The 10 Best Shoes to Wear With Your Boyfriend Jeans

From heels to loafers.

boyfriend jeans


Boyfriend jeans, though a heteronormative term for a popular denim style made for anyone who feels like wearing them, are the kind of staple that likely won’t ever go out of style. Their concept is simple yet effective: jeans that feel relaxed and slightly subversive. Many attribute the origins of boyfriend jeans to Marilyn Monroe circa 1960s on the set of Misfits. But their prominence has only gained momentum over the last several years, particularly for those who aren’t fans of the denim trend on the opposite side of the spectrum: skinnies. 

Wherever your allegiance falls, a pair of boyfriend jeans is worth adding to any wardrobe. However, because of their looser proportions, they can be more difficult to pair with shoes. Ahead, 10 footwear styles that work well with your favorite boyfriend jeans (and where to shop them).

01 of 10


Styling a relaxed pair of denim with sneakers is leaning into the androgynous aesthetic of boyfriend jeans. Consider doing an 'undone cuff' on your denim to let your ankles show a bit.

Tournament Sneaker
Jack Erwin Tournament Sneaker $165.00
Made US 990v5 Sneakers
New Balance Made US 990v5 Sneakers $175.00
02 of 10

Strappy Sandals

A pair of sleek strappy sandals contrast the laid-back vibe of boyfriend jeans, equating to a *chefs kiss* combination you can wear from date night to a weekend dinner with friends.

Ellie Caramel Patent Sandals
Miista Ellie Caramel Patent Sandals $350.00
Tobias Sandals
Emme Parsons Tobias Sandals $455.00
03 of 10


Give your boyfriend jeans the '90s treatment by styling them with a pair of mules. Extra points if they’ve got a splashy color, texture, or print.

Dylan Sebrina
SheKudo Dylan Sebrina $229.00
Woven Square Heels
Reike Nen Woven Square Heels $360.00
04 of 10

Cowboy Boots

Hear us out—western boots may seem like an adventurous pick, but they look insanely cute with a pair of slouchy jeans tucked into them. Finish the look with an oversized tee or button-down shirt.

Mermaid Doodle Boots
Brother Vellies Mermaid Doodle Boots $1,150.00
Round Up Wide Square Toe Western Boot
Ariat Round Up Wide Square Toe Western Boot $150.00
05 of 10

Block-Heel Pumps

If a stiletto with baggy jeans feels like too stark a contrast for your personal style, consider a block-heel pump instead. The proportions play out nicely.

Villa Flats
LoQ Villa $325.00
Mari Giudicelli Flats
Mari Giudicelli Loren Ballerina $325.00
06 of 10


A flatform sandal and boyfriend jeans feel exceptionally effortless and cool for spring and summer. Wear with your favorite tee and anklet to pull the look together.

Heather Sandals
Flattered Heather Sandals $179.00
Nicky Sandals
Staud Nicky Sandals $395.00
07 of 10

Classic Pump

If you run a Google search on boyfriend jeans, many of the celebrity images you’ll see show ladies like Rihanna and Sarah Jessica Parker wearing this denim style with classic pumps. It’s a tried-and-true combination that works for everyone.

Kuma Pumps
Neous Kuma Pumps $597.00
Danna Pointed Toe Stiletto
Sam Edelman Danna Pointed Toe Stiletto $84.00
08 of 10

Slingback Heels

There's something distinctively Carrie Bradshaw-esque about a pair of slingback heels. So, it's only fitting we’d suggest wearing them with a pair of cute boyfriend jeans.

Stacey Heels
Ma’am Stacey Heels $310.00
Soray Slingback
Cult Gaia Soray Slingback $428.00
09 of 10

Flat Sandals

Go for a pared-down, minimalist aesthetic with slouchy jeans (not cuffed) and flat sandals. An oversized poplin button-down shirt would pair perfectly.

Atelier Alessano Sandals
ATP Atelier Alessano Sandals $250.00
Style 10
Amanu Style 10 $250.00
10 of 10

Heeled Loafers

While flat loafers may not feel quite right with boyfriend jeans, a pair with a slight heel does the trick. Wear the two with a cute cardigan or camisole if it’s hot outside.

Nono Loafers
Nomasei Nono $365.00
Kitty Loafer
Labucq Kitty Loafer $420.00

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