How to Wear Leggings: The Ultimate Guide


Most people think of fashion as fun and fluffy and not overly controversial. Until the talk turns to leggings. Suddenly, sides are taken and friendships are lost. As in lifelong friendships. Over a few ounces of cotton jersey.

Don’t let this happen to you. Before you enter into the legging wars, it’s important to be prepared. And, sadly, you’re going to have to take sides.

Are you in the “wouldn’t be caught dead in leggings” camp or the “couldn’t live without them” camp?

The “LuLaRoe forever” camp or the “LuLaRoe killed fashion” camp?

The “leggings ain’t pants” camp or the “oh yes they are” camp?

And, although I am staunchly pro-legging (except when I’m not),  like the good fashion editor that I am, I see both sides of the story.*

Let’s get real here. Leggings aren’t going anywhere. They have now reached staple status, and even the most ardent legging-loathers can be spotted wearing something suspiciously similar to leggings—the skinny pant. So with all this focus on sleek, stretchy bottoms, it helps to know how to wear them. And for those of you who’ve never met a LuLa pattern you liked, no worries. Solid colors are, without a doubt, the chicest and most versatile way to wear leggings.

(Reminder: Pics in my posts are linked, so just click on the pictures to shop.)

Here, how to pull off leggings, for every body:

Pick a Color

Just kidding. There is no picking a color. There is black. Only black. Okay, predominantly black. If you want to push the limits of legging-dom and really let out your wild side, you may also consider grey, navy, or a dark denim blue. Under no circumstances, unless we are talking about yoga-wear, or unless you are a child, should leggings be red, hot pink, or anything else resembling a color and/or crazy print. A subtle print or texture is acceptable, but if you’re on the fence, remember this rule. There is black. Only black.

(I’m currently spearheading legislation to outlaw white and nude leggings. Stay tuned to learn how you can get involved in this important issue.)

Make Them Flattering

Believe it or not, this is easier than it sounds. A thicker, more substantial fabric will always be more flattering, unless (isn’t there always an exception?) the fabric is chunky and textured and adds bulk (sweater knit leggings, for example). Lightweight leggings can be comfortable but generally don’t offer much support or control. And this brings me to the next point: control top leggings or leggings with a definite waistband are great for streamlining the tummy and waistline. Spanx, Yummie, and Commando all make versions of these.

Full length leggings are generally the most versatile and work with flats, tall boots, heels, and wedges (image on the right). Cropped leggings are best worn with ankle booties, but can also be worn with flats and sneakers. Make sure to leave a little leg exposed between the hem and the top of the boot (see image on the left)!

leggings 2 ways

Finally, CYB, ladies. Cover Your Bum. Unless your leggings fall into the third category, below (leggings that are actually pants), you need to find a top that is long enough to provide coverage in the front and the back. The front can be just barely covered, with a slightly longer back, but they should both be covered.

leggings 4 tops

In the illustration above, the first image shows a tight (and short) shirt worn with leggings. Leggings look best when they are balanced out with a bit of volume, so go for a top that’s a little looser. The second image shows a top that is higher in the front, which doesn’t give you the front coverage that you need. The third top is closer, but still a little too short. Finally, the fourth top is a true tunic, providing enough coverage in the front and the back.

Lastly, make sure that the hem of your tunic doesn’t end at an unflattering spot. A hem that cuts straight across the widest part of your hips or bum will make them look wider. This is fine if you need a little more amplification in those areas; not so much if you already have generous curves. Go a bit higher, or, better yet, lower, for maximum flattery!

Find the Right Pair

From the super casual look of a simple cotton knit legging to dressier styles in heavier knits with chic detailing, there’s a legging for every setting. The dressier styles are every bit as comfortable as your old standby, and a lot more versatile. Dress them up for a night out or for work, and then throw on a graphic tee and sneakers for the weekend!

  1. Casual Cotton Knit Leggings

    These comfy basics ar strictly for lounging, exercising, or other very casual settings. These are not work leggings or night on the town leggings. Think of them as an alternative to sweatpants.

Black high waist ankle length leggings from Topshop, $20, work great for most casual purposes.

2. Leggings with Benefits

These leggings have seams, sleek panels, actual waistbands and other details that make them far more versatile than your standard cotton knit workout leggings.

Kit & Ace Pencil Me In Leggings, $118,

Main Image - Two by Vince Camuto Faux Leather Trim Moto Leggings

Two by Vince Camuto Faux Leather Trim Moto Leggings, $79, Nordstrom

Main Image - SPANX® Look at Me Now' Seamless Leggings

SPANX® Look at Me Now’ Seamless Leggings, $68, Nordstrom

3. Leggings Posing as Pants

Okay, these really are pants, y’all. For real. These have the stretch and comfort of leggings, but the details and style you associate with pants. And the versatility. Some are called pants, and some are called leggings, but they are essentially a hybrid. And, because they are both, you can wear them with shorter tops or with tops tucked in, a la pants, or under a tunic or a dress, like leggings.

