This is Ask the Experts: Where our favorite fashion know-it-alls share their wisdom. Just because you can trust your style instincts doesn't mean you should have to.

By Samantha Sutton
May 14, 2020 @ 10:30 am
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Remember when we, as a society, came together to declare that leggings are not — and we repeat, not — pants? What the heck was that about? It was like we were trying to deny ourselves one of the tiniest joys in life, aka comfort, by establishing some made-up rule that states full-coverage bottoms are somehow unacceptable to wear in public.

Anyway, we're sorry (and yes, we're mostly apologizing to ourselves). Leggings are pants, and they can be worn in public. Victoria Beckham has done it, Ashley Graham has done it, and nearly every day, we spot another celebrity pulling off this look, giving us ideas for how to rock our own black, gray, and leopard-printed pairs.

And then, there are the people who dress the celebrities: the stylists who pull together winning red carpet looks, or come up with a street style combo we think about for years. They've given leggings a thumbs up, too, and have a variety of tips for making them look like a million bucks.

So, how does one get away with wearing leggings (almost) anywhere? And which styles are worth purchasing, ASAP? We asked and eight stylists delivered, ahead.

1. Sarah Slutsky

Has Worked With:

Maya Hawke, Emma Watson, Elizabeth Olsen, and Cynthia Erivo.

Favorite Leggings Brand:

I love Cuyana and De Rococo for ‘dressy leggings,’ Alo and Outdoor Voices for active.

How She’d Style ‘Em:

I have found myself in leggings as a form of motivating myself and reminding myself to exercise every day. When I do have to go to the farm to pick up our groceries, I have been loving the Demi ballet flats from Margaux, thick cozy socks pulled up high with a Freda Salvador lug sole boot, or my classic white and black logo Vejas.

2. Erica Cloud

 

Has Worked With:

Kacey Musgraves, Awkwafina, D'arcy Carden, and Zooey Deschanel.

Favorite Leggings Brand:

I do love Everlane's Perform leggings, [but usually] I go for sweats or joggers over leggings. I like the fabric being baggy or slinky instead of tight, and find it helps balance whatever type of top you choose. I love Dame's Luxe sweatsuit, Entireworld’s men's sweatsuits, Monrow's vintage jogger.

How She’d Style ‘Em:

As someone that wore jeans pretty much daily before [tge coronavirus], it was quite a transition. I love pairing a lounge pant with a cozy La Ligne sweater or x Karla tee or sweatshirt. Wearing an oversized button-down with leggings is incredibly classic and effortless. I just got a pair of cream Vince Branine ballet flats that are super chic and feel like a slipper. I'm also a huge fan of a loafer with literally anything. 

3. Andrew Gelwicks

Has Worked With:

Catherine O'Hara, Delilah Belle Hamlin, Ryan Jamaal Swain, and Ava Michelle.

Favorite Leggings Brand:

Calzedonia and Commando make some of my favorite leggings. They combine functionality, comfort, and style. 

How He’d Style ‘Em:

If braving a pair of tights as pants, the best way to style them is with a heel. Either a sleek pump or wrap-up sandal — use something to elevate the look. For the top, I would suggest something that is not athleisure. Instead of an oversized hoodie, try on your boyfriend's button-down shirt, buttoned up, or a black blazer. 

4. Taylor McNeill

 

Has Worked With:

Marc Jacobs, Bobbi Brown, Covergirl, Lemlem by Liya Kebede, Theory, and Vera Wang.

Favorite Leggings Brand:

I’m super excited to see the new sustainable activewear line CERES by Nina Miner and Kumi Sawyers dropping soon. I want to live in the whole collection!

How She’d Style ‘Em:

To be honest, I'm not a legging girl. I prefer track pants. Dress them up for day with a classic men's button-down — I love my boyfriend's old Comme shirts and collect vintage Brooks Brothers. Layer over a good tee, throw on a trench or a statement coat with a sneaker and you're good to go! 

5. Courtney Mays

 

Has Worked With:

NBA players Chris Paul, Blake Griffin, and Kevin Love.

Favorite Leggings Brand:

I prefer a high-rise legging that sucks in the tummy a bit. Not Spanx tight (I still want to breath as I run my errands) but a smoothing tuck-in. Also, leggings must be thick — no one wants to see your panties or lack thereof when the light catches you. And finally, nothing is worse than constantly having to pull up your leggings, so finding the right rise and length is key. I love a classic Nike legging, but also I just discovered Beyond Yoga and Good American. They have a huge size range, which makes this plus-size girl a happy camper. 

How She’d Style ‘Em:

Pair with a white tee and an oversized blazer; wear an oversized menswear shirt as a tunic with a loafer or white sneaker; grab your worn-in oversized band tee, layer with a Moto or oversized denim jacket; wear a long trench coat and combat boots. Long…oversized…see, there is a theme here. I love a legging when you can see a little ankle, or when the shoe is a bit chunkier to balance the skin tight pants. My go-to shoes are Nike Air Force (only white), Amiri double-buckle combat boots [Farfetch.com, $1,290], and a flat mule. I bought a million pair of pointed slides (Celine has a pair now) in Marrakesh last summer and plan to wear them with every pant option until I can't wear them anymore!

6. Lo VonRumpf

 

Has Worked With:

Meg Donnelly, Sarah Jeffrey, Lucy Hale, and Hayley Orrantia.

Favorite Leggings Brand:

My favorite faux leather leggings are from SPANX. They are high-waisted, comfy, and look amazing on. I also love the leggings from Aritzia. They have bold colors and patterns to spice up my client’s wardrobes and looks. 

How He’d Style ‘Em:

Leggings are a staple, and are now better designed so you can have a good selection with (flattering) fabrics, prints, lengths, and colors. I love a faux leather legging paired with an oversized men’s blazer, over a crop top or simple tee. You can be versatile in dressing up (or down) your look by changing out the crop top for a sweater. I also love styling bold-colored leggings with a neutral A-line skirt and a cardigan for a stylish work look. 

Comfortable shoes are a must-have, so I like to finish off these looks with a patent leather kitten heel or a white sneaker. A ballet flat looks great, too. 

7. Kirsty Stewart

Has Worked With:

Patricia Manfield, Rochelle Humes, and Anna Friel.

Favorite Leggings Brand:

I really enjoy the leggings from Wardrobe NYC and Sporty & Rich. They are my go-to for wardrobe staples.

How She’d Style ‘Em:

One way to elevate your look is to pair leggings with knee-high boots and an oversized sweater; or perhaps a tank top, oversized leather blazer and biker boots. For summer, I expect to see colorful leggings make an appearance. We have seen them from brands such as Mugler, Maisie Wilen, and Marine Serre, and they were a hit during Copenhagen Fashion Week. For the past year or so, neutrals have dominated our Instagram feeds, but it’s time to move into more sugary tones and this is a great way to make the transition.

You could also opt for a pedal pusher opposed to a full-length legging. It’s a trend we saw a lot of at the back end of 2019 since they were shown on the runways of Khaite, Jacquemus, Maryam Nassir Zadeh in 2018. For an extra ‘90s feel, wear with a cute cropped cardigan, low heels, and baguette bag.

8. Christina Pacelli

 

Has Worked With:

Laverne Cox, Nina Dobrev, Britney Young, and Danielle Brooks.

Favorite Leggings Brand:

I love the faux leather leggings from Commando because they look like leather but are much lighter weight. My favorite athleisure leggings brand is PE Nation.

How She’d Style ‘Em:

I love styling leggings under a skirt, an oversized sweatshirt, and a crop top (a crop top with high waisted leggings only!!). I also love styling them with sock booties.