Fashion Crush – Dressy Shorts

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 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 sexy!

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.

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! 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 white sweater cute summer style outfit
Honestly, is this not the cutest?! We can’t see her shoes, but I could see a heel with this for dinner out or dressier flats for a lunch date. Via Lovely Pepa.


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. Perfect for walking the streets of Rome or doing some afternoon shopping! Via J.Crew.


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.


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




dressy shorts white jacket red handbag cute street style summer fashion
Cute neutral outfit with the pop of red from the handbag. Via Wendy’s Lookbook.


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! Evidence that the shorts don’t need to be super short to be chic! Via Walk in Wonderland.



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


dressy shorts black with white blouse street style summer fashionAnother outfit featuring a longer dressy shorts option. This whole outfit is perfect! Via Damsel in Dior.


dressy shorts pink white blouse black heels chic summer fashionCould there be a cuter summer evening outfit than this?! Via


Shop Dressy Shorts 

Happy Friday!

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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!