Rolled Denim Boyfriend Shorts: Day to Night

Every year around this time, I start getting tons of questions about shorts and my best recommendations for shorts for women over 40. Over the past few years, I’ve tried hundreds of pairs of denim shorts… okay, maybe it’s in the tens, not the hundreds, but still. It’s a lot!

Women have different bodies and different comfort levels, so our needs are different, but every once in a while I find a pair of shorts that is super versatile and works for many body types. This year, that pair is the Caslon rolled denim boyfriend shorts.

When I got out of the car to shoot this look, Alison (my photographer) immediately asked where these shorts are from. She couldn’t believe it when I told her they’re one of the Nordstrom made brands.

Nordstrom made brands give you a lot of bang for your buck because you get the quality and style that Nordstrom is known for, without the markup that often comes with the big name designers.

These shorts have just a bit of fading and whiskering to keep them casual, but they don’t have any rips or tears, and the boyfriend cut gives them the perfect amount of slouch. They’re soft and comfortable, and with the cuff, they have a 4″ inseam and a comfortable 9″ rise. I definitely recommend sizing down, as suggested on the website. I’m wearing the 27.

I kept it simple for this post and paired these shorts with a plain white tee — also the Caslon brand. The combination of denim and white never gets old, especially in the spring/summer.

This tee is only $19, and it comes in tons of solid colors and some prints as well. I buy a new white one every year, and I also have it in a few prints. It runs a little big, but I always get my usual size small so I can throw it into the dryer.

And this crossbody is one I’ve shared before, but here I have it unzipped on the bottom so you can see better how it expands. It appears that the grey is sold out, but the tan is a really good year-round color as well.

And finally, how fun are these sandals!?! Look, Mom! I’m wearing a color on my feet!

Okay, so the yellow is pretty muted, but still. It’s not a neutral, and I love how the sunshine yellow plays off the white and denim in the rest of the outfit.

These minimalist two-strap sandals are right on trend this season, and I like how the espadrille-inspired braiding highlights the platform sole. Treasure & Bond is another Nordstrom made brand, and when you buy Treasure & Bond, Nordstrom donates 2.5% of net sales to organizations that work to empower youth.

I sized down a half size in these sandals, as I usually do in slides, and they just fit. For most ladies, I would say they will be true to size, but you may want to size down half if you have narrow feet.

I also picked up this French terry hoodie in the nautical navy and white stripe to throw on with shorts on those chilly summer evenings. Of course, it will also work with jeans or pants as well.

It’s lightweight with a relaxed fit, so you could size down if you wanted a closer fit, but I went with my usual size small for a little more slouch.

I swapped shoes for this outfit, into another pair of minimalist two-strap slide sandals. I didn’t even notice the similarities until I started writing this post!

These BP. sandals are surprisingly comfortable, and they’re a great price. The footbed is soft and has some shape to it, and I was able to walk easily in them. I wore them home from this shoot and kept them on for the rest of the day.

I like how they almost disappear on the foot, which elongates the leg, but the silver studs add a nice detail. The silver rhinestone or tan leopard rhinestone would be cute too, and there are a few solid color options as well. I also sized down to a 7.5 in these.

I accessorized both of these outfits with the Halogen brushed teardrop earrings — they have a great casual-cool vibe that works well with these laidback looks. And I’m wearing my trusty Maui Jim sunnies.

As always, when you shop at Nordstrom, you get their free shipping and free returns. And don’t forget about their BOPUS (Buy Online Pick Up in Store) and contactless curbside pickup options.

And if you aren’t already a Nordy Club member, be sure to sign up so you can start earning points toward Nordstrom Notes when you shop. You also get to enjoy exclusive perks like members-only access to sales, offers, and events — like the Nordstrom Anniversary Sale, which is just around the corner!!!

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photos: Alison Cornell

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17 Responses

  1. I need another pair of denim shorts like I need more booties, lol, but I ordered these as I usually order one new pair a year and donate or toss a pair. And I’m loving the color on your feet, Jo-Lynne! I laughed when I saw the pic because last week I bought a pair of pale lime shoes in a similar style. I was thinking they would be fun with jeans or jean shorts or even my jean skirt and a white top.

  2. You look great in this outfit! I really like both pair of sandals. If the BP pair had arch support, I’d be all over them. I recently got a white tee from ON that I like, but it is a little on the thin side. I’d like to get one that is a little less see through. I hope that you have a great day!

  3. You look great, but I have found that cuffed shorts are not flattering on me. The cuff visually cuts me off.

  4. Very cute. Does the cuff turn down or is it sewn? 4″ is too short for my legs. I need 6-7 inches. Sometimes cuffed shorts work if I can get an extra 2 inches. Thanks

    1. Gina, the KUT from the Kloth Catherine boyfriend shorts JoLynne featured last summer are 7 inches cuffed and have been perfect for me. Just bought a second pair this week in a lighter wash, too.

  5. I recently ordered the Caslon Cotton Twill Shorts, can not wait to try them on- NOW, I will have to check these denim ones out as well,lol.

  6. Shorts are always so hard for me. You are right, we all are so different with comfort levels and fit when it comes to shorts. I never have felt comfortable in shorts as it seems hard to find the right length and fit on the leg. Now that I’m older, I prefer casual dresses. I like these shorts but may be too short for me. Very cute outfit and I love the navy striped hoodie. You’ll get lots of use out of that. I have exciting news. My son, my youngest of 3 and his wife just had a baby girl last night. Its my 3rd grandchild now in a year and a half. They are coming fast now. She’s so sweet and I can’t wait until we can go see her. With covid rules, no one allowed in the hospital. We live 3 1/2 hrs. away.

  7. This has never happened where I own something before you show it on the blog, but I ordered the Caslon shorts last summer! I didn’t follow the advice and size down, which was a mistake, but I wear a d-ring ribbon belt with them and they still look cute! My only criticism of the shorts is the cuffs don’t lay as nice once they are washed, and need ironing if you want them to look perfect. I don’t bother honestly. I also went ahead and ordered the Wit and Wisdom shorts you linked in the comments as I really want a pair without a cuff and it’s so hard to find the 4 inch inseam. Fingers crossed!

  8. Those shorts look so good on you and right, the perfect pair of denim shorts can be hard to find. But once you find them, they are so versatile.

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