How to Style Long Shorts

If you aren’t a shorts person – this post is for you! Say goodbye to super short, tight, low-rise shorts and hello to longer, relaxed shorts. In today’s post, I’m sharing how to style long shorts. And don’t worry, if you aren’t a fan of longer denim shorts, I’ve got other options for you!

Denim Bermuda Shorts Outfits

The rise of the Bermuda-style short means we no longer have to worry about our butt cheeks hanging out. Woohoo! Whether you call these long denim shorts, mom shorts, or bermuda shorts, they don’t have to look frumpy with the right styling.

Long Denim SHorts with an Oversized Blazer Outfit

I’m starting out with my favorite shorts outfit at the moment – relaxed denim shorts with and an oversized blazer. This just feels so effortlessly cool to me. Not to mention, comfortable!

This outfit is simple at its core; I’m wearing a tank top and casual denim shorts. However, a good outfit is all about how you style it. I added an oversized linen blazer to elevate the look. The linen material gives the blazer a more casual feel, which complements the denim shorts nicely. The belt adds a polished touch to the outfit. My checkered bag ties in the black from the belt with the natural tan texture of the linen blazer. Finally, the strappy heels complete the look. The short heel adds a dressy element while still being casual enough for daytime wear.

* Styling Tip: To make your legs appear longer when wearing longer shorts, opt for visually lightweight footwear. My strappy heels reveal a lot of skin and do not segment my leg with heavy straps. Additionally, steer clear of shoes with ankle straps, as they can interrupt the continuous line of your leg.

Long denim shorts with oversized blazer outfit

Long Denim Shorts with Feminine Top Outfit

Another option for styling long denim shorts is to pair them with a feminine top. This contrasts nicely with the slightly more masculine cut of the shorts. Granted, my top is also boxy, but the ruffles, puff sleeves, and delicate details are definitely feminine. If you are uncomfortable with a loose top and loose shorts, you can add a feminine tank—like this one that you’ll see below.

To finish the look, I added feminine silver flats (which act as a more interesting neutral) and a classic bag. I loved how the bag’s denim blue shade matched my shorts and blue floral top, giving my outfit a monochromatic look.

Citizens of Humanity Ayla Shorts with Doen Henri Top

How to style long denim shorts for summer

Outfit Details: DOEN Top | CoH Shorts | Sezane Bag | Freda Salvador Flats – 15% off code 10JESSICA

Mom Shorts with Vest Outfit

This outfit is from a few years ago but I still like the elements of this look. It’s still on-trend to style long shorts with a fitted vest. I would probably just update the vest with a cutaway linen vest.

And I know I said that you shouldn’t wear shoes that cut off your leg. But the cowboy boots are more of a trendy style choice where I wasn’t really worried about proportions. However, my boots are a tan shade that blends into my legs better.

Mom jean shorts with linen vest and cowboy boots

Outfit Details: Dissh Vest (Try this instead!) | Madewell Shorts (similar) | Sezane Boots | Clare V. Bag

Tailored Shorts

If denim isn’t your thing, tailored shorts are a great option. The shorts I’m sharing below are less casual than denim but are just as comfortable.

Drapey Shorts with Elevated Tank Top

These shorts are a mix of lyocell and cotton, which gives them a drapey feel while still being polished. With a matching blazer, drapey tank, and a change of shoes, this look could potentially be appropriate for a casual office. (Don’t quote me though, I’ve never worked in an office!).

Shorts outfit ideas for summer: Tailored Shorts outfit

Sezane Ron Top Outfit with Everlane Tailored Shorts

Outfit Details: Sezane Top || Everlane Shorts (similar) || Sezane Sandals (similar) || Sezane Bag || Maison Miette Scarf

Since I don’t have anywhere fancy to go, I went with a light knit tank and strappy sandals. Even though these shorts aren’t super long (the inseam is 5 1/2 inches) I still prefer the look of a light, strappy sandal.

*Style Tip: Don’t be afraid to mix browns and blacks! All-black or all-brown accessories can sometimes look too matchy-matchy. I really like the chocolate brown shoes and bag with the black and white outfit. The silk scarf tied on the bag brings some of the black onto the bag, which ties the whole thing together!

Cotton Trouser Shorts with Knit Tank

Because of the longer length and pinstripes, these tailored cotton shorts give more of a trouser vibe than the drapey shorts, in my opinion. But that doesn’t mean they can’t be styled casually! Instead of a blouse or blazer, I paired these shorts with a feminine knit tank. It appears I have a thing for knit tanks! I like to incorporate different textures and fabrics in my outfits when I can.

Sezane Alfred shorts with Giselle Top: shorts outfit ideas for summer

Outfit Details: Sezane Tank || Sezane Shorts || Sezans Sandals (similar) || Sezane Bag || Sezane Belt

Matching Shorts Sets

If you want a well-put-together summer shorts outfit, matching shorts sets are a no-brainer! Sometimes, brands make your life easy by offering a matching top and bottom. That way, you don’t have to worry about making sure colors, patterns, or styles match.

Casual Matching Shorts Set

I got this matching set from Darling and it turned out to be a summer favorite. It’s made from a light, drapey fabric that makes it easy to play or rest in this look. The shorts have an elastic waistband which make them EXTRA comfortable. And the matching top is perfectly cropped with pockets and side slits.

This exact set is still available and on sale!

Matching olive green shorts set; shorts outfit ideas for summer

Outfit Details: Darling Top || Darling Shorts || Clare V. Bag || Jenni Kayne Sandals

Lounge-wear Matching Shorts Set

I got this matching lounge-wear set from the sleepwear brand, Lunya. Technically, this set can be worn as pajamas or lounge wear but I prefer to wear it out! This set is especially perfect for vacation or travel. The cotton material is SO soft and easy to wear. You can wear it with the shirt buttoned up, but I prefer to wear a tank underneath because it looks less like a pajama set to me.

This set gives off a sporty vibe so I chose to wear my “sporty” sandals. I wore this set on vacation with sneakers and a belt bag and I actually preferred that look!

Shorts Outfit Ideas for Summer: Lunya Matching loungewear set

Outfit Details: Lunya Top || Lunya Shorts || Sezane Tank

Matching Trouser Shorts Set

Another matching set from Darling! This time I switched up the shirt for a matching knit. Again, I like this combo because it’s matching without being to matchy (if that makes sense). Instead of a button-up shirt in the same cotton/linen material, I went with (another) knit tank! This tank has a nice texture due to the open knit design. That also helps keep everything breezy!

Outfit Details: Darling Tank || Darling Shorts || Sezane Bag

I hope this post helped you figure out how to style long shorts! I know we’re nearing the end of summer but don’t put those shorts away yet! I’ll update my blog soon with How to Style Long Shorts for Fall!