My Favorite Summer Shorts

So we all know how much you guys like Dressing Room Diaries (I do, too!), but I wanted to do a post solely dedicated to all the pairs of shorts that I absolutely love! Ones that left the store with me every single time, fit like a dream and keep me coming back for more, reaching for them each and every time I look toward the shorts section of my closet.

I’ll be the first to admit that shorts are a dicey category for me. In the summer I often opt for dresses instead for two reasons:

1. I have more of them, so it just seems easier

2. Shorts and I have a love/hate relationship. I have muscular legs, but a smaller waist, so typically what fits my waist doesn’t fit my legs. The phrase “sausage casing” comes to mind…and yeah – no thank you.

But in an effort to maybe help any other girl out there who also suffers from this – I wanted to break down what works for me! These are all Kait tested, approved and purchased.

J. Crew Factory Pull On Shorts – They have an elastic waistband and still look chic! I have them in several colors and prints and almost every time I wear them someone asks where they are from! Not the best photos below, but here they are on. They constantly have new colors, prints and styles so keep your eyes peeled! I have them in size 4 and they fit really well. Printed version here.

J. Crew Factory Scallop Hem Shorts – I was shocked by how much I liked these, considering I ordered them online without being able to try them on. I ordered a size 6 and while the waistband is slightly large, I LOVE how they fit on my legs. Plus, they come in seriously awesome colors.

My Favorite Summer Shorts - the pairs I reach for every single time, plus sizing information! - CommuniKait

J. Crew Factory Printed Chino Shorts – I have been wearing these printed shorts for years. Each summer, they come out with a few new prints and I try to snatch up a pair or two every time. This summer was especially awesome, because they had an Oahu print! I wear a size 6 in these and they are comfortable. The inseam is really short in these so I need that extra space for my legs!

My Favorite Summer Shorts - the pairs I reach for every single time, plus sizing information! - CommuniKait

Levi’s 501 Denim Shorts – Are these shorts I would wear to a family function? No. But honestly – they are my absolute favorites for a day at the beach or a casual day at home. They’re comfortable and the denim is soft. I did cut the sides to make them a bit more roomy, but the denim itself already had a distressed look to it, so it just added to the appeal for me, honestly. I wear a size 29 and they have lasted me 4 summers!

My Favorite Summer Shorts - the pairs I reach for every single time, plus sizing information! - CommuniKait

Levi’s High Rise Shorts – These are my go-to denim shorts for everyday wear. The are comfortable, the cuff gives them a clean/more polished look and they are perfect for shorter tops since the rise is so high! I wear a 29 in these as well.

My Favorite Summer Shorts - the pairs I reach for every single time, plus sizing information! - CommuniKait

And if I’m not wearing any of the above, you can 100% find me in gym shorts. My favorites are here, here and here. Whether you’re working out or exploring, they can’t be beat for fit, wicking or comfort!

My Favorite Summer Shorts - the pairs I reach for every single time, plus sizing information! - CommuniKait

Pictured above: Lululemon Speed Short

Now, tell me what your favorite summer styles are! I’m always on the hunt for more options, so feel free to drop links below 🙂

June 23, 2017


  • I do not love shorts on me either – why do I like my body in pants but hate it in shorts?! Usually it’s just better to opt for a dress if your brain is going to do that to you! But the 2 pairs I do own are from JCrew Factory, which seems to be the only place I can find something I kind of like. The scalloped ones really are great – maybe something about that scallop shape distracts my eye in a way that makes me think they’re way better than regular shorts? And I sometimes want to be the kind of cool person who wears denim shorts… if you’ve had luck with those particular ones, I may have to give them a shot!

    • Kait

      Isn’t it weird that we can be totally fine in pants…even white pants (?!), but when it comes to shorts we are like…eh – no thank you! The scallops are SO fun and I would highly recommend them. I’m kind of bummed I didn’t get them in more colors, but ah well. And you can’t go wrong with denim!

  • Okay I’m buying those Levi’s!

    • Kait

      You won’t be disappointed!

  • Love Levi’s for just about everything, they are the brand that loves short girls. HAHA! I haven’t bought shorts from J.Crew Factory before, but I am heading over to their site now!!

    • Kait

      Tell me what you order! And special thanks to YOU I am now a believer that overalls might be a thing for me. Stay tuned!

  • Jen

    I have such a rough time finding shorts! The only places I’ve had true success are GAP and Target, the fit of their shorts has always been the best for me.

    • Kait

      Oh GAP is a good one! I’ve never tried them on at Target before, but someone else mentioned there too! Now I need to track some down…

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  • I pretty much live in shorts during the summer but yes, they are tough to shop for! I do have to say that I am so glad for this post because I feel like my legs are pretty similar to yours, haha. I’ve never tried J. Crew before but I love those linen shorts! They look so comfy! I have had some pretty good luck with Old Navy shorts, especially the boyfriend ones they released this year.

    • Kait

      Oh I need to look into Old Navy! I think I have it my head that they don’t fit me that well since about a hundred years ago I tried a pair on and it ended poorly – so weird how stuff sticks in your mind! I will check them out next time I’m at the mall. THANK YOU! 🙂