How to Wear Leggings With Boots

Cognac riding boots with black leggings create a distinctive contrast.
Cognac riding boots with black leggings create a distinctive contrast. (Image: kkgas/iStock/Getty Images)

From eye-catching over-the-knee styles to versatile and comfortable booties -- and all lengths in between -- boots pair well with leggings and tights for a comfortable and fashionable cold-weather look. Dressed up for the office or date night and dressed down for a casual afternoon, leggings and boots are versatile styles that can be mixed and matched in many ways.

Classic Combinations

The leggings or tights and boots combination can be dressed up or dressed down, with classic styles of boots creating looks for both day and night.

  • Casual equestrian: For a relaxed but polished look, pair chocolate brown or cognac riding boots, which hit at the knee, with black leggings, a tunic and a fitted blazer.
  • Comfort and function: Flat, slip-on ankle boots in a neutral brown or black can be your go-to shoe when you're seeking serious comfort. These functional boots are ideal for walking, and they work well with a coordinating pair of leggings.
  • Dressy looks: Invest in a pair of patent leather knee-high boots, which are versatile and can be worn with both tights and leggings. Choose a heel height that is comfortable for you.

A Pop of Color

Adding color to your bottom half is simple with both leggings, tights and boots:

  • Bright boots: A colorful pair of boots, such as mid-calf red suede boots, add some intrigue to an otherwise basic neutral outfit.
  • Colorful tights or leggings: Neutral boots and dresses or skirts pair well with colorful tights. Look for a seasonal hue -- in fall, incorporate a pair of burgundy cable-knit tights with cognac riding boots. In winter, consider a jewel-toned jade or amethyst pair of leggings with high-heeled, knee-high black boots.

The key to incorporating colorful boots and tights is to balance the colorful item with neutral pieces. In other words, don't wear bright red leggings and boots -- instead, pick one item to make your outfit pop.

Style Mixing

Your leggings and tights can mix up an ordinary outfit. A pair of black combat boots creates an interesting juxtaposition with tights and a fitted dress or skirt. While this look might not work in the office, it can be a creative blending of trends for more casual days.

Wear a structured tunic and blazer -- a classic combination -- with a pair of floral or tribal print leggings. Opt for a neutral pair of high-heeled booties or riding boots to complete the look. This festive look works well for a party, date night or evening out.

Bold Statement

The right combination of leggings and boots can create a striking look.

Consider metallic ankle boots in shades of silver or gold. These shiny boots make a bold statement and are often accented by distinctive buckles and straps. Wear them with a neutral -- black, brown or gray -- pair of leggings to let the boots be the star.

Dress up an outfit with a pair of black lace leggings and a matching pair of high-heeled ankle boots, which will elongate your legs.

Create contrast by combining a neutral pair of leggings or tights with edgy embellished booties with a chunky heel. Whether you choose a pair of animal print booties or ones with distinctive metal trim, you'll shake up the typical leggings-and-boots combo with this look.

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