Scroll To See More Images

Jeans are arguably the most versatile and long-lasting item in any wardrobe. They come in myriad different hues, shapes, sizes, styles—you name it. And while it’s easy to pair your favorite denim with a graphic tee for a casual look, figuring out how to dress up jeans in order to make them perfect for any occasion takes a little bit more creativity.

Luckily, there are so many street style mavens, fashion bloggers and influencers who have cracked the code for us. During our occasional lack of sartorial imagination, we can turn to these fashionistas and let them inspire us with their effortlessly cool and classic ensembles. Thanks, guys!

To give us all a bit of inspiration, we rounded up a bunch of different ways to dress up all your favorite pairs of jeansFrom elevating boyfriend jeans to create the perfect office-ready ensemble to taking boyfriend jeans from day to night, there is no shortage of ways to make your denim look chic. No matter your favorite style of jeans, there’s a way to make them look as polished as you want. Using simple tricks like adding a blazer and heels or pairing a graphic tee with a more polished jacket, these stylish folks can amp up any pair of denim.

Don’t be afraid to go bold, try something new and switch it up. You might find that the top you pushed to the back of your closet looks amazing with your high-rise flare jeans. The possibilities are truly endless, but we rounded up 10 different looks for you to try out below. Go forth and wear those jeans in whatever way you want. Read on to see all of the cute outfits. 

STYLECASTER | How To Dress Up Jeans

iMaxTree.

With a Long Cardigan.

This long cardigan look is comfortable and chic. If you’re headed somewhere fun, like a bar, layer an open cardigan over a bralette (like is shown above) or if you’re headed to the office, simply switch it out for a simple tank.

STYLECASTER | How to Dress Up Jeans

Courtesy of L’AGENCE.

Galena Cardigan

This subtly striped cardigan by L’AGENCE is perfect for dressing up your jeans.

STYLECASTER | How to Dress Up Jeans

Courtesy of Citizens of Humanity.

Annina Trouser

Tailored jeans with a slight flare will compliment the silhouette of a long cardigan nicely.

STYLECASTER | How To Dress Up Jeans

iMaxTree.

With an Oversized Blazer.

When in doubt, blazer it out! An oversized blazer is a fail-proof way to look put together. I love shopping for them in the men’s section of secondhand stores but Zara always works too.

STYLECASTER | How to Dress Up Jeans

Courtesy of Zara.

Oversized Striped Blazer

A striped blazer incorporates a basic patterned element into your outfit without making it look loud.

STYLECASTER | How to Dress Up Jeans

Courtesy of Free People.

Marx Slouchy Cargo

This pair of cargo pants are ultra soft so you’ll be cute and comfortable.

 

STYLECASTER | How To Dress Up Jeans

iMaxTree.

With an Off-The-Shoulder Knit

While a classic sweater always is a good pick to wear with jeans, picking an off-the-shoulder knit top makes the look a little flirtier. This style works well in either a neutral tone or a solid bright color.

STYLECASTER | How to Dress Up Jeans

Courtesy of Remi x Revolve.

Lindsay Off Shoulder Sweater

This white off-the-shoulder sweater was made to wear with jeans and is available in sizes XXS-4X.

STYLECASTER | How to Dress Up Jeans

Courtesy of Good American.

Good Skate Jeans

I love how the knit is paired with baggy jeans in the street-style photo. This pair from Good American has the right amount of slouch.

 

STYLECASTER | How To Dress Up Jeans

iMaxTree.

 

With Statement Stripes.

The French fashion girls are pros at dressing up jeans and one of their go-tos is a striped sweater, button-down or long sleeve.

STYLECASTER | How to Dress Up Jeans

Courtesy of Zara.

Striped Knit Sweater

This striped sweater works all year round—wear on a boat over the summer for a nautical look or with boots in the city for a Parisian look.

STYLECASTER | How to Dress Up Jeans

Courtesy of Mother.

Rambler Zip Ankle

Slightly cropped jeans give you the opportunity to show off a great pair of boots or kitten heels.

 

STYLECASTER | How To Dress Up Jeans

iMaxTree.

