Boyfriend Shorts – How to Wear & Style

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Today let’s talk about one of my favorite read to ready pieces, boyfriend shorts.  When you go to the University of Florida for college, there are a ton of SEC rivals.  Each school has a way of playfully roasting/making fun of the other one.  For some reason, UF fans since Gainesville is in the middle of the state and not a metropolitan hotspot……the famous one liner is always “UF Fans love to wear jean shorts“.  Pretty much those horrible, ill fitting 1990’s jean shorts is the reference point.  We aren’t even going to discuss the mom jean shorts phenomenon that all the “youths” are wearing, with the cropped shirts and forehead hair bands.  There is no festival going on, just stop with the mom shorts.  They don’t look good on anyone.  Now enter in the boyfriend shorts.  They are an appropriate length, have a great structure to them and you can style them up or down.  This distressed boyfriend shorts pair HERE from Rag & Bone is my ultimate favorite.  They don’t bag out or grow with multiple wears.  The denim gets softer and softer which each wear.  They sit perfectly right at your hips and are an appropriate length.  You will find yourself reaching for them over and over due to have comfortable they are.  This is pretty much my Summer staple uniform.  I also linked under $25 options for every piece I listed because I’m an overachiever like that.

Boyfriend Shorts – How to Wear and Style

Rag & Bone Boyfriend ShortsBoyfriend Shorts, Rag & Bone Rag & Bone Boyfriend shortsMadewell bucket bagJoie Top, Rag & Bone ShortsClose up Boyfriend shorts

Boyfriend Shorts || Rag & Bone Shorts HERE SHOPBOP (I recommend sizing down one size).  Under $25 options here and here.

Grey Tee || c/o SHOBOP Joie find HERE. Under $25 options here and here.

Sandals || UGG find here.  Under $30 options here and here.

Bucket Bag || Madewell find here and SHOBOP Bucket Bag HERE.  Under $30 option here.

Sweater || Nordstrom find here.  Under $25 here.

Sunnies || SHOPBOP Karen Walker HERE.  Under $25 here.

Necklace || Baublebar find here.

Nail Polish || Essie Fiji here.

Bracelets || David Yurman here, here, and here.  Watch Cluse here.


What is your favorite staple Summer pieces?  Do you have a pair of boyfriend shorts?  How do you like styling them?  I hope everyone is having a great start to their week!  I was at the Pearl Jam concert late last night so hello massive cups of coffee today!

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43 responses to “Boyfriend Shorts – How to Wear & Style”

  1. Jesica says:

    I’ve never been a short-shorts girl so I loooove the boyfriend shorts! Plus distressed denim… always a win. You’ve styled them perfectly of course :)

  2. I love a good pair of boyfriend shorts. I just don’t get the tiny shorts, those jean underwear don’t look good on anyone, give me comfortable boyfriend shorts any day!

  3. Boyfriend shorts are so cute and I love that they’re comfy too! Love that necklace too! <3, Pamela Sequins & Sea Breezes

  4. I love the more relaxed look of shorts…especially the ones you have on!! You know what’s so funny…I’ve actually never owned a pair of jean shorts, not even during my time at UF haha! xo, Biana –BlovedBoston

  5. Jenn says:

    Really cute! I don’t have a cute pair of jean shorts anymore, but I think I need to find one!

  6. Rachel says:

    Love this look! Jean shorts that fit/look right can be so hard to find but of course you did it ;)

  7. Florida fans totally wear jeans shorts! But, you’re are super cute and I love your wedges. i always seem to get my shorts too big and the slouch after a while, not a good look. The R&B ones are seriously adorable!

    Go Dawgs!
    Whitney & Blaire
    Peaches In A Pod

  8. Nadine says:

    No no no my friend. Gator fans dont wear jean shorts they wear jorts! Hahahaha. But you are pulling this look off :)

  9. Lindsay says:

    I need a great pair of boyfriend asap! These look great on you and can we talk about your hair? Your highlights are perfection!

  10. Owen Davis says:

    Love this look! I hardly ever wear shorts because let’s be honest my ass is huge so the shorts always ride up and I’m constantly pulling them down!!! UGH!

  11. Caroline says:

    Love this whole outfit and I would definitely wear it!! :-) We have some Billabong shorts at work that are just like those too. Also KUT from the Kloth makes a boyfriend short. Just in case you’re interested in getting more haha. Since I work at a store that was created for moms, I am very anti-mom jeans. Like no no no. Haha. Thanks for sharing and have a great day!! :-)

  12. Lindsay says:

    Oh you little overachiever, you! Thanks for linking all those items, especially ones in my budget. If I had your legs, I would wear shorts all summer : ) Maybe the looser boyfriend shorts would work for me though. I love your effortlessly cool style.

  13. Karly says:

    These are the perfect pair of boyfriend shorts – definitely going to check them out!

