Spring Outfit with Boyfriend Jeans

Boyfriend jeans aren’t my normal silhouette of choice, but they’re trending right now so I thought we could talk about how to wear boyfriend jeans and who should wear them.

3 tips for how to wear boyfriend jeans

Boyfriend jeans have been around for a while, and the latest iteration of this trend is the “girlfriend” jean or the “slim boyfriend.” Basically all that means is they’re not quite as baggy as the boyfriend jeans of 2014, but they still have a loose, slouchy fit, and they’re usually a little bit destroyed. I found these slim boyfriend jeans at J.Crew, and they were 30% off last weekend. Woot!

As far as who can wear boyfriend jeans, I think they’re easier to wear if you’re taller and/or short-waisted, but there are ways to get around that (i.e. high heels, shorter top, etc.) Personally, I don’t love the look of boyfriend jeans because I prefer my jeans to be more figure-hugging, but they’re fun for a change.

3 tips for how to wear boyfriend jeans

Because they’re baggy, boyfriend jeans can look sloppy, so here are a few tips to pulling off the look with panache.

How to Wear Boyfriend Jeans

  1. Keep it structured on top. Whether it’s with a tight t-shirt or a fitted blazer or a moto jacket, you want to offset the baggy bottoms with something more form-fitting on top.
  2. Wear a delicate shoe. Pointy-toe pumps, high-heeled sandals, or strappy flat sandals all work well with boyfriend jeans. You can wear fashion sneakers, but I think that’s a harder look to pull of. I’ve also seen ballet flats work. Again, the idea here is to off-set the baggy pants with something more delicate and slimming on your feet.
  3. Add a feminine accessory. Since the boyfriend jeans are a little bit edgy, carry a leopard clutch, wear a lace top, throw on a statement necklace, or break out your favorite stilettos. Even if you’re going for the casual weekend look with Converse and a cropped sweatshirt, add diamond earrings or a colorful bag for a feminine flair.

Here’s my take on the look. These are the slim boyfriend jeans from J.Crew, and this is a similar pair for less at their Factory store. Here is a non-distressed version, if you prefer.

3 tips for how to wear boyfriend jeans

I kept it simple with a white v-neck tee that is fairly form-fitting. This is the Perfect White Tee from ThirtySomethingTees, and you can save 10% with code Jolynne10. For size reference, I’m wearing a medium.

3 tips for how to wear boyfriend jeans

These thong sandals have a casual vibe while the shiny gold coordinates with the necklace and keeps the look feminine.

3 tips for how to wear boyfriend jeans

3 tips for how to wear boyfriend jeans

A white t-shirt and blue jeans is pretty basic, and my shoes are a neutral, so I wanted an accessory to liven up the outfit. This leather lariat layering necklace from Stella & Dot is trendy and fun, and it draws attention up and away from the baggy jeans. It can be worn 4 different ways by removing various strands, but for this outfit, I kept it all together.

3 tips for how to wear boyfriend jeans

Finally, I added a red crossbody bag for a fun pop of color. A leopard clutch would be cute too — or leopard pumps, for that matter!

3 tips for how to wear boyfriend jeans

While I think this outfit works fine with the flat sandals, I also wanted to show you the look with heels. Generally, I think boyfriend jeans look better with heels, although I am more comfortable wearing them with flats.

I see a lot of pointy toe pumps with boyfriend jeans on Pinterest, an I admit I love the look, but that whole look feels a little “out there” to me, considering my casual lifestyle here in the ‘burbs. These neutral wedge sandals are a great way to elevate the look (bwahaha! I’m punny, aren’t I?) without getting all fancy with stilettos. They’re a little more practical than pumps while still giving the look a more uptown style than the flat sandals.

I’d love to hear your thoughts!

3 tips for how to wear boyfriend jeans


J.Crew slim boyfriend jeans (similar for less) // perfect white tee (similar for less) // Stella & Dot layering necklace // assorted Alex and Ani bangles // Déjà Vu Stone Studs (worn backwards) // Sam Edelman gold thong sandals // similar wedge platform sandals // red crossbody

Tune in tomorrow for the last outfit in my 27 Days of Spring Fashion style series, and be sure to visit Cyndi and see the spring outfit she’s styling today!

