Styling Tips: How To Wear Boyfriend Denim

There is no denying my love of a good boyfriend jean, and I'm pretty sure I've mentioned it before but I've been rocking the look since 7th grade when I stole my dad's perfectly worn-in Levi's and wore them to school on a weekly basis.  Looking back, I realize I have a history of going a little quirky with my choices here and there.  It's what makes personal style fun, putting your own stamp on things and not just wearing what you think you are supposed to wear.  While boyfriend denim is certainly a trend now, there are so many different ways to wear them that they don't feel tired yet.  Some argue they aren't particularly figure-flattering, but I think the whole point of them is to give off that slightly oversize disheveled look.  Personally I love to dress in items that give a bit of wiggle room, if things get too tight or structured I feel uncomfortable.  It really is all about balance, and again how you feel comfortable wearing things.  Below I have collected a handful of ideas on how to style a pair of boyfriend denim, and if you can believe this is only the tip of the iceberg.  I had to edit way down, and yet still feel like I am throwing a lot at you!  

Images: 1/2/3/4/5/6/7/8/9/10/11

There certainly is a little bit for everyone here, and it really is as simple as mixing and matching what you like to come up with your perfect combo!  Let's flush out the basic components below...

Start with the perfect pair of boyfriend denim, then...

1. Pair with a blazer

2. Wear a slouchy tee

3. Top it off with a long, feminine coat.

4. Under the blazer, or alone, wear a graphic or striped tee.

5. Pick your perfect pair of shoes:

Don't forget the fun finishing touches such as tousled hair or a big messy bun, some chic shades and the perfect swipe of lipstick!  So tell me, which combo feels the most "you"?  I really love a boyfriend denim paired with heels and a striped or slouchy tee, and some fun statement jewelry!


  1. This is amazing inspiration! I love it all... I have to wait probably another month or so for it to warm up enough to let my ankles back out bare. It's been SO SO cold here this week (although last week was mild). I definitely love the boyfriends with flats for everyday and the boyfriends with heels when I am feeling extra sassy! :)

    1. It's been super cold here too! Def can't wait for a warm up!

  2. I love this handy little chart for options to pair with boyfriend jeans... They're not quite in my style comfort zone at the moment because I'm so used to more fitted bottoms, but I would like to branch out and make them be! Helps to have specific ideas for outfits when I'm starting from a slightly unsure place.

    1. Glad you like it Anne! I think boyfriends are so cute on petites-you could totally rock them!

  3. Great tips! I adore boyfriend jeans, I have a cord pair and a denim pair and I find they are so much more versatile than I had originally thought.

    xoxo Bree
    The Urban Umbrella

  4. I'm obsessed with boyfriend jeans! They're one of my favorite fashion staples!