9 Date Night Outfits With Boyfriend Jeans

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Boyfriend Jeans Outfits You Can Wear On a Date

Street Style
Christian Vierig / Getty Images

You may have heard that skinny jeans aren't the only go-to denim for date night denim anymore. Boyfriend jeans — once just the jeans you borrowed from your guy's closet — have evolved into a slimmer, more stylish pant that can flatter any shape. When you learn a few key styling tips, you'll be surprised at how you can create pretty date night outfits with these comfortable jeans to wear to the movies, dinner and beyond.

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Boyfriend Jeans and Sleeveless Top

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This date night outfit is as cute as it is easy. Calvin Rucker

You're probably used to reaching for jeans and a cute top as an easy outfit you can pull together at the last-minute to wear on dates. We think the most current way to wear jeans and a sleeveless top for date night is to choose distressed boyfriend denim. Ripped, patched denim, finished with a casually rolled cuff, plays against your fanciest silky top in a way that says you dressed up for the date, without trying too hard.

Style Tip: Don't get sloppy with your shoes in this outfit. A great pair of black heels or ankle boots keeps you looking stylish.

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Slim Ripped Boyfriend Jeans and Leather Shirt

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Leather adds edge to a boyfriend jeans look for date night. BLKDNM

Leather is a key trend for the colder months. Here's how to wear it on a date with boyfriend jeans, to create a look that's trendy but still approachable, for drinks or dinners out. Pair slim boyfriend jeans with a well-fitting leather (or leather-look) shirt. Distressed boyfriend jeans that just skim your curves are more forgiving than skinny jeans, while still highlighting your figure. Finish the outfit with high-heeled shoes, to extend your leg line for a slenderizing effect.

Style Tip: When considering how (or whether) to cuff your boyfriend jeans, focus on length. Jeans that hit just above the tops of ankles highlight your legs at their slimmest point — and show off great shoes.

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Boyfriend Jeans and Trench Coat

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A short trench makes a sexy topper for boyfriend jeans. Citizens of Humanity

Pull a classic short trench coat over a basic tee-shirt and boyfriend jeans, for an instantly date-ready outfit. What makes this look sexy and un-boring is the choice of a colored trench — instead of the expected beige version — and pointy high-heel shoes. This is a great outfit to wear on a date to the movies or for long walks outdoors.

Style Tip: Dress up this easy date outfit with a notice-me pendant, or multiple chain necklaces.

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Menswear-Inspired Boyfriend Jeans Outfit

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This date night look is a cheeky mix of the masculine and feminine. Lucky Denim

Here's a look that's a favorite of celebrities for its cute, androgynous appeal. Boyfriend jeans are a fresh choice for date-night dressing, especially when styled with separates and accessories inspired by a guy's closet. Create a coquettish look you can wear on dates by pairing slim-fitting boyfriend jeans with a textured blazer, man-style hat and trendy wedge-style ankle boots. Roll jeans so they just cover the tops of boots, for a long leg line.

Style Tip: To look cheeky and feminine in this guy-inspired ensemble, keep the layers fitted, not baggy. Add a statement necklace or a chunky scarf to finish your outfit.

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Boyfriend Jeans and Feminine Top

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A pretty top adds feminine charm to boyish jeans. Madewell

You've probably heard the fashion maxim that you can create a fresh effect in your outfits, by mixing masculine and feminine elements. We love the look of relaxed boyfriend jeans worn with an ultra-feminine top, as in this outfit by Madewell, for a date night look you could wear to concerts, parties and get-togethers with your friends.

Style Tip: For concerts or outdoor events, have fun with the 90s grunge fashion trend — and keep an extra layer on hand in case the weather cools — by wrapping a plaid shirt around your waist.

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Ripped Boyfriend Jeans and Fitted Cardigan

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Slim distressed boyfriends are date-ready with long and lean separates. American Eagle

Here's a no-brainer outfit you can wear on dates out to dinner, drinks, parties and beyond. Pair distressed, cuffed boyfriend jeans with a slouchy tee-shirt and a fitted cardigan sweater. Add a pair of high heels and a few pieces of jewelry to dress up your look — such as a pendant necklace and bangle bracelets — and you'll be ready for a night out in style.

Style Tip: When wearing trendy cuffed jeans that end above ankles, try pairing them with an ankle-strap shoe. This defines your leg at the slimmest point and helps make your legs look slimmer in boyfriends.

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Printed Boyfriend Jeans and Sheer Top

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A sexy sheer top is balanced by relaxed printed jeans. Marc by Marc Jacobs

We love how a patterned boyfriend style jean looks feminine, without being overly cutesy, because of the boyish fit. Paired with a sheer top that shows off strategic skin, you've got a guy-candy outfit that your date won't be able to stop looking at.

Style Tip: Swap the flat shoes pictured here for nude heels that closely match your skin tone, to create a longer leg line that visually slims you all over.

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Boyfriend Jeans and Shearling Jacket

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Shearling is trendy and warm on date night with boyfriend jeans. Polo Ralph Lauren

Shearling is a major style trend for fall and winter this year. You'll look current on your casual dates this season in an outfit of relaxed boyfriend jeans, a pretty sweater and waist-length shearling coat.

Style Tip: Belt looser jeans to define your waist and tuck the front of your sweater in so you don't look boxy.

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Boyfriend Jeans and Black Blazer

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A fitted black blazer creates shape over relaxed boyfriend jeans. Standards and Practices

Want to wear your ultra-distressed boyfriend jeans on a date to look stylish? Pair them with a tailored black blazer. A tuxedo-style jacket or fitted blazer adds structure to a relaxed jean style. Look for a jacket that fits perfectly at the shoulders and nips in at the waist, to highlight your woman's shape. For the sexiest effect, wear the highest heels you can stand with this outfit.

Style Tip: Jeans this creative call for unfussy hair. Leave your locks loose and let your natural texture show.