Leggings Are Back, And Here's How You Should Wear Them

A fashion expert’s tips for finding the right ones and styling them thoughtfully.
Shannon Mann

It’s been said that what goes around, comes around. The fact that leggings are making a return to fashion in a big way really brings that sentiment home.

If you (like me!) could excavate a few pairs from the back of your closet, resist the temptation to revive them. What’s changed? The fabrication, for starters. Thanks to better materials and better production, today’s leggings are of higher quality, befitting women of our age.

The trick is how to wear them.

Now, if you’ve been wearing leggings as your pant default for the last few years (no judgment), I’d like to gently remind you that the ones you’ve worn to your AM Pilates should be styled differently than the leggings you wear to, let’s say, meet a friend for lunch. When leggings are combined with the right extras, they can be worn for lots of occasions, from work to dinner out.

Here’s how.

Tips for the Best Legging Selection:

  • Find the right support: A great pair of leggings tucks you in all the right places. Look for sturdy waistbands that provide shape and support in your midsection and pass the “sit test.” While trying on leggings, I always sit on a chair or raise my knees a few times to tell me if the leggings will stay in place on my waist or if they will slip down/stretch out.
  • Material is key: Invest in a legging with a nice-looking, thicker material or even consider a knit or leather option if you want to ramp it up a bit.
  • Style details make the difference: Leggings with nice hemlines, well-appointed seams, and flare or straight leg shapes, all add some style oomph that elevates this fashion basic.

How to Style Leggings for the Day

For styling leggings in the daytime, I like to pair my leggings with a long, even oversized shirt or tunic, and, during the cooler months, pair the look with a shrunken vest as it reins in the volume on my petite frame and adds a bit of polish. My favorite shoe selections for daytime are a ballet flat, loafer, or a tall riding boot.

Leggings: Spanx ($78) or Commando ($108)

Shirt: Gap ($59.95) or Foxcroft ($79.49-$114)

Vest: Madewell ($88) or Eloquii ($89.95)

Shoes: Margaux ($225) or G.H. Bass ($175)

Makeup: Jones Road ($38)

Bracelets: Kate Spade ($48)

Glasses: Caddis ($99)

How to Style Leggings for Work

The key to executing the perfect work outfit with leggings is to create a style that’s sophisticated and polished. First, lean into layering—a blazer on top is perfect. Second, keep your look monochromatic, which reads modern. And last but not least, choose leggings that have elevated details like a proper waistband, finished hemlines, and style details like a down-the-front seam.

Leggings: Spanx ($98)

Shirt: Spanx ($84)

Blazer: Zara ($119)

Chunky Loafer: Franco Sarto ($99)

Earrings: Argento Vivo Sterling Silver ($12.98)

Bracelets: Anthropologie ($20)

Lipstick: Flyte70 ($32)

Purse: Kurt Geiger London ($129.97)

How to Style Leggings for a Night Out

This is the perfect opportunity to try leggings in a dressier fabric—leather, pleather, patent—and lean into a little glamor. I like pairing mine with a pretty blouse (sheer, metallic threading, lace). Personally, I love the look of a chunky pump, but you can also pair leggings with an embellished flat, a mule, or a suede-heeled bootie. Last but not least, have some fun with your jewelry—a bold hoop earring would be great.

Leggings: Good American ($120) or Commando ($118)

Lace Blouse: White House Black Market ($78) or Eloquii ($34.99)

Booties: Sam Edelman ($98.95) or DSW ($69.98)

Lipstick: Ilia ($28)

Rings: Ettika ($60)

Earrings: Kendra Scott ($75)

How to Style Leggings for Travel

Nothing beats the ease and comfort of leggings when it comes to a long flight, and they also make getting through security a breeze. The key is to avoid a shlumpy look and also choose pieces you’d happily wear once you reach your destination. Layers that have structure and solid, neutral colors should be your jam. Avoid coated leggings or pleather and go for breathable cotton blends.

Leggings: Old Navy ($34.99)

Denim Shirt: Banana Republic ($45) or Roaman’s ($47.99) or Frank & Eileen ($278)

T-Shirt: Sanctuary ($49)

Cardigan: Banana Republic ($72)

Sneakers: Sans Matin ($195) or Madewell ($88)

Glasses: Caddis ($99)

Necklace: Aureum ($177)

Shannon Mann

Shannon Mann is the face of Oysters to Pearls, a lifestyle blog inspiring women over 50 to be the best version of themselves. Not only does she share her love for fashion but also her love for health, beauty, and skincare tips. Shannon is a wife, mother, and breast cancer survivor.

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