 

With More Denim.

Canadian tuxedos are always in style but the shape of the style changes throughout the years. Right now, an oversized button-up denim shirt with matching jeans is the coolest combo.

STYLECASTER | How to Dress Up Jeans

Courtesy of NAKD.

Pocket Detailed Oversized Denim Shirt

I love the deep blue color of this oversized denim shirt.

STYLECASTER | How to Dress Up Jeans

Courtesy of NAKD.

Loose Cargo Denim

These cargo jeans are a perfect match to the pocket shirt—a key element of nailing a Canadian tuxedo.

 

STYLECASTER | How To Dress Up Jeans

iMaxTree.

With a Trench Coat.

If Karlie Kloss is wearing it, you know it’s a good outfit combo. A long black trench coat is a wardrobe essential and will give your jeans a high-fashion edge.

STYLECASTER | How to Dress Up Jeans

Courtesy of Ena Pelly.

Beckett Contrast Trench Coat

The large belt on this trench coat and leather detailing will elevate any look.

f

STYLECASTER | How to Dress Up Jeans

Courtesy of Levi’s.

80’s Mom Jean

Take notes from Karlie Kloss and opt for distressed jeans to give the trench coat a relaxed look.

 

STYLECASTER | How To Dress Up Jeans

iMaxTree.

With a Biker Jacket.

Biker jackets are one of the “it” jacket trends of 2023—your Instagram explore page is probably filled with them and even Kendall Jenner has jumped in on the trend.

STYLECASTER | How to Dress Up Jeans

Courtesy of Harley Davidson.

Fennimore Riding Jacket

This Harley Davidson racing jacket is the real deal.

STYLECASTER | How to Dress Up Jeans

Courtesy of Everlane.

The Original Cheeky Jean

If you’re looking for a classic go-to pair of straight-leg jeans, Everlane makes some of the best.

 

STYLECASTER | How To Dress Up Jeans

iMaxTree.

With a Faux-Fur Coat.

My absolute favorite thing to pair with jeans right now is a faux-fur coat. It adds a little drama to a cold winter day and I’m here for it.

STYLECASTER | How to Dress Up Jeans

Courtesy of Pretty Little Thing.

Plus Cream Soft Touch Shaggy Faux-Fur Coat

This shaggy faux-fur coat is just the one you need to wear with a pair of light-wash jeans. It’ll also look great with a slip dress for a night out. It’s available in sizes L-5X.

STYLECASTER | How to Dress Up Jeans

Courtesy of Good American.

Good Boy Jeans

The split hem on this pair of light-wash jeans will give them a subtle flair shape. This pair is available in sizes 00-24.

 

STYLECASTER | How To Dress Up Jeans

iMaxTree.

With a White Button-Down.

For a timeless look, a white button-down is always chic—but don’t be afraid to modernize it with cropped or cut-out options.

STYLECASTER | How to Dress Up Jeans

Courtesy of L’Academie.

Norman Built in Bra Shirt

STYLECASTER | How to Dress Up Jeans

Courtesy of Donni x Madewell.

Low-Rise Loose Jeans

Give your look a little Y2K love with this pair of (slightly) low-rise jeans. They sit lower on the hip without being uncomfortably low-rise.
STYLECASTER | How To Dress Up Jeans

iMaxTree.

With a Dramatic Blouse.

A puff sleeve, a big bow, eyelet lace and bright florals are all game-changers when it comes to a blouse. A good blouse will take your jeans from the office to happy hour to a weekend shopping date—and you can bet you’ll get a lot of compliments.

STYLECASTER | How to Dress Up Jeans

Courtesy of Farm Rio.

Sweet Floral Blouse

Farm Rio makes the happiest blouses in all sorts of colors and patterns. This one reminds me of spring.
STYLECASTER | How to Dress Up Jeans

Courtesy of Rollas.

Rolla’s East Coast Flare Jeans

A flared sailor-style jean always compliments are feminine blouse—these would look great with pointed toe boots.

StyleCaster Banner Newsletter


Share This Article