30 Best Shoes to Wear With Boyfriend Jeans For a Chic Look

• The most common way to wear your boyfriend jeans is to roll them at the cuffs. This adds a little structure to the looser fit of the leg and looks super cute with a variety of shoes.
• Look for boyfriend jeans that fit mostly snug around the hips, are slightly looser around the thighs, and are medium baggy around the calves.
• Distressed denim is a popular choice for boyfriend jeans and gives them that slightly edgy factor that makes them so fun to wear.
• Boyfriend jeans are quintessentially casual, but by pairing them with specific pieces as well as shoes, you can make them even appropriate for work! (Depending on your job, that is. They would not be acceptable for office jobs, let’s put it that way!)
• Because boyfriend jeans typically hit right at the ankle or above it, adding some height and elongation through heels is a great way to visually lengthen the body.

Now let’s look at some examples!

↓ 30. Block Heel Sandals

Most of the time, boyfriend jeans are worn rolled at the cuffs. This provides the perfect opportunity to show off some glam jeels. With this look, opt for some dazzling rhinestone block heels and pair them up with some distressed high waist boyfriend jeans. A cute tee and some fun accessories add the finishing touches to the look.

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↓ 29. Platform Sneaker

Low top sneakers give this look a more feminine and shapely finish by showing off a little ankle. Dark or bright colored low tops are acceptable and are the perfect footwear during the summertime.

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↓ 28. Booties

To bring some chic vibes to your boyfriend jeans, pair them up with some snakeskin stiletto booties. This is a gorgeous semi-casual outfit you can rock for just about any occasion. Whether you are running errands, grabbing coffee with friends, or even heading to a concert, this look does it all. If you like wearing booties, don’t miss out our recent post on the best ways to wear Booties with Jeans.

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↓ 27. Pointy Pumps

For a chic yet casual work outfit look, check out this ensemble. Whether you have lunch with clients, a date with your guy, or are just looking to break out of a boring work attire routine, this stylish combo of a wrap top and boyfriend jeans paired with nude pumps will do the job nicely. (Or at least help you do yours!) This is a great way to rock boyfriend jeans if you are petite. Nude heels also help elongate the leg.

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↓ 26. Flat Sandals

Flat sandals are the typical summer beach style shoe and come in such a vast amount of styles that finding your ideal pair is easy-peasy. Here is a super casual outfit option you can try asap. Pair a simple and cute graphic tee with your favorite pair of boyfriend jeans and add some slip-on sandals. To make this look a little more put-together, make sure to style your hair and add a belt for good measure.

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↓ 25. Trainers

We love this ultra-chic look incorporating a metallic blue shirt, pale blue jeans, and white trainers. If you love an outfit that you will feel uber comfortable in while also looking super stylish, this is the one for you.

While this ensemble works great for a variety of occasions, this would make a great party look if you are trying to keep things lowkey while also being chic. Go for a slightly more fitted version of boyfriend jeans with minimal rips and pair with a smoky eye makeup look to keep the look from getting too casual.

↓ 24. Knee-High Boots

Now, here is a winter look we love. Keep those ankles warm by wearing your favorite boyfriend jeans with a pair of slouchy knee-high boots. Not only is this outfit a great example of how to make a super casual look seem chicer and even semi-professional, but you can tweak it for almost any type of occasion.

We love the juxtaposition of a blazer with slightly baggy boyfriend jeans. Pair it with a simple black top and a deep red scarf for a pop of color. Also, check out what outfits to wear with knee-high boots if you are looking for ways to style a chic outfit!

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↓ 23. T-Bar Heels

Want to make your boyfriend jeans party-ready? Pair them up with some gold t-bar heels for a splash of flair you’ll love dancing the night away in.

↓ 22. Platform Slip-On Sneakers

Nothing says casual and stylish like a pair of boyfriend jeans and platform slip-on sneakers. This is a great look for running errands or just chilling on the weekend. You’ll feel put-together without having to overthink it. Win-win, we say.

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↓ 21. Chunky Chelsea Boots

If you love pushing the envelope a bit with your everyday fashion, you might want to check out this look right here. By pairing a patterned top with a short kimono, baggy boyfriend jeans, and some chunky Chelsea boots, you are sending a bold and powerful message to the world: Look Out, Because Here I Come.

↓ 20. Diamante Sandals

Pop on some diamante or rhinestone-studded flats for a go-to pairing your boyfriend jeans will look great with.

↓ 19. Timberlands

A great fall look is this one right here, combining baggy, distressed boyfriend jeans with a deep green sweater and Timberland boots. We love it!

Also, check out what outfits to wear with Timberlands for more inspiring looks!

