Ripped Jeans Are “In” Again: Here’s How To Wear Them

Ripped Jeans

Ripped or distressed, these jeans are the best! We chose and styled five pairs of ripped jeans for any occasion.

To everything, turn turn turn, there is a season, turn, turn turn… and this season, that means exchanging your perfectly fresh, unadulterated jeans for a pair that look like they might have been mauled by a tiger, or at least worn during a couple of schoolyard dust-ups.

If ripped jeans aren’t your thing, we get it. Having a few small patches of skin exposed to the elements on a cold and windy winter day isn’t for everyone. That said, we’ve done some recon work on the ripped jeans market for fall and winter, and we’ve got to say, we’re impressed. We’ve also come up with a few little tricks to keep your legs warm, holes and all.

Now we know what you’re thinking: I’m going to buy a pair of these jeans and they’re just going to sit in my closet, unworn, and I’m going to be wishing I put that cash towards my Caribbean cruise fund. Well if the past year has taught us anything, it’s to be wary of cruises — and that when it comes to fashion, everyone just wants to be comfortable. The ripped jean provides you with some extra give in all the right places, and can even add a bit of unexpected sexiness to an otherwise very conservative outfit. Plus, honestly, distressed jeans just look really cool, like wearing big dark sunglasses, or successfully tossing a crumpled up piece of paper into a trash can that’s 10 feet away. Or driving a sports car, as long as it’s not during the throes of a mid-life crisis.

That’s why we implore you to trust us when we say: Give ripped jeans a try. If your concern is that you don’t know how to wear them, we’ve got your back, as usual. We’ve created five looks for five different occasions that will make you wonder why you ever stopped wearing ripped jeans in the first place.  

Go for Grunge

We don’t know if you’ve noticed, but the ‘90s are back, and that means it’s ok to dress full-on Kurt Cobain in a graying white undershirt and an oversized flannel. We don’t recommend that you stop washing your clothes, but going a little Kurt can’t hurt. Here’s how to wear it:

The Jeans: Signature by Levi Strauss & Co. Juniors’ Ultra High Rise ’90s Straight Fit Jeans

'90s Jeans

Nothing says grunge like a pair of light-wash, slightly destroyed jeans. We love these, because the fit is the exact kind that’ll make your bum look sky-high.

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The Belt: J Crew Classic Belt

J Crew Belt

The only downside of the ‘90s jean, which generally has virtually no give, is that they stretch during the day. Keep your pants from saggin’ (and your waist looking cinched) with a simple black belt. You’ll get more wears out of this one from J. Crew than you’ll know when to do with.  

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The Undershirt: The Pima Micro-Rib Tank from Everlane

Black Tank

There are two essential directions you can go from here, tops-wise: full Cobain with a plain ‘ole Fruit of the Loom white tee, or a bit more Courtney Love with a black tank. We choose the latter. This ribbed one from Everlane will probably outlive the combat boots you’ve had since the ‘90s.

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The Flannel: Women’s Scotch Plaid Flannel Shirt


The ‘90s called… and they said that L.L. Bean will never not be cool. The Bean tends to run a little bit large already (bless them) but we suggest sizing up to make sure you get the quintessential nice, oversized look.

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The Shoes: Dr. Martens Chelsea Boot

Doc Martens

The doctor is in — Doc Marten, that is. We wouldn’t be so cruel as to subject you to the original shiny, lace-up version, but these are actually cute and versatile. And they’ll still make you feel like you’re stickin’ it to the man.

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Be the Boss

While we don’t necessarily condone wearing ripped jeans in a business setting, if your office has a relaxed dress policy or you’re going out with coworkers and don’t want to look too stuffy, ripped jeans can actually be part of a very put-together look.

The Jeans: Levi’s 501® High-Rise Distressed Skinny Jeans in “darkside of the moon”

Dark Jeans

These jeans are great because they’re not light enough to be overly casual, but the gray color is unique and doesn’t seem like it’s a jean for going clubbing. They’re just distressed enough to be cool, without being inappropriately informal in the office.

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The Shirt: Relaxed-fit garment-dyed lightweight cotton poplin shirt

White Button Down

Overcompensate for slightly less-formal pants with a crisp, classic white button. This one will never go out of style.

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The Blazer: Capsule 121 Hailey Triple Pocket Jacket

Black Blazer

A solid black blazer is probably one of the best staple wardrobe pieces you can invest in. We think this fitted option is polished and professional, even though the material still has lots of softness and give.

