How to Wear Leggings Over 50: The Ultimate Guide

How to Wear Leggings Over 50: The Ultimate Guide

Wondering how to include leggings in your daily looks, especially if your are over 50? Read on for some of our favorite tips on how to style these chic, comfortable bottoms!
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Val wearing an aqua top and printed capri leggings

Leggings have been a popular trend since the late 2000s, but their origin can be traced back much further than that. The history of leggings goes back to 14th century Scotland, where men wore two-piece leggings (similar to chaps) for a casual look and military dress. It wasn’t until the 1960s that fashion leggings came about, when Joseph Shivers of DuPont created the first lycra leggings in 1959 with the intentions of women wearing them in both fashion and sportswear.

Over the past few decades, women and men alike have been seen wearing all types of leggings for exercise gear, casual ensemble and dressy attire. So why can’t you do the same? There are plenty of ways to style legging outfits for over 50, it’s all about figuring out what type of leggings work best for you and how to create an outfit that’s equally comfortable, chic, and classy.

Here’s how to wear leggings over 50:

Types of Leggings

What’s the best part about adding leggings to your wardrobe? There are so many different styles, colors, and patterns to choose from. Getting a better understanding of the types of leggings available to you can help you determine what will fit your style needs and exude the most comfort. Different types of leggings based on length include:

  • Ankle-length leggings
  • Mid-calf leggings
  • Footed leggings
  • Stirrup leggings

Different leggings fabric options include:

  • Leather or faux leather
  • Cotton
  • Polyester
  • Nylon
  • Jeggings, made from a denim-like material

Different designs of leggings include:

  • Ripped leggings
  • Basic color leggings
  • Printed leggings (such as floral, leopard, galaxy, tribal, glitter, etc.)

Most legging styles are designed with compression in mind. This is useful for someone with poor circulation, as compression leggings can help increase blood flow, and reduce soreness. For many, leggings are also designed to help contour the body - leggings can help hide cellulite in the butt, hips, thighs and abs, acting as a confidence booster no matter your age or body type.  

Wearing Leggings: Pros and Cons 

Once you’ve tried your first pair of leggings, you might have a hard time wearing any other type of pants again! Leggings are beneficial for women in so many different ways, but there are a few negative factors that might deter someone from wearing them on a regular basis. Here’s our list of pros and cons of wearing leggings over 50:



  • They’re comfortable. Leggings are designed with comfort in mind. No matter where you wear them, you’ll find freedom to move around instead of feeling restricted like you would in a pair of jeans. 
  • They’re great on their own. Leggings make a great pair of pants, giving you the opportunity to sport them around for looks and comfort.
  • They’re great with additional layers. Leggings can do just fine on their own, but you can also layer them with a skirt, dress, or pair of shorts. 
  • They’re great for any occasion. Whether you wear them during a workout or a night out on the town with your family, leggings are a great piece of clothing for any event. 
  • They can help you feel slimmer. Need a boost of confidence? Wearing leggings over 50 can help you look and feel your best. 


  • If you don’t wear them right, they could be unflattering. Most leggings are flattering, just so long as you wear the right pattern and color. Leggings in shades of white, gray or your natural skin tone can highlight imperfections and make you feel less confident when you wear them.
  • Not all materials are ideal for warmer weather. Leggings made out of certain materials are best for colder weather -however, leggings made out of cotton are breathable and great options for the warmer months! One of our brands, Jess and Jane, makes fantastic options for cotton leggings. 


    What to Wear With Leggings Over 50

    Want to learn how to wear leggings and boots over 50? Excited to try on a pair of leather leggings but you’re not sure where to start? We’ve got you covered. Below, we’ve detailed what to wear with leggings over 50 in regard to clothing items, shoes and other accessories to complete your look.

    Best Clothing Items to Wear With Leggings

    When it comes to picking clothing to pair with your leggings, length is important. Longer shirt will make your look more presentable and sophisticated.

    • An oversized sweater or sweatshirt
    • Long jackets
    • A wrap dress, short or long 
    • A blouse and blazer
    • A tunic

    Shoes and Accessories That Go With Leggings

    Just about anything goes with leggings. Use your personal style to guide you when picking the right accessories to go with your leggings and the rest of your outfit.

    • Leather boots
    • Sneakers
    • Flats
    • Heels
    • Cross body bag
    • Statement jewelry
    • Scarves

    Get Excited About Wearing Leggings Over 50 With Anthony’s Florida 

    Are you ready to purchase a pair of leggings but you’re not quite sure where to start? Anthony’s Florida has a variety of options to choose from that will get you excited about wearing leggings over 50. 

    A variety of colors, patterns, lengths and brands give you the opportunity to browse the online store and find the perfect pair to match your personal style. Once you’ve picked out one - or two - of your favorite pairs of leggings, you can browse the rest of the website to complete your outfit. We make it simple to find what to wear with leggings over 50 so you never have to worry about mismatching your ensemble.

    Shop our collection of leggings for women over 50 today!


    AnnnR Bayha

    Very informative. I appreciate any style help for over 50.

    Very informative. I appreciate any style help for over 50.


    Love the oversize look over leggings always. The breakdown on different styles/fabrics is great!

    Love the oversize look over leggings always. The breakdown on different styles/fabrics is great!

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