↓ 18. Slip-Ons

As aforementioned, there IS a way to rock your boyfriend jeans at works, especially if you work in fashion. Check out this look which combines some minimally distressed boyfriend jeans with a black silk top, a blazer rolled to the elbows and a chic designer bag. Accessorize with sunglasses.

↓ 17. Jordan Sneakers

How about a leather version of the boyfriend jean?! Super edgy and the perfect ensemble for a concert. Pair them up with some Jordans, a white tee, and a leather jacket.

Need more ideas for what outfits to wear with Jordans? Check out the link for our article on it!

↓ 16. Birkenstocks

There is so much to love about this classic pairing of Birkenstocks and boyfriend jeans. Here is one of the rare examples you’ll see of boyfriend jeans sans distressed denim or even a roll at the cuff. Pair with a white top for a look you can rock any day of the week with confidence.

↓ 15. Gladiator Heels

Believe it or not, the denim on denim is not the most interesting factor in this look! Nope. We will have to give that award to these killer gladiator heels which are so awesome, we think every girl should probably own a pair.

↓ 14. Bright-Colored Vans

Need a go-to vacation look? Pair up your slim-fitting boyfriend jeans with some pop-of-color Vans to keep things interesting!

↓ 13. Wedge Heels

For a youthful look, pair white slim-fit boyfriend jeans (no roll at the cuff) with some t-bar wedge heels. Add a bright yellow tank and a funky necklace to complete the outfit.

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↓ 12. Studded Mules

For a classy take on your average weekend attire, check out this look. Pair some slim-fit boyfriend jeans with a slightly loose sweater with soft, muted colors. Lastly, slip on some studded mules. Not only are mules super convenient when you are on the go but they are innately stylish as well. A tote bag and some simple jewelry are all the accessories you need!

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↓ 11. Combat Boots

For cozy fall and winter wear, try pairing your slim-fit boyfriend jeans with a pair of black studded combat boots. Top it off with a cute knit turtleneck sweater and a designer bag.

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↓ 10. Converse

Need a cute back-to-school outfit? Here it is! Pair some boyfriend jeans with your favorite pair of Converse, along with a striped top and cute plaid vest.

Also, be sure to check out what outfits to wear with converse for a chic look!

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↓ 9. Biker Boots

Here is a casual street-wear look that is giving us serious style envy. A loose white tee tucked slightly into a pair of boyfriend jeans with some biker boots is a great weekend look you’ll feel comfortable and cute wearing.

↓ 8. Cap Toe Pumps

These cap-toe pumps are so great for bringing a bit of a vintage, old-school vibe to your outfit. Pair them up with distressed denim boyfriend jeans, a pale brown camel coat, and a red handbag.

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↓ 7. Peep-Toe Wedge Boots

If you are running errands this week and want to look chic and fly while doing it, give this outfit a whirl. A sheer black top work over boyfriend jeans and peep-toe wedge boots is a fantastic option that can be dressed up or down according to the day’s events.

↓ 6. Loafers

The fun doesn’t stop! We can’t get enough of these casual styles that incorporate boyfriend jeans so well. For a ridiculously simple look, try pairing a white tee (or bodysuit, to eliminate having to adjust how tucked in your shirt is all day) with some slim-fit boyfriend jeans and a pair of brown loafers. (Pro tip: whenever you want to feel like you have your life together, simply pop on a pair of loafers. They make you look and feel like a put-together, successful woman almost instantly.)

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↓ 5. High-Top Converse

For casual-chic, you can’t get better than this. Pair a white top with a light-wash pair of boyfriend jeans, a slightly oversized taupe blazer, and a pair of high-top Converse. A small over-the-shoulder purse and slicked back chignon provide the finishing touches to this alluring ensemble.

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↓ 4. Greece Slides

Stay chic this summer with a cute sleeveless top and Greek-style slides. Perfect for staying cool while also showing off your love for fashion. Accessorize with a cute pendant necklace and some bracelets.

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↓ 3. Snakeskin Sneakers

Need a go-to weekend look? Pop on some snakeskin sneaks, your favorite pair of boyfriend jeans, and a graphic tee. It’s all about the little touches with this look so try knotting your tee at the waist, rolling the cuffs of your jeans, and opting for distressed denim.

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↓ 2. Ankle Strap Heels

Dress up your boyfriend jeans a bit to make them party-ready by pairing them with some ankle strap heels, a black camisole top, and a long cardigan. Add an animal-print belt to tie the look together.

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↓ 1. Two-Strap Sandals

For our final suggestion on stylish shoes, give these two-strap sandals a try! They are effortlessly stylish and pair really well with boyfriend jeans, especially distressed, medium wash boyfriend jeans. Pair with a white tee and an olive green safari-style jacket. Accessorize with some bracelets and a clavicle necklace. And voila!

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