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41 Responses

  1. I can totally get behind this look. It is very hard for me, normally, to see myself wearing these. But I think you nailed this, and I may even pick some of these up now!

  2. Thanks for the great tips on how to make this look work.. I like the comfort of boyfriend jeans but I hate looking sloppy. This advice will be very helpful.
    You look Fab, BTW

  3. I agree that I struggle with this look. I like it when I see others, but feel so sloppy when I try it. I may have to try the new slimmer versions. It looks good on you with both pair of shoes. I wouldn’t have thought to pair them with heels.

    I am interested to hear about your trip to Savannah. We are spending a day there this summer when in Hilton Head and I’ve never been to the Carolina’s. What would be your suggestion for a family if you were only there for a day? Any ideas? My girls are 9 & 13..

    Have fun!

  4. I think they look great on you! I personally think for women who are bigger in the hip area boyfriend jeans might be a little kinder to their body shape. But also at the same time if you have thicker calves this style works well for you too. I am learning about jeans and it seems I have been buying more boyfriend jeans because they feel better wearing them but might not necessarily look better on me. But I will say a pair of white boyfriend jeans are more forgiving on my body shape than a pair of white skinny jeans. I wish I could post a picture of myself in the outfit I wore to a birthday dinner last night for you to tell me if it worked or not. I had an off the shoulder top on with a pair of white destroyed boyfriend jeans and wedges. It’s hard to know if it worked for me or not!

  5. I’m not one for boyfriend jeans either. I tried them on once; the way I looked in them made Larry and me laugh. I like your feminine flats and the higher sandals.

  6. I don’t like the boyfriend jeans either. You styled them well though. The last 2 looks on you were great and really wearable. The camo from yesterday and the black and white outfit from the day before was my favorite. Enjoy Savannah!

  7. I like boyfriend jeans mainly because of comfort. Thanks for showing the concepts behind styling them. You look cute as always!! Julie L

  8. I love this look. I live in my slim boyfriend jeans! I even have them in white. I am tall, so maybe that’s why I Iike how I look in them. Great post!!

  9. Thanks for doing this! I have a pair and I love them for the comfort but they aren’t the most flattering on me. Still, they have their place for bombing around town or even just when I’m home.

  10. Not a fan but anything looks good on you. I prefer fitted also. But great for some people.So glad you styled. Enjoy Savannah.

  11. I haven’t liked the boyfriend jeans because they are too sloppy looking but I LOVE the girlfriend jeans because I don’t really care for the skinny jeans. I just like mine plain and straight and the girlfriend jeans give me the option of something different without being too baggy.

    I have to say I just can’t get my head around wearing pumps with these kind of jeans. I mean – to me – the reason for the more casual jean is to be comfortable not tromping around in heels. LOL. But I have to admit when I see them on someone else with high heels they do look cute. It’s just not for me. Give me sandals or sneakers! 😉

    I think these look really cute on you.

    I hope you have a FANTASTIC time in Savannah!

  12. I love this outfit with the gold flats, but not with the wedges. I know you think you look better in skinny jeans, but I think you look 10 lbs thinner in these!

  13. You definitely pull them off beautifully, but I agree, they’re not for everyone (myself included). You have your height and longer legs working for you with these for sure. I’ve tried the baggier and slimmer kinds, and they just don’t do me any favors at all. I think in my case, it’s rolling the wider leg cut on my shorter legs. Although, I do have some girlfriend chinos from last year that I still love, oddly. They’re not the most flattering for me, but I love them anyway! 😉

  14. I do have a pair of boyfriend jeans that are the most comfortable jeans ever. However, I sized down 2 sizes. They really probably fit more like the girlfriend jeans. They aren’t very baggy, just a little loose.
    They feel like a pair I have had forever & are so soft. Nice job styling!

  15. I love the boyfriend jeans! My hips are curvy so the boyfriend look isn’t slouchy on me. I love to wear a black fitting tee and neutral wedges. I think this look is great and you are rocking it!

