How to Style: Pants & Skirts

19 Cool Boyfriend Jeans Outfits You’ll Wear on Repeat

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You know those days when you just want to throw on something easy and comfortable but still look cute? For me, that’s when I always grab my boyfriend jeans.

They have this effortlessly cool vibe that I just can’t get enough of. To show you what I mean, I’ve pulled together 19 looks that are perfect for everything on your calendar.

1. The Cozy Cool

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You can stay warm and still look totally cool in a light-colored hoodie paired with some light-wash boyfriend jeans that have a little distressing. A long wool coat thrown over the top just completes the whole vibe.

Finish it off with sneakers and a beanie. This outfit formula is one I’d reach for on a chilly day or for a super casual weekend.

2. The Summer Stunner

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I love putting together a perfect summer-ready look. Start with a camisole top and some distressed boyfriend jeans with raw hems. Then add a straw handbag and some white platform sandals.

A little bit of gold jewelry adds a touch of glam. Honestly, this look is just what I’d wear for a beach day or a cute summer picnic.

3. The Pretty in Pink

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If you want to make a bold statement, this is it. Grab a bright pink long-sleeve top with a mock turtleneck and pair it with light-wash high-waisted boyfriend jeans.

A pair of bright pink pointed-toe heels really elevates the whole thing. This is such a fun outfit for a girls’ night out or a date night.

4. The Athleisure Queen

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I’m obsessed with this combination. A tight-fitting black long-sleeved crop top with high-waisted light blue boyfriend jeans and some platform sneakers is such a vibe.

For an edgy touch, just add a thick choker necklace. This is the ideal outfit for running errands or just a casual hangout with friends.

5. The Candy Crush

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This is such a sweet statement look that lets you tap into your fun side. A bright pink sweatshirt looks so good with light-wash baggy jeans and some beige chunky sneakers.

I’d wear this for a casual day of errands or for a movie night with friends.

6. The Edgy Rocker

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Okay, this look gives off major 2002 pop-punk princess energy and I am so here for it. You just need a black leather motorcycle jacket with a plain white T-shirt and some light-wash boyfriend jeans.

To finish the look, some black combat boots give it that edgy vibe. This is the perfect outfit for a concert or a night out.

7. The Cozy Chic

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When it gets chilly, I love layering. A dark oversized leather trench coat over a hoodie is such a cool combo, especially with light blue loose-fitting boyfriend jeans.

Just add some chunky sneakers and tinted sunglasses for a vibe that’s totally street style meets ultimate comfort. This one’s a go-to for a cold day or any casual weekend plan.

8. The Classic Casual

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For a timeless look that’s super casual, you can’t go wrong with distressed light-wash boyfriend jeans and a gray long-sleeve top with gray sneakers.

A burgundy shoulder bag adds the perfect little pop of color. I love this for running errands or a laid-back weekend brunch with friends.

9. The Boss Babe

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You can totally dress up your boyfriend jeans. Just try a cropped fitted blazer with a cropped black top.

Then, add some black rectangular sunglasses, a black handbag, and sneakers. The result is a look that’s so chic and still so comfortable.

10. The Boho Babe

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For a boho aesthetic that makes me dream of music festivals, try a patterned crop top with light wash high-waisted boyfriend jeans.

Finish it with statement sunglasses and some simple black slide sandals. This one is such a good choice for a festival or just a casual summer get-together.

11. The Preppy Perfection

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This preppy look has such a classic, collegiate feel. Just pair an oversized black cardigan sweater with a plain white T-shirt and light-wash high-waisted boyfriend jeans.

Some black leather loafers give it a polished finish. I think this outfit is a great option for a casual office day or a weekend brunch.

12. The Bold and Beautiful

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You can make a statement with a bold striped long-sleeve top and high-waisted boyfriend jeans.

Just add some sleek black sunglasses and black strappy sandals for a chic finish. I would totally wear this for a casual dinner or a weekend trip.

13. The Utility Chic

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I love leaning into the utility trend. Combine an army green cropped jacket with a beige top and light-wash high-waisted distressed boyfriend jeans.

For a little bit of sophistication, finish the look with snakeskin print pointed-toe flats. This outfit is ideal for a day of shopping or just exploring a new city.

14. The Boho Beauty

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You can really embrace a boho vibe with a light blue ruffled top and light-wash boyfriend jeans. Add some white sunglasses and gold jewelry to complete the look.

A brown belt and sandals create a style that feels laid-back but still so stylish. It would be so good for a summer festival or a casual day with friends.

15. The Sleek and Chic

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For a sleek and chic look that gives off total confidence, I love a black sleeveless crop top with light-wash high-waisted wide-leg jeans and black pointed-toe heels.

This is a perfect outfit for a semi-formal event or a really nice dinner date.

16. The Minimalist Maven

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Let’s be real, sometimes simple is the chicest way to go. You can keep it simple and so stylish with a one-shoulder top, high-waisted light blue boyfriend jeans, and platform sandals.

This is just what I’d pick for a casual dinner or a day of shopping.

17. The Relaxed and Refined

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For a look that’s relaxed but still so refined, like you just woke up looking this good, grab a loose-fitting white button-down shirt with the sleeves rolled up. Pair it with light wash boyfriend jeans.

Some simple slide sandals and oversized sunglasses add a chic touch. This is a great outfit for a casual office day or a weekend brunch.

18. The Pattern Play

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Mixing patterns is so fun. You can totally do it by pairing a houndstooth patterned jacket with a black top and light blue jeans, then adding some leopard print heels.

A brown belt and a black handbag give it a polished finish. I think this outfit works so well for a casual day at the office or a lunch date with friends.

19. The Off-Duty Diva

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I love a white off-the-shoulder crop top with full sleeves and light wash distressed high-waisted boyfriend jeans. The combination creates a look that’s just so effortlessly chic.

It’s the perfect cool mom vibe for a casual day out or a lunch date.

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