My Style

Upgrade your summer shorts: from casual to dressy!

It’s time for some seasonal closet — and outfit — revamping, this time with shorts.

Summer shorts have become a staple in my wardrobe. They’re a great basic piece, usually easy to care for, and, most importantly, they’re versatile! You’ll typically see me sporting a pair of shorts as part of a casual, usually daytime, outfit. I throw on a simple t-shirt, grab a tote bag, slip on a pair of sandals, and I’m good to go!

This classic pair of black shorts really does the trick most of the time.

casual shorts outfitStriped v-neck tee: Old Navy // Black chino shorts: J.Crew (similar) // Black and white tote bag: J.Crew (previous season,similar here) //Black flip flops: Target (similar)

Why not upgrade that look for the evening? A quick change of shoes and accessories can easily take shorts from daytime to nighttime. I’ve shown a few outfits where I’ve paired shorts with heels before, but never really explained WHY they are such a great style revamp from casual to dressy.
casual and dressy shorts

One advantage of wearing shorts: leg transformation! Let’s take a look at the side by side comparison above. Adding a heel instead of wearing a flat sandal or a flip-flop instantly elongates the legs. Think about it: you gain a few inches of leg when your heel is elevated and the top of your foot is showing! It’s an instant calf-enhancer, too.

Once you’ve put on the heels, swap out your daytime tote for a fun envelope clutch, switch the plain tee for a dressier top, and take that up a notch with a statement necklace. Your shorts — and you — are ready for a night out!
dressy shorts outfit

Striped tank: LOFT (similar ) // Black chino shorts: J.Crew (similar) // Leopard print pumps: Ivanka Trump Pinkish (same shoe, different colors here) // Envelope clutch: ASOS (similar) // Scene Stealer necklace: Jewelmint

Another amazing advantage of shorts for me is the ability to wear a cropped hemline and not feel self-conscious. I would likely never wear a mini-skirt or a dress with the same hemline as these shorts. I would almost certainly be self-conscious the entire evening, fearing a potential fashion disaster. Not with shorts! I can rest easy knowing that I can lean over, sit down, and get in/out of a car without any accidental over-exposure.

So, the next time you are thinking about getting dressed up for an evening out, consider glamming up your casual shorts look.

Do you wear shorts? Have you worn them with heels? Would you give it a shot?

This post is part of BlogHer’s Revamp Your Style editorial series, made possible by Schick Hydro Silk.


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  • I’d consider wearing shorts with heels, but never to work. I’m old school in that proper work attire means no shorts or bare legs (hose/tights). Every office I’ve worked in said no to shorts and bare legs. And shorts with tights or hose would just look goofy! Lol

    That is a really cute outfit though. Like all your outfits. I like that you shop at stores I have access to (small town).

    • Oh yeah, I definitely wouldn’t be wearing that outfit in a work environment…just if I was going out for the evening and such! Thankfully, I haven’t experienced any work places that don’t allow bare legs if you’re wearing a dress or skirt that is knee length. I can’t imagine wearing hosiery here in the Florida humidity!

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