Fashion Experts Agree: This Winter Boot Style Pairs Well with Jeans, Skirts, and Leggings

      It's that season again when we pull out our closed-toe, warm, weather-resistant shoes and boots (the clouds are rumbling as I jot this down). Ankle boots and mid-calf styles are ideal for the changing autumn months, especially in suede, but one particular boot style stands out for the colder days ahead: leather knee-high boots. Not only are they currently trending, but knee-high boots also make a versatile addition to your capsule wardrobe, working well with everything from skirts of various lengths to dresses, sweatpants (yes, you read that correctly!), leggings, and even our dependable jeans. I've been wearing a reliable pair of knee-high boots from the popular brand Whistles for several weeks now, and they have become my go-to for everyday outfits. Resting just below my knees, with an almond toe and flat rubber lug soles, they are made from premium black leather. Their design and material make them suitable for any weather, and they can effortlessly elevate casual evening looks as well.

      As I scroll through social media and stroll around London, I've noticed other fashion-forward individuals styling knee-high boots of all kinds in various ways. It's not just about plain, flat options; I've seen a rise in patent, lace-up, heeled, buckled, pointed-toe, sculptural, and form-fitting knee-high boots, underscoring how adaptable this trend is and how well it complements many aesthetics. If you're eager to step out in style this winter, keep reading for seven tips on how to style knee-high boots. Plus, I'll share some of my favorite pairs that you can shop right now.

      1. **Knee-High Boots + Funnel-Neck Jacket + Lace Skirt**

      Style Notes: Just because it’s gotten chilly and rainy doesn't mean you can't dress up. Take a cue from Hannah Lewis and opt for a funnel-neck jacket (buttoned to the top), a lovely lace-trimmed skirt, and shiny knee-high boots with a heel for a chic city look. This serves as a masterclass in how to wear heeled knee-highs in a more formal, day-to-night setting. The monochromatic color scheme keeps this outfit timeless, transitioning seamlessly from meetings to dinner plans.

      2. **Knee-High Boots + Suede Jacket + Blue Jeans**

      Style Notes: I've noticed fashion enthusiasts reviving the Y2K trend of tucking jeans into their boots, and I'm here for it! A bit country, a bit nostalgic, it’s a perfect look for weekends in both the city and the countryside. Opt for straight-leg jeans (which are easier to tuck in) and a boot with a bit of room to maneuver. A skin-tight or sock-boot style won't work here; choose something with space and a chunky sole. A suede or barn jacket completes the look while keeping you warm. Mini sunglasses and a sparkly bag add a Kate-Moss-at-Glasto vibe.

      3. **Knee-High Boots + Matching Set + Sunglasses**

      Style Notes: For a more eye-catching look, consider a lace-up boot, preferably with a sharply pointed toe. The laces can provide an extra visual twist and create the illusion of longer legs. Follow Lily Russo-Bah’s lead and coordinate the rest of your outfit boldly. A pink nylon funnel-neck jacket paired with a matching skirt adds a sporty touch. Don't forget some oversized sunglasses!

      4. **Knee-High Boots + Long Wool Coat + Leggings**

      Style Notes: If your style leans toward moody and cloudy vibes, take note. Pair a slate-grey chunky knit (a roll neck if it’s particularly chilly), plaid shirt, and simple leggings with knee-high boots, just like Ingrid Edvinsen, for a monochromatic, cozy outfit perfect for weekends. A structured wool coat, a black leather bag, and sleek oval sunglasses finish off the look, ensuring it doesn’t appear too disheveled.

      5. **Knee-High Boots + Oversized Shirt**

      Style Notes: While the Glenn Martens x H&M capsule collection is mostly sold out, you can still capture the look. Our junior fashion editor, Imani, was smitten after previewing this collection. Emulate her style with an oversized pinstripe shirt worn like a dress and sculptural knee-high boots for an edgy vibe that's slightly punk.

      6. **Knee-High Boots + Long-Sleeved Tee + Tracksuit Bottoms**

      Style Notes: I didn't anticipate this pairing, but it works! Combining heeled, pointed black boots with baggy tracksuit bottoms and a '90s long-sleeved T-shirt tied with a plaid shirt around the waist is surprisingly chic! On those days when you can't choose between comfort and luxury, wear both. A burgundy handbag and classic Ray-Ban Wayfarers round out this casual look.

      7. **Knee-High Boots + Knitwear + Midi Skirt**

      Style Notes: Marilyn expertly shows how to style