4 Foolproof Ways To Style Long, Denim Shorts


A couple of weeks ago, I did a huge try-on of long denim shorts — dare I call them Bermuda shorts? As it turns out, there were a couple of pairs that I liked. So for the purposes of “research,” I started playing around, trying to figure out a few summer outfit ideas for long denim shorts.

In summary? It’s tricky, folks.

But the advantage of the longer short length is that it is pretty dang comfortable. I can sit without anything leaving marks on the backs of my thighs, or worrying about scratchy grass when hanging with my kids at the park.

4 Summer Outfit Ideas For Long (Bermuda?) Denim Shorts

So. Here are a four outfit ideas featuring long denim shorts. These outfit formulas are so foolproof, they’ll work with any pair (and they’re fully tested with two verrrrry different pairs of long denim shorts).

Bye-Bye, Denim Underwear… Long Jean Shorts Are IN — These 2 Are My Fave

1. Pistola High-Rise Distressed Denim Shorts – light wash, slight distressing. They’re super-soft (but not stretchy). Fit is TTS (I’m wearing a size 27).

2. Anine Bing Gavin Wide-Leg Denim Shorts – dark wash, REALLY long. These are basically gauchos. Ripped waistband, fit is TTS (wearing a 27). In the video, I mention that I might shorten them a bit. Nope. They’re still long, and I’m just leaning into that skater vibe.

Other Pieces Featured In The Video

Outfit 1

J.Crew Baird Linen Shirt (M) – Mike’s linen shirt, the one so drapey and delicious I love to steal it.

Naturalizer Heels – I’ve been wearing this style of heel since…2003? Good grief. Love the minimalist vibe and the fact that they’re both comfortable and walkable.

Clare V. Clutch – The colors are constantly changing, but these little fold-over clutches from Clare V. can hold a decent amount of stuff. I love mine.

Outfit 2

FRAME Keyhole Tank Top (eBay) – My FRAME silk tank is old, but I was able to find a bunch of them on eBay! I’m wearing a size small.

The Drop Knotted Handle Bag – This bag is really cute and under $50.

Loeffler Randall Slide Sandals – These heels are so unapologetically girly, with a low, walkable heel. I get a ton of use out of these.

Argento Vivo Hoop Earrings – If earrings bug you [S raises hand]…these are for you. They’re so weightless; this is one of the few pairs of earrings I can happily wear all day.

Outfit 3

Anine Bing Vintage T-Shirt (similar) – My Anine Bing tee is old, but the one linked fits exactly the same. My most-worn tee (wearing a size small).

Clare V. Crossbody Bag – I love this thing, so annoying that it is constantly sold out. This Senreve bag is similar, and Banana Republic also has a similar belt bag (looks smaller, though).

Brother Vellies Huarache Flats – These have been such a fun, unexpected little win. They literally elevate every outfit. I bought mine over a year ago, so they’re no longer in stock, but these Nisolo Huarache Flats have almost a thousand glowing reviews, and look similar.

Outfit 4

Hanro V-Neck Camisole (S) – I’ve been wearing these simple black tank tops since 1998. No joke. They’re my most-worn piece EVER.

Vince Crochet Sweater (S) – Annoyingly expensive, but I’ve found it’s a perfect piece to pop on when I just need a little something, even though it’s hot. For a more affordable option, try — WOW! — this Old Navy crochet sweater. Dang, that’s good.

Vans Classic Sneakers – I’m a Vans girl. Always have been, always will be. (I just ordered their new “Comfort Cush” version to try… will report back.)

Clare V. Woven Bag – I’ve been wearing this bag for years. I’ve gotten so much use out of this poor bag, I ended up (finally) doing a full review. It comes back into stock sometimes, but is proving harder to get. I just came across this Kayu straw bag at Revolve and it looks like it has a very similar vibe.


Oh hey, Pinners! This one’s for you…

It's official: I'm putting down the denim underwear for these 2 pairs of long denim shorts. These 4 summer outfit formulas are so on point, they'll work with any pair (+ they're fully tested). Watch.
It's official: I'm putting down the denim underwear for these 2 pairs of long denim shorts. These 4 summer outfit formulas are so on point, they'll work with any pair (+ they're fully tested). Watch.

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