3 Non-Intimidating Ways to Wear Over-the-Knee Boots

How to Wear Over-the-Knee Boots at Work

Those tailored work pants are about to get a whole lot more interesting with over-the-knee boots thrown into the mix. To create a look that fuses equal parts polish and style, add in a button-down in soft flannel fabric layered underneath a rich, autumnally hued blazer. Bonus points for long-line styles. Complete the getup with smart tech accessories and a bright carry-all.

Oasis Over the Knee Block Heel Boots ($171) + Mango Combi Print Trousers ($70), Zara Long Blazer With Flap Pockets ($150), Reversible Vegan Leather Tote Bag ($59), Madewell Flannel Sunday Shirt ($88), Ringly Bluetooth Smart Ring ($260)

How to Wear Over-the-Knee Boots on a Night Out

Cold-weather dressing is all about balance. Keeping warm and cozy means lots of layering, but that doesn’t have to mean frumpy and bulky. Over-the-knee boots keep legs covered and looking chic, while a turtleneck and printed mini-dress combo feels sophisticated and incredibly of the moment. Playful accessories like a colorful faux fur coat and metallic clutch infuse the look with personality and drive it well into par-tayyy territory.

Oasis Over the Knee Block Heel Boots ($171) + Topshop Multi-Colored Faux Fur Coat ($170), Selected Femme White Cathy Shift Dress ($100), J.Crew Tippi Mockneck Sweater ($70), ASOS Harmonic Zip Top Clutch Bag ($33), BCBG Double-Wrap Whipstitch Belt ($68), Joomi Lim Lost Innocence Spike and Chain Earrings ($60), Bobbi Brown Long-Wear Gel Eyeliner ($25), Christian Louboutin Nail Color ($50)

How to Wear Over-the-Knee Boots on the Weekend

Off-duty isn’t all joggers and sweats. There is some serious style to be had during those off-the-clock hours, and statement steppers are good place to start. Pair them up with mist-hued skinny jeans and an oversized, grid-check top for the ultimate fusion of casual and cool. Shearling introduces a rustic edge to the look, while funky shades and colorful, high-shine accessories keep it real.

Oasis Over the Knee Block Heel Boots ($171) + Mother Denim The Looker Ankle Fray Jeans ($180), A Common Space Plaid Fringe Shirt Dress ($68), Topshop Faux Shearling Car Coat ($150), Friends With Benefits Taylor Headphones ($200), Quay Australia Westend Girl ($50), Furla Metropolis Shoulder Bag ($498), Olympus Pen E-PL7 Camera ($500)

What pieces in your closet deserve more attention, but stump your style game? Tell us about your trickiest wear-again garments in the comments below and we might feature them in our next Style Resolutions post!