  14. Hahaha Gator fans wear jorts! One of my fave SEC memes. I love my boyfriend shorts (I have two pairs!) and style them just like that. I love those shoes! I am on the hunt for a white pair and those Target ones are sold out!

  15. umm can we say legs for days?! so so cute!

  16. Chesson @ A Southern Twenty-Five says:

    I don’t know how the UF fans wear jorts thing started, but you’re right, you hear it everywhere in reference to the Gators! You totally rock these boyfriend shorts those (& those wedges!)

  17. Ashley says:

    Love these boyfriend shorts on you, lady! I’m a total denim shorts FIEND in the summer- can’t get enough! Right or wrong. :)

    Le Stylo Rouge

  18. Maegen says:

    Shorts with wedges is like my favorite style ever! It can make any woman’s legs look long and lean! I love this whole look – you look effortlessly beautiful!

  19. I’m loving this relaxed look!! I’m so ready for warm weather!

    xx Chelsea

  20. Hopefully once the squat challenge is done I’ll be boyfriend shorts ready this season! ;)

  21. I’m not a fan of shorts, but these look great on you! The sandals are perfection!
    xo, Lily
    Beauty With Lily

  22. Literally laughing out loud at, “There is no festival going on, just stop with the mom shorts”. I couldn’t agree with you more, it’s SUCH a bad look on everyone! I do however love your boyfriend shorts, I definitely need to get a pair!

  23. These are super cute on you! And YES please oh please stop with the mom shorts, they look awful even when a festival is going on. Just NO! :-P
    Green Fashionista

  24. This outfit is super cute on you!! I have really always had a hard time with shorts because my legs are so dang long! I’m almost 5’10 and have a tiny waist, so shorts look SOOOO itty bitty on me, these might work just well ;)

    Thanks girl! Keep inspiring!


  25. Yup. Love these shorts. Love shorts. So great for active mama lifestyle and these are stylish enough to not feel frumpy!

  26. Amanda says:

    I love this outfit, it’s perfect for Summer here too!

  27. Nikki says:

    I love a good pair of boyfriend shorts, the length on them is appropriate and they are more comfy!

  28. I love boyfriend shorts so much! For almost being in my 30s, there’s no way that I could (or would want) to wear booty shorts. Boyfriend shorts are perfect!

  29. Jill says:

    I need to get a pair of distressed boyfriend shorts ASAP! This is such a stylish look!

    Doused In Pink

  30. Such perfect casual style for spring and summer!! Love the wedges with the shorts!

    All the Cute ?
    Today’s Post: Boho Joggers

  31. Pinky says:

    Thank you for calling out the mom shorts, that trend needs to go away, NOW!

    What a funny SEC insult, makes me laugh a lil bit. You are rocking this look!

  32. Jaelan says:

    I’ve said it before, but I’ll say it again – I really like how you’re branching out. You look great in sleek, sexy looks… but it’s so much more relatable to me to see you in something like this. :) I’m selfish so I like seeing these things. Haha. That tee looks amazing.

  33. Kelly K says:

    You look so adorable! Those are the perfect boyfriend shorts and I love those wedges! Such an effortless look!

  34. Jessica says:

    Loving those shorts and the longer cardigan!

  35. Courtney B says:

    I tend to stay away from “boyfriend” anything when it comes to bottoms… I feel like I can’t rock the shape of them. (I also feel like I can’t rock anything right now while I’m still in the process of getting my post baby body back in shape, ha!) But I love these shorts on you!

  36. Darcy says:

    Everyone needs a good pair of denim shorts! Love this!

  37. Kelsey says:

    Love this look on you!! I definitely like wearing wedges with shorts because it makes me feel like my legs look longer & leander!

  38. Alice says:

    Loving the way you pull off these boyfriend shorts, and I’m obsessed with your necklace!

    xo, alice / T Y P E N U

  39. Don’t take this the wrong way, but this is totally momsemble approved! I love looking cute and wearing flirty skirts and dresses as much as the next gal, but chasing a toddler in a dress has it’s troubles. You have to wear biker shorts or spanx underneath to avoid… well…. you know. haha. I could look cute in this and save my child from whatever moment of impending doom about to happen to them with ease! (;

  40. kristen says:

    i am still searching for the perfect pair of denim shorts. i’m not that tall but for some reason, normal length shorts look like booty shorts on me. must be that booty of mine, lol.

  41. Paula says:

    Love this outfit! The shorts are so cute. Now, where in New Jersey can I find a gorgeous wall like this one?? :D:D

    Thirteen Thoughts

  42. Rachel says:

    I absolutely love this outfit! I’m definitely a fan of the longer/boyfriend shorts vs. the short short ones!

  43. Amy Arnold says:

    I love these shorts on you! I ordered them and ended up sending them back. They didn’t look as cute on me. ;) Love the wedges too.

    Amy Ann
    Straight A Style

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