Primary Image of Ponte Skinny Pants

Ponte Skinny Pants, $59.99 (sale), Ann Taylor

Main Image - rag & bone/JEAN Ripped Denim Leggings

rag & bone/JEAN Ripped Denim Leggings, $225, Nordstrom

Black low rise extreme stretch jean legging, $79.90, Express

4. Leather Leggings

Okay, these are the most underrated wardrobe staples of all time. I have had the same Gianni Bini pair for years, and this season I am finally looking for a replacement. They make any tunic you pair them with chic-er, edgier and hipper. Basically, all the cool adjectives not typically associated with leggings. I prefer the faux leather kind because they’re stretchy and comfy and, most importantly, machine washable. Also, they’re far more affordable. If you don’t feel bold enough to wear these with tunics, try them underneath dresses or with long slouchy sweaters.

Main Image - BP. Faux Leather Leggings

BP Faux Leather Leggings, $17.40, Nordstrom (a great choice for tall girls!)

Main Image - SPANX® Faux Leather Leggings

SPANX® Faux Leather Leggings, $98, Nordstrom

J. Crew stretch leather leggings, $495,

Choose a Great Top

There are tops designed especially for leggings. They are called tunics. If you are short-waisted, like me, non-tunic tops can sometimes be long enough to double as tunics. If you’re longer waisted, then you’ll have to find yourself an actual tunic. Fortunately, that’s not hard. Here, a few great tunics, by body type:

Style Dial® 1

As always, go with a vertical neckline, when possible, and a consistent pattern. Simple lines and minimal fuss help to maintain the proportion in your body.

Vince Camuto long sleeve windowpane v-neck tunic, $99, Dillard’s

Style Dial® 1 (3)

Look for a vertical neckline and some detail at the middle to define your waistline.

Back Road Ramble Tunic, $44.99, ModCloth

Style Dial® 2

Your ideal tunic should have a horizontal neckline (scoop, boat neck) and a straight hem. Bonus points for an empire waist and embellishments or details on the top third of the tunic.

Eileen Fisher Scoop Neck Tunic

Eileen Fisher scoopneck tunic, $138, Belk

Style Dial® 2 (3)

Your best tunic features a round or horizontal neckline and waist definition.

Genuine Ingenuity sleeveless top, $34.99 (sale), ModCloth

Style Dial® 3

Movement, detail and even volume can all be very flattering for building out your shape and creating curves. A vertical neckline is usually best, but a horizontal one will also work provided your shoulders aren’t broader than your hips. Just add a long necklace! The pleats and asymmetrical hem create the illusion of shape.

CATHERINE Catherine Malandrino Hazel Pleated Asymmetrical Sleeveless Tunic

CATHERINE Catherine Malandrino Hazel Pleated Asymmetrical Sleeveless Tunic, $98, Dillard’s

Wear Them Everywhere

When chosen well and styled properly, leggings are now considered appropriate for all but the most conservative settings. Here, how to pull leggings off for five different settings, and five different body types.

Leggings for Work

Thick, ponte leggings or pant-leggings work great for work when worn with a dressy blouse tunic (the one below is shown tucked, but should be untucked with leggings), a jacket (a gorgeous color is an unexpected touch) and classic accessories. The v-neck tunic and classic blazer with a triangle opening at the hem makes this a Style Dial 1-friendly look.


2. Leggings for Play

Leggings, a knit top or cardigan, a scarf and a pair of boots is a combination that turns up in countless Pinterest looks, for good reason. It’s chic, comfy and flattering. I chose a chambray top that can be worn slightly unbuttoned, a long cardigan (worn open to create a flattering line for a Style Dial 1 (3) ), moto boots, a sleek tote and a fun scarf.


3. Leggings for Date Night

The strong horizontal lines of this trendy top is very Style Dial 2-friendly, as is the shorter pendant necklace. Sleek leather leggings, a red clutch and glam heeled boots make this a great date night look.


4. Leggings for a Girls’ Night Out

A Style Dial 2 (3) would be gorgeous for a girls’ night out with this swingy blue tunic and clutch worn with sleek leggings (notice the leather details) and strappy heels.


5. Leggings for Laid Back Days

Take leggings back to their athletic roots with this sporty look for a Style Dial 3. The zippered detail at the hips of the leggings and the ruched tee are both great picks for this body type, as is the swingy hem cardigan.


Leggings are here to stay, so I hope that these ideas have helped you feel comfortable embracing them. Everyone knows they’re comfortable, but these looks prove that they are also versatile, flattering, and most of all, chic.

*Opinions in this post are subject to change without notice (wink).



  1. Linda A Meyers says

    I wear all colors of leggings for work and play. They make me feel good and make me happy.

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