Fashion Crush – Dressy Shorts

Dressy shorts can take the place of skirts or dresses easily in the summer. Come see how to make them work in your wardobe!

dressy shorts white sweater cute summer style outfit

Honestly, is this not the cutest?! Via Lovely Pepa.


Dressy shorts. A contradiction in terms, right? However, I have seen them more and more in the last few years, and I must say, I’m a convert!

Previously, I always thought of shorts as casual, and I really only wore them with a sandal, flip flops, or Converse sneakers. However, dressy shorts worn out at night with heels can be such a cute look!

I admit, I am not a skirt wearing person for the most part, so I guess they speak to me. They are short (like a skirt) but way, way more comfortable. And sexier!

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dressy shorts with sweater cute summer street styleHere she’s wearing flats, but the whole outfit is elevated way beyond the average cut-offs and tee. Via J.Crew.

They look great with a blouse, a blazer or a loose tank top. Heels are the way to go if it’s an evening out, but for a dressy lunch or day event, they are really cute with flats as well.

I think they are a great option when you are not sure how dressy an event will be and you are torn between a dress and pants.


dressy shorts black and black blouse red carpet summer fashion ali larterAli Larter at a red carpet event. This is the outfit that sold me on dressy shorts! Via Pop Sugar.


Obviously, they are not appropriate for some events (a wedding is one that comes to mind) but for dinners out, drinks with friends, or a summer party, I think they are a great choice. I’m even seeing them on the red carpet!


dressy shorts grey with blazer and heels charlize theron red carpet fashionCharlize Theron at another red carpet event! Via Fandango.


dressy shorts black with white blazer graphic top sunglasses summer street styleVia Damsel in Dior.


dressy shorts black with jacket olivia palermo summer styleOlivia Palermo looking gorgeous, as always! Via Who What Wear.
dressy shorts bermudas off the shoulder top hat gorgeous summer street styleHere is a longer Bermuda style short worn with an adorable summer top and heels, and it looks amazing! Via Walk in Wonderland.


And for those of you who aren’t comfortable in shorts, just go a little longer. Knee length or almost-to-the-knee shorts are adorable with heels, and no different than a skirt – only cuter!


dressy shorts leopard with white top olivia palermo summer street style chic Love these leopard shorts! Via Olivia Palermo.


cute dressy shorts outfit pink shorts black heels and white top street style summer fashion
Could there be a cuter summer evening outfit than this?! Via


Shop Dressy Shorts 

Happy Friday!
If you enjoyed this post, be sure to check out more fashion inspiration below: 

French Style Fashion Essentials for Spring/Summer

Summer Fashion Fave: Charming Straw Bags

Fashion Fave: Always Versatile Striped Tees!


dressy shorts graphic on Maison de Cinq

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  1. You are always so inspiring, Sheila! I don't usually think of shorts as being dressy but I love these examples. Maybe I will try a few of these combinations. Enjoy your weekend!