How to Wear Shorts with Ballet Flats

Typically I think of shorts as a casual wardrobe piece for wearing with flat sandals or fashion sneakers, or I will dress them up with wedge sandals for a daytime event, but it’s also fun to pair your shorts with ballet flats.

How to Wear Shorts with Ballet Flats for Women Over 40: dressier than jean shorts and a t-shirt, but still cool and comfortable for those hot summer days!

When pairing shorts with ballet flats, I usually start with a chino style short. I don’t want anything too casual (i.e. denim shorts) because the ballet flats have a slightly dressier vibe than most of my flat sandals and sneakers.

These shorts are the Ann Taylor City Shorts, and I’ve been wearing these for YEARS. In fact, this exact pair is a few years old. They’re such a classic style that they bring them back year after year, and I now have them in white, black, and navy. The material is good quality, heavier than my Old Navy Pixie Shorts (for comparison), and they have a really nice fit.

I love the flattering scoop neckline and the rivets on the sleeves on this stripe top. Little details like that make all the difference!

My shorts have a 4 1/2” inseam so they’re not super short, but they are a little shorter than mid-thigh on most of us. (I’m 5’5″ for reference, and I’m wearing the size 8.)

If you prefer slightly longer shorts, Ann Taylor Mid Shorts have a 6″ inseam, and Talbots Girlfriend Chino Shorts have a 7″ inseam. I’d be very careful about wearing Walking Shorts or Bermuda Shorts with a 10 — 11″ inseam. They really only look good on those who are tall, thin, and long-limbed. I know, that’s a tall order! Haha… see what I did there?

STYLE TIP >> A mid-length short is universally flattering and easier to wear than Bermuda shorts or short shorts, but you will want to experiment to find the exact inseam length that looks best on your unique body. See my Dos and Don’ts for Shorts for more.

If you absolutely do not wear shorts outside the house, black cropped pants or a casual black knee-length skirt would totally work with this outfit. Choose a style that works best for your body type. Cropped flares would be fun and modern with this, or a black jean skirt would also work.

I love the flattering scoop neckline and the rivets on the sleeves on this stripe top. Little details like that make all the difference!

This top is from White House Black Market, and it’s a nice quality jersey material that isn’t see-through and holds it shape without being clingy. I’m wearing a small, for reference. I love the modest scoop neckline and the rivets on the sleeves. Little details like that make all the difference!

I decided to go for a little pattern maxing and wear leopard flats with this outfit. Black and white stripes pair really well with leopard print — it’s an easy outfit formula I rely on again and again. If mixing patterns makes you nervous, this is pretty much a fail-proof combination.

How to Wear Shorts with Ballet Flats for Women Over 40: dressier than jean shorts and a t-shirt, but still cool and comfortable for those hot summer days!

I like how these leopard flats are a patent leather as opposed to the more typical hair calf version. I have a pair of the hair calf ones too, and I like them as well, but these are fun for a change.

Unfortunately they’re being discontinued and sizes are limited, but if you luck out and find your size, they’re on sale at several retailers. You can also check Zappo’s, Shopbop, and Neimans for more sizes.

Tory Burch Minnie Travel Ballet Flats in Leopard

I carried a cognac leather bag to work in with the colors in the shoes, and also I like how the neutral bag tones down the crips black-and-white outfit and warms it up a bit. A black bag would totally work, but it would look more predictable.

This is an outfit I’d wear in the summertime to the mall or to meet a friend for coffee or a casual lunch. It’s a little dressier than jean shorts and a t-shirt, but it’s still cool and comfortable for those hot summer days.

How to Wear Shorts with Ballet Flats for Women Over 40: dressier than jean shorts and a t-shirt, but still cool and comfortable for those hot summer days!

striped top // black shorts (longer option/budget option) // leopard flats (option) // similar bag (option)

photo credit: Alison Cornell

Be sure to visit Cyndi and see the summer outfit she’s styling today!

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