Over-the-knee boots in a neutral color like gray are a transitional shoe that will take you into future seasons in style. Flat over-the-knee boots or boots with a chunky heel are the the most universal and will be sure to keep you looking pretty, without being over the top.
A dress in a loose silhouette and a fun color or print adds bohemian flair and is a great backdrop for your boots. To keep a long, fluid line, the hem of your dress should fall one to three inches above the top of the boots. For cooler months, layer tights under your dress. To lengthen your legs, opt for tights in a similar hue to your boots. If your dress is a solid color, try patterned tights to add some personality to your look.
Tunic and Leggings
Pair a tunic and leggings with your gray over-the-knee boots for a casual, layered look that works for daytime. Since your boots are a neutral base, choose a tunic in an abstract print or a pop of color. For added warmth and dimension, add a chunky cardigan in a neutral color that will not compete with your tunic and will complement your boots. Accessorize your ensemble with a statement ring and a long, multi-strand necklace that will mirror the layers of your look.
Fitted skinny jeans are synonymously casual and chic when tucked into your over-the-knee boots. For a rock and roll vibe that will visually elongate legs, stick with skinnies in a shade of gray similar to your boots. Top off the look with a T-shirt showcasing your favorite band or a bold graphic. Indigo denim also pairs well with your boots. For a look that transitions your denim from day to night, layer a loose camisole underneath a fitted blazer. Accessorize with a menswear-inspired watch and a statement necklace.
A feminine flared skirt that falls above the top of your boots displays your over-the-knee stunners, while offsetting their tough girl attitude. Harmonize the look with a Peter Pan-collared blouse. Once cooler temperatures hit, layer a light cable knit sweater over your blouse for a preppy chic ensemble.