Here’s How to Wear (and Not Wear) Your Skinny Jeans in 2020

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Published Oct 24, 2019

When skinny jeans first entered the fashion scene, I thought: These are cool and we’ll probably just wear them for the next few months before moving on. Boy, was I wrong. It’s been almost 15 years since slim-fit jeans became a universal go-to and, surprisingly, it doesn’t look like they’re going anywhere anytime soon.

It’s likely, then, that you have a stack of these babies sitting in a drawer right now, and you’re wondering what on earth you can wear them with to avoid looking like you crawled out of a mall from 2010.

I have just one tip for you: Think about your footwear.

Here, four skinny jean and shoe combos that are definitely au courant and three looks that you should retire—for good.

woman wearing skinny jeans and combat boots

Christian Vierig/Getty Images

Yes: Cropped + Combat Boots

There’s a reason why skinny jeans are an off-duty model favorite: They’re just so damn easy to throw on. They also pair well with flat boots, like the combat style pictured here. Cropped floodwaters feel much more modern than a pair of skinnies that are three inches too long, so call your tailor or grab a pair of scissors and go for the frayed edge look. Bonus: You do not have to be a size zero to make this outfit work. It truly looks great on all shapes and sizes.

Get the look: Levi’s jeans ($98); Agolde jeans ($158); Schutz combat boots ($245); Paul Green combat boots ($529); Jimmy Choo combat boots ($1,295)

woman wearing skinny jeans and tall boots

Christian Vierig/Getty Images

Yes: Light Wash + Knee-high Boots

As a fashion editor, my favorite part about skinny jeans is that they’re like the blank canvas of denim. I.e.,: You can wear them with (almost) any style of shoes. My pick for this year is to tuck a light-wash skinny into a sumptuous heeled boot—your pick if it’s suede or leather. You might notice that the pair pictured above are looser than your average jegging. That’s because a trendier take on the style does, indeed, allow your leg to enjoy some breathing room.

Get the look: DL1961 x Marianna Hewitt jeans ($179); Re/Done jeans ($258); Saint Laurent jeans ($690); Sam Edelman boots ($180); Vagabond boots ($240); Tamara Mellon boots ($795)

woman wearing skinny jeans with white sneakers

Edward Berthelot/Getty Images

Yes: Frayed Edge + Sneakers

Let your trendy comfy sneakers steal the spotlight by pairing them with a pair of ankle-framing skinny jeans and go ahead with a frayed hem, if that’s what you like. The slight distressed detail adds just the right amount of texture to take things a step above basic.

Get the look: Wit & Wisdom jeans ($78); Rag & Bone jeans ($137); Lover + Friends jeans ($168); Nike sneakers ($75); Asics sneakers ($130); Balenciaga sneakers ($995)

woman wearing skinny jeans and black boots

Christian Vierig/Getty Images

Yes: Faded Black Jeans + Black Boots

The pairing of black on black gives the illusion of endless legs, almost as if you can’t tell where your pants end and your boots start. So, if you’re looking to go leggy, shoot your shot. I love this look right now with a black bootie that boasts a walkable stiletto heel. Sure, it errs on the side of classic rather than trend-focused, but there’s nothing wrong with that.

Get the look: Levi’s jeans ($50); Madewell jeans ($135); GRLFRND jeans ($228); Everlane boots ($225); Miista boots ($435); Jimmy Choo boots ($950)

woman wearing skinny jeans and a crop top

OGUT/Star Max/GC Images

Skip This: Dark Ripped Denim + Light Boots

This look reads immature—like you’re headed to a kegger—and while the pointy boots are on-trend, their stark contrast only serves to shorten your legs. Pair them with a boyfriend or relaxed jean for a more contemporary look.

woman wearing skinny jeans and white button down

Jacopo Raule/GC Images

Skip This: Super Faded + Printed Mules

Blue jeans that are so faded they almost appear white are such a relic from the early 2000s. And when you match them with loud, printed mules, you get a mashup of eras that feels like time travel gone wrong. Long story short, it’s best to keep those ultra-light jeans in the past.

woman wearing a red sweatshirt and skinny jeans

Raymond Hall/GC Images

Skip This: True Blue + Ballet Flats

If your exact outfit was once worn by Lauren Conrad on The Hills, there’s a pretty good chance it’s outdated. Plus, ballet flats aren’t even that great for your feet. Still, this outfit combination isn’t a total bust. Simply upgrade to a sleek pair of penny loafers and swap your extra-faded blues for a more pigmented shade—then you’ll be ready to usher in 2020 in style.