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The Coat: Daphne topcoat in Italian boiled wool

camel jacket

A great way to keep your legs warm in distressed jeans is to wear a long coat. This classic topcoat from J. Crew will be your new go-to jacket for the season, and will make you look like a million bucks (and then some).

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The Shoes: Kelly and Katie Misha Pump

Black pumps

This is a pump that’s not too tall, not too short- it’s just right. You’ll be able to wear them all day without worrying about blisters.

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Take Them Out on the Town

One of the other first things that should come to mind when you think of ripped jeans is “sexy.” It’s an easy way to show a little bit of skin without being too scandalous, even though that does mean shaving your legs in the winter. (If you want to, that is.) For maximum sultriness, it’s all about getting the right fit, making sure the rips are in the proper places, and pairing them with the ideal shoes and top.

The Jeans: Spanx Vintage Distressed Ankle Skinny Jeans

black spanx

Spanx are bestsellers for a reason— they’re made to look amazing on absolutely everyone. These jeans are chock full of tummy-tucking elastic, and will make you feel sexy as heck.

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The Top: Sleek Twist Blouse in Lime

green top

With an all-black outfit, we love one big, statement-making pop of color. This top should do the trick.

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The Coat: Up on a Tuesday Black Vegan Leather Jacket

leather jacket

If you’re ethically or financially opposed to buying a leather coat, vegan leather is a game-changer. This classic leather jacket will keep you feeling warm while you bar-hop with your buds.

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The Boots: Harlie Over the Knee Boot

over the knee boot

Tip two for keeping your calves from getting cold in ripped or distressed jeans: Try an over-the-knee boot. This pair screams sexy, and will make you feel like you’re wearing a second pair of pants.

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Keep it Casual

Ripped jeans can be the perfect bottoms for a freewheeling activity that might require getting a little dirty, but isn’t so active that you’re going to be profusely sweating. Think gardening, biking, even taking your kids or grandkids on a trip to the playground: activities where skin-tight jeans would be too constricting, but you don’t want to be caught wearing sweatpants (again).

The Jeans: 7 for All Mankind Alexa Cropped Jeans in Lovechild

Seven Jeans

If you’re not ready to commit to a fully ripped jean, this casual pair is the perfect in-between— it’s got distressed bottoms which are great for a low-commitment outing.

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The Quarter-zip: Women’s Quilted Quarter-Zip Pullover

Quarter zip

Preppier folks will absolutely live in this quarter-zip. It’s adorable, it’s toasty, and cute as a button. (We want it in every color.)

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The Jacket: Classic Plaid Jacket


Plaid jackets are having a HUGE moment, and this one from Anthropologie tops our list. It’s short so you won’t feel like you’re being swallowed by it, and it’s easy to tie around your waist if you get hot during the day.

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The Shoes: Women’s classic bean boots

bean boots

The most versatile shoe of all time is the classic Bean boot. If you don’t already have a pair, buy one now — you’ll be able to pass them down to your grandkids.

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Buy Into the “Boyfriend” Look

Though we think the term “boyfriend” is a little silly — since it’s now being used to describe any jean that’s not totally form-fitting — we do love how all of the pieces below fit together. This is the type of ultra-comfortable outfit you can throw on and wear basically anywhere, and still look put-together.

The Jeans: Joe’s Jeans “The Scout” in white

white jeans

These distressed white jeans are loose, comfy, and versatile enough to transition well into the winter, if you want them to.

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The Button-Down: Classic-fit cozy gauze shirt in topiary

green shirt

We love a staple button-down that’s thinner and not too stiff (perfect for layering), and this one fits the bill. The moss green is our personal favorite.

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The Vest: Women’s L.L.Bean Sweater Fleece Long Vest

white vest

If you’re going for white on the bottom, why not go all in? This fleece vest is the perfect fall piece, and the color will have people questioning why we ever made up that “no white after Labor Day” rule in the first place.

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The Belt: Perfect leather belt

brown belt

Nothing pulls an outfit together like a brown leather belt. This is one you can wear with most outfits in your wardrobe.

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The Shoes: Blundstone Classic 550 Chelsea Boot

brown boots

We know Blundstones are pricey, but they will last you forever and a day. Plus, they’re unisex, waterproof, durable, easy to slip on and off, and can be worn with just about any pants in your wardrobe.

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