How To Wear Distressed Boyfriend Jeans Two Ways

Hi there, lovelies!

I’ve had a few questions lately on how to style certain denim styles, like boyfriend denim, high-waisted denim and gray denim. I’m definitely a visual person and find a lot of inspiration from visual examples, so I thought I’d show you a couple of different ways to style each type over the next few weeks. Fall is coming around the corner and we’ll all be living in denim and leggings so I feel like now is a good time to put together and share this kind of inspiration.’

Please let me know if there is anything else – or any other kinds of denim – you need some help styling and I’ll see what I can do.

Another request that I get is to style multiple items within my closet more than once. So, instead of putting together two completely different outfits for this post I decided to keep the base outfit the same [the top & nd changed things up so you can see the versatility within the base. Does that make sense?

I’ve already shot the looks for gray jeans the same way so please let me know if you like this way of doing these kinds of posts!


So I chose the basics of these two outfits around versatility and budget.

The top is a simple ‘perfect fit’ tee from J.Crew. Every year, they essentially keep the style the same with a flattering fit and the same medium thickness material. This year, though, the sleeves are a bit longer than they have been in the past and the crew neck is a little wider, but not technically a boat neck. There are always multiple colors available, as well.J.Crew runs big so go one size down from your normal. I’m wearing an XXS.

PRICE: $29.99

This pair distressed denim boyfriend jeans are one of my favorite recent purchases. If you’ve been a long-time reader of S&T, you know I have always been a big fan of BlankNYC [or Blank Denim] and they’re coming out with some great quality, affordable pairs of jeans. These run true to size and have a really nice medium wash to them. I also love that they are slightly loose in the leg but not unflatteringly ‘baggy’. The distressing is also not too intense so they can be dressed up without looking trashy, which I’m a huge fan of.

PRICE: $78.00

Here are some other basic options for you if these don’t fit your fancy:

This first outfit is an example of how to dress up distressed boyfriend jeans. Tuck your simple tee in to add a little polish to the ensemble then add a pair of neutral heels, a complimentary handbag and some fun statement earrings … and you’ll be all set!

This is a great option for a late summer night outfit and can transition nicely into Fall by simply adding a lightweight cardigan, which is the perfect segue into the second outfit.

This black cashmere cardigan, these slides and a belt to show off the high-waisted detail of these jeans are just the way to elevate this otherwise casual outfit in a chic way. While some may argue that distressed denim and chic can never be used in the same sentence, I’d like to humbly disagree. Make sure you size up half a size in the slides! They run a bit small.

I hope this was helpful for you guys! Next week, I’ll be sharing three styling options for gray jeans. Similarly to this post, they all have the same base and some items within the outfits have been used multiple times. I hope it sparks some ideas and inspiration for y’all! Stay tuned!

Until then, have a great day! xo.




  1. Kelly R wrote:

    LOVE both looks so much! The loafers and the pop of leopard in the second look are just giving me life!

    Rosy Outlook

    Published 8.9.17 · Reply
    • AlysonHaley wrote:

      Thanks! I love that look too! Really getting into the loafer trend that’s coming back!

      Published 8.9.17 ·
    • AlysonHaley wrote:

      Thank youuu! I love how all the colors came together in that one thanks to print in the clutch 🙂

      Published 8.9.17 ·
  2. La Bijoux Bella | by mia wrote:

    Always love ❤️ the relax and chic look of a boyfriend’ jeans cut … it’s a must have look for the everyday lifestyle! 🙂

    ????????LA BIJOUX BELLA ????????| By Mia | A Creative Lifestyle Blog

    Published 8.9.17 · Reply

    Love the second, casual look!

    Published 8.9.17 · Reply
  4. Morgan wrote:

    I love dressing up my distressed denim!! That second outfit is making me excited for fall weather!

    How 2 Wear It []

    Published 8.9.17 · Reply
  5. Jennifer wrote:

    Love both looks! I’ve always been afraid of boyfriend jeans but I think I might have to try them. Thanks for sharing!

    Effortlessly Sophisticated

    Published 8.9.17 · Reply
  6. That cashmere cardigan look so cozy!!!

    Published 8.9.17 · Reply
  7. Megan Hawksworth wrote:

    I love the way you used the same pieces in different ways — I’d definitely be interested in seeing more of that!

    Published 8.9.17 · Reply
  8. Nicci wrote:

    Such a great post! It shows how much versatility items have and also how to dress up a look that may be considered more casual. I love everything about this!

    Published 8.9.17 · Reply
  9. I love the second look! So perfect for fall. You look comfy but still so stylish!

    Published 8.9.17 · Reply
  10. NataliNataliNataNaNNatali wrote:

    Love the 1st outfit and way to wear the boyfriend jeans! You’re always looking so stylish!

    Published 8.9.17 · Reply
  11. caitlin wrote:

    I LOVE the way these jeans fit and how you styled them – especially the fact that you created two looks out of this outfit.

    So awesome

    Published 8.9.17 · Reply
    • AlysonHaley wrote:

      Thanks, Caitlin! 🙂 xo.

      Published 8.9.17 ·
    • AlysonHaley wrote:

      Thanks Darla!

      Published 8.9.17 ·
  12. Jeany wrote:

    Amazing outfits! I really love both ways of how you styled the distressed boyfriend jeans!
    xx, Jeany from

    Published 8.9.17 · Reply
    • AlysonHaley wrote:

      Thank you so much, Jenny! xo.

      Published 8.9.17 ·
  13. Jess wrote:

    Love this post! I’m really looking forward to more posts where you showcase multiple ways to wear a specific item – I think that’s so helpful! It definitely helps me decide whether or not I’m going to purchase something if I can see the versatility of it! Also loving those bf jeans on you!

    Published 8.9.17 · Reply
  14. TaniaTania wrote:

    Ooo I love the Corbin Slide Loafer on you 🙂

    Published 8.10.17 · Reply
  15. Lindsey wrote:

    Love this post! This made me think of a post I would also love… ways to style denim of different washes (styling light, medium, and dark wash jeans). I struggle with this and find that I kind of give up and throw on darker washes because I don’t know what works with my lighter jeans.

    Published 8.10.17 · Reply
    • AlysonHaley wrote:

      Ohhh okay! That’s good to know! Thanks for the post request! xo.

      Published 8.10.17 ·
  16. Nicole wrote:

    Hello! Just got a pair of Franco Sarto black Mules. Love the trend, but am not sure how the mules should fit. They seem to make a flip flop noise when I walk. Is that how mules should be?

    Published 8.10.17 · Reply
  17. Scotti Krumholz wrote:

    Loved this post with the style options.. I am crazy for that Gucci belt. Can you give some advise on the sizing ? What size are you wearing with what size jeans? I usually wear a 25 in jeans. Thanks for your help.

    Published 8.10.17 · Reply
  18. Nicole wrote:

    Posts I’d love to see!

    How to style different style jeans with differentshoes. Example, boyfriend jeans, skinny jeans, step hem jeans and the shoes that go with them. I’m always at a loss for which shoes go with which jeans based on length of jeans and style and where the jeans should fall in relation to the shoes.

    Published 8.10.17 · Reply
  19. lisaLisa Tran wrote:

    I’ve been curious about boyfriend jeans, but I’m always hesitant since I’m not sure how they’d look on the bum! Maybe in future posts, you can show what it looks like in the back? Ha! That would be so helpful though 🙂

    Love the simple pairings!


    Published 8.11.17 · Reply