4 Different Ways To Roll Your Boyfriend Jeans

valentino white sneakers

Recently, boyfriend jeans are my favorite style of jeans. I love skinnies, but sometimes after a big meal or when you are a little bloated (we all have those days, don’t we?) they are not the most comfortable to wear. I love them, not just because I think they are cute and stylish, but also because they are comfortable, multi-seasonal, and you can wear them dressed up or dressed down as your style and imagination allows you.

Most of us roll our boyfriend jeans when we wear them, but is there only one way to roll your boyfriend jeans? I have recently discovered the answer is NO, so for this post I decided to show you 4 different ways to roll your jeans depending on the type of shoes you are wearing. So let’s get started!

In the first picture, I am wearing my favorite pair of Rag and Bone booties, which hit below the ankle and fit closer to the ankle to give off a more fitted look. In cases like these, keep your roll tight and skinny. If you roll your jeans too high, it will shorten your leg and give you a stumpy appearance–and who wants to look stumpy?

In the second picture, I am wearing my Valentino studded sneakers (which I love, but Dustin is not a big fan haha). He says they are not very feminine, but that is exactly the look I am going for: “tomboy”–sorry love :). In this case, keep in theme with the “tomboy look” and fold your jeans about 1-1.5 inches high. Make sure you fold your jeans (don’t just roll them).

In the last picture, I am wearing my Manolo black pumps on one foot and my studded copper Valentinos in the other. I promise I never go out wearing different shoes, it’s just for the post (ha!). In this scenario, you can rock your boyfriend jeans in two ways:

OPTION A: Start with a small fold followed by a small skinny roll. Keep the fold/roll combo tight and slightly above the ankle bone.

OPTION B: Pinch your denim so they are pulled tightly behind your achilles, then twist and tuck under the pinched denim. You want to give the appearance of a fitted jean around the ankle, but looser around the calf (this is how I did it with my Manolos).

Oh! And just a quick update on my pregnancy…I am now 25 weeks and feeling more and more like an oompa loompa so if you have recommendations on maternity boyfriend jeans, I would love to hear them.

Thanks for stopping by and I hope you enjoyed the post! Also, thank you to my dear friend and stylist, Julie Tuchin, for showing me these amazing tips!

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  1. February 24, 2016 / 5:04 pm

    Love the pics and especially the multiple Valentinos. It’s okay if Dustin isn’t a fan – we think they’re AMAZING! 🙂

    • February 24, 2016 / 5:52 pm

      Nadia!!!!!! Long time no see! thank for stopping by the blog. Where are you living now?

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