Yesterday, I shared my most recent Trunk Club. I had requested a summer refresh and kept these J. Crew sailor shorts. I love the preppy, fresh, summer vibes so much! Today, I’m sharing how I’ve been styling sailor shorts. Let me know how you would wear them!

Top: old // Shorts: J. Crew via Trunk Club // Flip Flops: Jack Rogers
This is definitely my favorite way to wear these shorts. I always feel comfortable in a button-up. so this is my go-to when I don’t want to think too hard about what I’m wearing. I would actually prefer a more bleached and distressed button-up for these shorts, but this is the lightest chambray I have. Side note: I usually have dress tape to close the gap in my button-ups but I had definitely forgotten it this day! (I have the shorts linked below, and they are on sale right now!)
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Top: Everlane // Shorts: J. Crew via Trunk Club // Flip Flops: Jack Rogers
This is the top I wore with the shorts during my try on session on Instastories, and I immediately loved it. I Love how white and blue just pop together. And, yes, technically, the shorts are off-white and blue, but I think it’s perfectly fine to mix the two. I think later in the summer, I will style these more with my Converse shorelines!
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I hope you enjoyed this post about styling sailor shorts. Honestly, I feel a little bit out of my comfort zone because I rarely wear shorts. I know the more I get out of ‘box,’ I’ll discover more ways that I like to wear them.