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The Right Way to Wear Leggings

NancyAdd some classy warmth to your winter wardrobe

First introduced in Scotland in the 14th century, leggings were originally designed as two separate pieces – one for each leg. In fact, until the 18th century, it was typically men who wore leggings, from the Renaissance period through Shakespeare’s day. They were first considered fashionable for women in the 1960s, when they started showing up in retail stores.

Over the past few decades, the diversity of outfits with leggings has increased dramatically. Worn prominently over the years by social icons like Debbie Harry and Madonna, leggings have proven they are here to stay.

Obviously, fashion trends have shifted since then, and we’re here to give you some creative ideas for sophisticated outfits with leggings this winter. Understanding the different types of leggings is key to knowing how to incorporate them into your style.

Types of Leggings

The two things to consider when wearing leggings are: length and material.


The length of the pair can depend on the weather, how casual your attire, or their purpose. The standard lengths of leggings are ankle, capri, & knee – and sometimes they can have a stirrup.


The purpose of your leggings often determines which material is best. Exercise leggings are frequently made from a Lycra or spandex blend (with properties to wick away moisture), while those incorporated into your day-to-day style are typically a blend of cotton, leather, silk or wool. Regardless, they all are intended to be form-fitting and stretchy.

When you plan outfit ideas with leggings for the winter, high-quality, thick leggings are important for both warmth as well as putting together a modern, classy look.

How to Style Leggings

Here are some quick ideas for stylish outfits with different types of leggings:

  • Leather leggings add sass to your ensemble. Add a touch of class by layering on top, with a patterned sweater or an oversized blazer.
  • A loose-fitting chambray shirt or our P. Taylor cardigan sweater looks great over leggings, but the key is to make sure it is long enough. Mid-thigh is the perfect spot for a top to land. Throw on a long scarf or necklace and some boots to complete the outfit.
  • Stylish leggings are perfect underneath your favorite tunic (get options in our online store). Finish the look off with some ankle boots and a long necklace.

Some helpful tips:

  • Leggings are meant to fit snugly, so choose tops that are modest and cover all the right places.
  • While they may serve somewhat similar purposes, tights and leggings are not the same thing. Leggings are cropped below the ankles, while tights cover your feet. Tights are thinner and are not usually worn on their own.
  • Find leggings that are comfortable! Although they are made from stretchy fabrics, pay close attention to sizing charts to ensure the elastic waistband is not too tight.

P. Taylor Classic Shirts: The Perfect Complement

Our stunning Classic Shirts are a simple yet elegant choice to wear with leggings. The oversized look provides modest appeal, without sacrificing the edgy flair of the leggings. Comfortable and stylish, you can’t go wrong when you pair a blouse from our Ruby Collection with dark leggings, or dress up your outfit more with our Washed Silk Classic Shirt.

Shop for your favorite P. Taylor tops today and get ready for a warm, sophisticated look this winter!