  16. As a total pear shape (big hips/butt – 🙂 ) I LOVE boyfriend jeans. I have been looking to test out the girlfriend jeans this year. I think this style is really dependant on body type, as I find it really hard to find a pair of “skinny” jeans that look good on me, and the relaxed fit of the boyfriend is a little more forgiving for my figure. Thanks for the tips on wearing them – I have the tops nailed, but need to work on the shoes. Thanks for stepping out of your usual zone to show a different style. 🙂

  17. I think you pull off this look perfectly!! I like both the gold sandals and wedge too!! I need to get some wedges and now, boy/girlfriend jeans too!!

  18. I think you look fab in them!!!! Love them with the wedges. To me it adds height to the boxy jeans. I have a pair and i love them!!!! Im tall and log waisted, so i usually wear them with a lace asymmetrical top or some sort of interesting hem line. I can’t do the tucked in fitted shirt because im apple shaped and a little boxy myself!! LOL . I think you rock this look!!!!

  19. I love a good boyfriend jean. The key is finding a great fit. I have tried the J. Crew boyfriend & liked them. My favorite is Talbots boyfriend jean, and I have tried on a lot of boyfriend jeans. They are a bit slimmer, regular & petite sizes, come in colors, and distressed or not. No not an employee. I am 5’3″ and wear the petite size. I have styled them with tee & cardi (fitted or long), a sleeveless blouse with fitted cardi or just a sweatshirt. You are absolutely right that delicate shoe is a must — however, if you wear a sneaker a slim sneaker looks best. Thanks for all your great tips. Enjoy Savannah.

  20. You definitely look good in them and the key is proportion and not too loose. I have a pair that I love that took me forever to find since many I tried hit my leg in an area that made me look short and stumpy. I too love the pinterest look with pointy pumps but that look doesn’t fit in with my casual Hawaii lifestyle. Thanks for sharing looks that are out of your comfort zone.

  21. I like this look on you. I also have a few pairs of boyfriend:girlfriend jeans and I almost always wear them with heels. The flat sandal is cute, but wearing flats makes me feel frumpy, and I am 5’8″!

  22. You look great in these jeans…I prefer the flat sandals…actually they would also look great with the lace up flats you wore in the previous post as well!

  23. I think the boy friend jeans looks really good on you. I don’t like the high wedge with them. I think the flats are best. I have never tried these jeans on before, as I’m 55 yrs. old and don’t like to wear the distressed look. I have 2 grown girls and just feel funny if I dress in distress when its more for their age. Just my thinking. 🙂 I have jeans still in my closet that are straight leg, light wash, that I love rolled and worn with slip on sneakers and a t-shirt and/or sweatshirt. They give more of a casual look from the skinny, but not quite as baggy. I’m 5’3″ so not sure how the boy friend/girl friend would look on me. Maybe I should try them. 🙂 Enjoy your trip…I bet you are so excited. I’m so ready for a vacation and warmer, sunnier weather.

  24. Great advice Jo-Lynne! Boyfriend jeans aren’t my favorite either, but they do look much better with fitted tops and feminine accessories. Love those gold flats!

  25. Love the flat gold sandals with this look! Now I’m going to have to try this look! I typically only do skinny jeans. I feel sloppy in boyfriend jeans but seeing you rock them gives me confidence!!

  26. I LOVE boyfriend jeans and I think this is a great look for you (just different)!! I usually just go casual with a t shirt and flats, but I love your idea to add a more feminine top and shoes. I’m definitely going to start mixing mine up a little! Thanks for the inspiration!

  27. These look great on you! I love boyfriend/girlfriend jeans because I am pear shaped with thick calves. The looser fit in the legs is much more proportional for me.
    I would love to see you style these with a dressier top too.
    P.S. Has ANYONE except a fashion blogger in a photo ever actually worn these jeans with heels? I’ve never seen it!

  28. Hi Jo-Lynne,
    These look great on you. Really young and fresh and relaxed. I like them best with the wedge sandals.
    I don’t own a pair of boyfriend jeans, although on a warm day, it would be so much more comfy than skinnies. I’ve always assumed they’d look too sloppy, but the way you styled them, with the feminine touches, really works. I’m off shopping! Lol

  29. I think you look great in the boyfriend jeans and flat shoes. Not a fan of wearing them with heels. At all…just saying lol. Thanks for post.

  30. Luv the boyfriend jeans and I keep it simple on top.
    Wear a great pair of heels and rock it with great jewellery. I wear scrubs all day, so it is fun experiment. The jeans look great on you!

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