely my long forgotten black skinny jeans. (I know, this denim style isn’t popular anymore but they were the only pants that fit inside the boots!) I wanted this ensemble to look laid-back — the type of outfit I’d throw on after work on Fridays to meet up with friends — so I wore my H&M x ERDEM hoodie for comfort underneath my R13 trench coat.

With A Blazer, Sweater, & Leggings

I’ve only worn leggings into the office a handful of times, as they don’t often feel appropriate for work. However, when I styled it with OTK boots and an oversized blazer (that covers my bum) from Deadwood, that’s a different story. Suddenly, my leggings look less casual than purposeful in my outfit. For extra security in the butt-coverage area, I wore a semi-lengthy 3.1 Phillip Lim thick cable knit sweater underneath my blazer.