Cold weather fashion trends complement a woman’s individual style and provide warmth in cool temperatures. A popular trend for women during the fall and winter months is to wear a skirt with tall boots. This fun fashion statement is versatile for workplace attire, casual outings and nights on the town. Understanding how to wear a skirt with tall boots will ensure you always look collected, sophisticated and, above all, confident.


Invest in a pair of quality high boots. A “high” boot is classically defined as a boot that reaches the knees. The boot should fit snugly around your calf. Consider a style that is neutral in color such as brown or black and made of leather or suede to match a variety of outfits, such as Frye Boots. Choose a heel or flat-boot style that fits your personal tastes and needs.

Purchase several pairs of tights. Consider styles by HUE for long-term durability (and plenty of selection). Styles such as herringbone, ribbed, cotton and brightly colored can be easy ways to refresh an outfit or make a statement when wearing tall boots with a skirt. Wear tights or hose with a skirt and boots to avoid revealing bare legs.

Choose a skirt. Consider the function, and pick an appropriate skirt. Work ensembles may require a knee-length or longer skirt, while social events can promote shorter-skirt pairing with tall boots. Skirts that look great with high boots include A-line, full, narrow and short styles.

Outfit appropriately. Work day? Choose a fitted, solid-color knee-length skirt paired with herringbone tights and tall black boots. Date night? Select a skirt that shows off your shape and boosts your confidence, and pair it with brightly colored tights (such as red) and tall boots (with a heel). Running errands? Outfit with function in mind, such as a long, flowy skirt, cotton tights and high boots to keep your legs warm and your body comfortable as you check off your to-do list.

Avoid outfitting pitfalls. Do not outfit in a monochromatic way, such as pairing a black skirt, opaque black hose and black tall boots. Additionally, unless you enjoy rocking out in crazy style, be watchful of mix-and-matching a funky-patterned skirt with bright tights and red vinyl high boots.

Utilize outfitting resources. Study the pages of Vogue and In Style magazines for outfit inspiration, and check out runway shows to learn how professional stylists and designers pair their skirts with high boots. Look for ways to define your own personal style with the classic trend.

Tips

  • Although high boots can cost upwards of $150, the investment should last several years of wear and tear.