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What not to wear with thigh-high boots?

Thigh-high boots are having a major moment right now. From skinny jeans to mini skirts, these sexy boots elongate your legs and add serious style to any outfit. But styling thigh-high boots can be tricky. If done wrong, your look can appear sloppy or even inappropriate. Follow this guide on what not to wear with thigh-high boots for effortlessly chic ensembles.

Avoid Baggy Pants or Shorts

Thigh-high boots already have a lot going on visually. Pairing them with baggy pants or shorts overwhelms the look and hides the sleek silhouette of the boots. Opt for skinny jeans, leggings, or a body-skimming mini skirt to balance the over-the-knee style.

Don’t Wear Thigh-High Boots with Short Skirts or Dresses

One of the most common thigh-high boot mistakes is wearing them with skirts or dresses that are too short. Here are some guidelines on skirt and dress lengths:

  • Mini skirts should hit mid-thigh when worn with thigh-high boots. Anything shorter tends to look tacky.
  • Dresses and tunics should hit no higher than a couple inches above the knee.
  • Go for sleek, form-fitting styles instead of loose, flowy silhouettes that can easily fly up.

Showing too much upper thigh overwhelms the look. The boots themselves make enough of a statement, so the rest of the outfit should balance it out.

Avoid Excess Fabric Around Thigh-High Boots

Too much fabric bunching around the shaft of the boots looks sloppy. Thigh-high boots have a smooth, sexy silhouette that is best shown off by streamlined styles.

If you want to wear a skirt or dress, choose form-fitting options that won’t gap or sag around the thighs. Loose-fitting pants should be tucked into the boots or rolled up above them to maintain a sleek line.

Don’t Wear Fitted Mid-Calf Boots

Wearing fitted boots that stop mid-calf completely cuts off the long vertical line created by thigh-high boots. This chops your leg in half visually. Mid-calf boots can work with thigh-highs if they are slouchy flat booties, but avoid fitted styles.

Avoid Super Casual Styles on Top

Thigh-high boots make any outfit instantly dressier. Don’t wear them with super casual tops like hoodies, sweatshirts, and t-shirts. The mix of fancy and casual is confusing.

Save thigh-high boots for date nights, parties, and occasions when you want to take your look up a notch. Pair them with blouses, blazers, and other elevated tops.

Skip Thigh-High Boots with Mini Skirts If You’re over 40

One of the most flattering ways to wear thigh-high boots is with a mini skirt. But traditionally “sexy” looks like this don’t tend to work as well after 40.

The mini+boots combo can still look amazing, but focus on age-appropriate styling. Opt for a skirt that hits a couple inches above the knee in a structured fabric like leather or ponte knit. Pair it with a cami and blazer on top for a vampy yet sophisticated ensemble.

Don’t Wear Thigh High Boots with Baggy Shirts or Sweaters

Thigh-high boots demand sleek, form-fitting styling from head-to-toe. Baggy tops conceal your figure rather than complementing it.

Look for slim-fitting styles when choosing tops, especially through the hip and thigh area. Well-tailored blazers, silky camisoles, and crisp button-down shirts balance perfectly with thigh-high boots.

Avoid Thigh-High Boots with Low-Rise Jeans or Trousers

To elongate your legs, high-waisted bottoms work best with over-the-knee boots. Low-rise styles visually cut you in half, which shortens your silhouette.

High-waisted skinny jeans, trousers, or leggings will streamline your shape and show off the boots to their full potential.

Don’t Pair with Baggy Layers on Bottom

Thigh-high boots already add visual weight to your lower half, so baggy layers like voluminous skirts or wide-leg pants tend to overwhelm the look.

Keep your bottom half streamlined in pencil skirts, skinny jeans, leggings, or slim-cut trousers. This creates an elongated silhouette.

Skip Thigh-High Boots with Ankle Boots

Layering thigh-high boots over ankle boots may seem like an edgy style choice, but it rarely works. Ankle boots chop up the sleek line of the thigh highs.

Opt for one tall boot statement at a time. Ankle booties can look great with a shorter skirt or cropped jeans. Just avoid pairing them with thigh-highs.

Don’t Wear Thigh High Boots with Baggy Layers on Top

Thigh-high boots command attention, so top-heavy layers tend to overwhelm them. Steer clear of statement sleeves, ruffles, puffy jackets, or anything voluminous.

Let the boots be the focal point by keeping your tops streamlined. Go for sleek silhouettes and lightweight fabrics up top.

Avoid Visible Socks

Visible socks peaking out of thigh-high boots breaks up their elongating effect. If your boots have a wide shaft, look for thigh-high stockings that can be tucked in to cover any gaps.

For boots with a narrower shaft, seamless footie socks that don’t fold over work best. The goal is to extend the long, lean line of the boots all the way up the leg.

Don’t Wear Thigh-High Boots with Short Jackets or Cropped Sweaters

Cropped jackets and sweaters are too short to complement the dramatic height of thigh-high boots. You want to extend your silhouette rather than cutting it off.

Look for jackets and sweaters that skim the hips or land at mid-thigh. This maintains the streamlined effect of the boots.

Avoid Pairing with Overly Distressed Denim

Trendy thigh-high boots should take center stage in your outfit. Jeans with heavy distressing, embellishments, and funky prints compete for attention.

Opt for solid classic washes in dark denim without elaborate details or fading so the boots stand out.

Don’t Wear Fitted Boots Over Thigh High Boots

Trying to layer fitted boots over thigh-high boots not only looks silly, it’s uncomfortable! The shaft of thigh-high boots is meant to skim your actual thighs.

Save layered boot looks for slouchy over-the-knee flat booties instead. They have more room in the shaft to accommodate another fitted boot underneath.

Conclusion

Thigh-high boots make a bold statement, so it’s important to style them properly. Follow these tips on pieces to avoid, like short hemlines, baggy layers, bulky fabrics, and mismatched boot heights. Streamlined, figure-flattering styles allow the boots to shine.

With the right outfit formulas focused on sleek silhouettes and vertical lines, you can wear thigh-high boots confidently. Just beware of unnecessary details or proportions that will clash with the drama of the boots themselves.