While I’ll happily wear white jeans year-round, white shorts — to me — feel like the ultimate sign of summer. They’re a piece I don’t often bust out until my legs have had a little touch of sun, and they have a carefree, playful vibe — almost devil-may-care.
Am I going to eat this ice cream cone in these white shorts? Yes. Yes I am.
Because I’m wild like that.
Naturally, white shorts, like Sperrys and cable-knit cardigans, tend to skew preppy. And while I’m not opposed to preppy pieces, my personal style is a little messier, a little more tomboy. Definitely more undone.
So when wearing white shorts, I’m always looking for ways to offset their inherent preppiness. And my favorite method, year after year?
Classic, checkered Vans.
sweater (s) | shorts (27) | Vans (‘Comfy Cush’ version) | bag (and similar)
Cute, Casual & Not-Too-Preppy: White Shorts + Vans Slip-Ons For Summer
White shorts and Vans have been the perfect pair to nail that carefree-but-not-too-preppy vibe I’m going for. Even when I pair the combo with otherwise preppy pieces (chunky knit sweaters, a striped tee, for goodness sake) the Vans calm it all down, dahling.
I’ve recently upgraded to Van’s new ‘Comfy Cush’ version of their classic slip-ons, and while that extra bit of cushioning doesn’t feel like a lot, it IS exactly what my aging feet desperately needed. The comfy cush Vans have been a huge improvement over the classic pair.
Summer Outfit 1: White Shorts + Vans + Striped Top

tee (6) | shorts (27) | Vans (‘Comfy Cush’ version) | similar Clare V. (or J.Crew) | watch
I’ve been wearing this old St. James tee, picked up in France in 2016, when we took the kids to Normandy Beach. It’s basically perfect, and I haven’t even bothered looking for a long-sleeve striped tee since. (I also roll the sleeves and wear it short-sleeved as well.)
tee (6) | shorts (27) | similar Clare V. (or J.Crew)
While I’ve owned many pairs of white shorts, this particular pair from FRAME is, perhaps, the most feminine. The rise is a higher rise, and the waistband has interesting detail. The whole result is rather retro, and wildly feminine (even with Vans).
tee (6) | shorts (27) | Vans (‘Comfy Cush’ version) | similar Clare V. (or J.Crew) | watch
Summer Outfit 2: White Shorts + Vans + Chunky Cotton Sweater

sweater (s) | shorts (27) | Vans (‘Comfy Cush’ version) | bag (and similar)
Despite the retro waistband, these cute shorts look good with chunky sweaters, too. This is the outfit most similar to what I wore growing up in Michigan’s Upper Peninsula.
Fun fact: Northern Michigan is one of the preppiest places in the US. I remember coming across an old Washingtonian article, a cheat sheet on preppy style, and was thrilled that Northern Michigan got a shout-out.
It’s true. My summer uniform, growing up, was a seersucker bikini, cut-offs, and a J.Crew rollneck sweater.
Consider this my grown-up version.
sweater (s) | shorts (27) | bag (and similar)
My grown-up version consists of a Jenni Kayne fisherman sweater, but done in 100% cotton instead of cashmere. True to form, it’s perfect, and I especially love the range of interesting neutrals that she does so well.
sweater (s) | shorts (27) | Vans (‘Comfy Cush’ version) | bag (and similar)
Anyone else into the ‘almost preppy’ look? I’d love to hear how you guys are styling your white shorts (or white jeans). If you’d like more ideas…I did an article a few years ago called 5 Ways To Wear White Cut-offs, and I’m still wearing most of those outfit formulas (with a few little tweaks).
xo,
S
photo credits: Redfield Photography
I love everything about this post!
I did get the comfy cush and they are way more comfy than the original slip ons. The only thing I don’t love is the puffy part around the heel/ankle because it makes them look giant. But you make anything look cute Shana, your confidence makes you shine!
Almost preppy is my whole wardrobe. I add in a heavy dose of quirky, colorful and memorable though. I love all of this, and saving the ideas for late spring and fall when we can wear longer sleeves and perhaps a sweater with shorts in VA. It’s going to be kissing 100 for the next 10 days.