5 Ways to Revamp Your Skinny Jeans

Conflicting reports arose for 2020 about the relevance of a certain closet staple — skinny jeans. Some fashion experts vote “in” because of their universally flattering versatility. Others, such as Bobby Schuessler of WhoWhatWear, explained that skinny jeans should stay in the back of your closet to make way for nostalgic styles like flares coming into the forefront.

We wanted to set the record straight and in doing so, saw great points on both sides of the argument. We came to the conclusion that skinny jeans can never truly be “out,” sometimes they just need a refresher. To further highlight our point of view, we paired some of our favorite skinny jean styles with Fall/Winter 2020 trends, courtesy of local boutiques.

Cool and Casual

Sage Oversized Coat, $110. BB Dakota Sweater, $64, Vervet Jeans, $64. Available at Hailee Grace Boutique. Ora Et Labora Large Bead Necklace, $85. Available online and at Modern Nomad. Converse High Tops, Stylist’s Own. Hair Accessories, worn throughout, $10. Available at Vida Salon Cherry Creek.

 Close up of Cool and Casual Look

The Lowdown: This winter, the bigger the coat, the better. An oversized jacket balanced out the skinny silhouette of these jeans, while the distressing and throwback high tops brought a bit of edginess to the overall outfit. A mix of textures and pops of red and pink — one of our favorite combinations for the holiday season — amped up this look and made it new and fresh.


Rebellelion Denim Jacket
Denim Jacket, Price Upon Request. Available at Rebellelion. Vervet Jeans, $62, Handbag, $40. Available at Hailee Grace Boutique. Boots, Stylist’s Own.

Close up of purse and shoesRebellelion Denim Jacket

The Lowdown: Texas Tuxedo, Canadian Tuxedo, whatever you call it, denim-on-denim isn’t going anywhere. In order to make the look more fashion and less “Farm & Fleet,” the key is to pair different washes together and. To kick it up even further, add some cool patches like this custom jacket from Rebellelion. Pair this denim-on-denim look with sneakers, or add a bright pointed-toe boot and a lady-like purse to take it from day to night.

Close up of Rebellelion Denim Jacket


Japanese Kimono, $82, Ora Et Labora “Bomba” Boots, $585. Available online and at Modern Nomad. Frayed Jeans, $65, Daydreamer Pink Floyd Tee, $60. Available at Hailee Grace Boutique.

The Lowdown: Style trends from the ’70s are making their way back around, popping up on runways from New York to Paris. To put a skinny jean-spin on a ’70s look, pair fringe-hemmed denim with a psychedelic graphic tee, statement boot and patterned overcoat. Bring this look into 2020 using a technique called “pattern stacking” — the combination of textures, prints and patterns — all within the same color family.

Statement Skinny

Sock Booties, Blazer and Zara Top, Stylist’s Own. Amy Lisojo Amy Lisojo Tiger Stripe Jeans, Price Upon Request. Pearl “Momo” Bag, $170. Available at Modern Nomad.

The Lowdown: Colored denim is “all the rage,” and pairing it with a feather-trimmed blazer checks a few different fall/winter trend boxes. To balance out the funky vibe of the skinnies, a buttoned-up bow blouse and a very feminine purse added even contrast and pulled this look together by making it more wearable.

Date Night Romantic

Rome Jacket, $285, Isla Cami, $88, Palm Clutch, $28. Available online at GLENN + GLENN. Just Black Denim Jeans, $68. Available at Hailee Grace Boutique. Public Desire Faux Snakeskin Boots, $30. Available online.

The Lowdown: Skinny jeans are the perfect option for date night. They’re comfortable — make sure you get some with stretch, like the ones found at Hailee Grace — and allow you to be ready for wherever the night takes you. To style, add a silky tank and a wool jacket to incorporate some texture and elevate the jeans to make them date-night ready. Faux snakeskin boots — on trend for the winter — added a punch to this classic outfit. Find ankle-height boots with a wider shaft to make it easy to tuck in skinny jeans.

Photographed by Amanda Piela.

Model Paris Creed (Goldie Mae Productions). 

Hair by Vanessa Whitmarsh.

Makeup by Liana Conway

Clothing and accessories provided by Hailee Grace Boutique, Modern Nomad, Ora Et Labora, GLENN + GLENN, Rebellelion Co., Public Desire and Amy Lisojo.

 Styling by Cheyenne Dickerson and Jordan Laudadio

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