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!

Don’t miss a post!

Subscribe to get email updates! In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox. Don’t miss it!

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

Join The Conversation

27 Responses

  1. I absolutely love Ann Taylor’s shorts—I had a pair in white for the longest time until I lost weight!! But this is such a modern and chic shorts outfit!!
    I’ve been embracing shorts even though I’m old…in fact, I wear them more in the last couple of years, then I did 10 years ago!!

  2. Cute look I am finding myself wearing a lot of shorts this summer usually I wear summer dresses, guess when I broke my arm I made a change on my clothes, its been 6 weeks my arm is out of cast, but still can’t move it certain ways my favorite work now is owe.

      1. The 7th of July I will start working with someone to help build the strength back up in my arm, will have to start out slow and work my way up. Thank you for the reply I Love your post

  3. I hope you will keep shopping your closet, like we do, when choosing a handbag and shoes to complete an outfit.  This is a very nice dressier casual outfit.  I bet y’all are so excited to get moved and begin this next chapter in your family’s life.  I would be bursting at the seams with excitement!  I pray that all of the events this week go very smoothly for y’all!

  4. You have the BEST posts! Love this outfit on you and the information on wearing this. I always have such a difficult time putting outfits together that look good and your blog is very, very helpful!! Thanks!!

  5. You have the greatest ways to style and wear shorts. I will admit the shorts have been a thing of the past for me for awhile until last summer when I started to wear them around the house again, as I liked them on me again… after dropping a few pounds. Now I need to venture out in baby steps in public. LOL

    1. Try it! I actually stopped wearing shorts for a while too, but I think they’re possibly more “popular” now? I mean, I know shorts have always been a summer staple, but I feel like they’ve gotten more stylish over the past few years.

  6. Regarding your TV interest. There’s a new series on HGTV, Boise Boys. It has become one of our favorites. Never have got on board with Good Bones. Love Home Town. Ben and Erin are featured in the July HGTV Magazine. Enjoy Flip or Flop Las Vegas, Flip or Flop Atlanta, Desert Flippers and Restored By The Fords. Can’t wait for a tour of your new digs!

  7. Hi JoLynne, good post, as usual!    I was wondering about the rise of these shorts.  It seems the length of shorts get all the press, but these look as if they may be fairly short rise.  I wish all pants/shorts would be advertised with the rise in inches instead for the store’s opinion of low, mid or high.     Thanks for any more information you can give on these.  🙂

    1. Yes, I don’t know why they don’t give measurements. I would say these are mid-rise, probably a 9″ rise? But they may have changed them since I bought mine. That is the kind of thing I’ve noticed designers will alter year to year, and they don’t always rename the pieces. I think the newer City Shorts have wider legs too. 🙁

  8. What an interesting background for your pictures! I like this casual outfit because it tells me that it is okay to go with a simple look and not think about it….does that make sense? I am good with you using the same accessories, shoes, and handbags with your outfits as it shows just how versatile pieces can be. On that note, was there a reason that you didn’t wear a necklace with this outfit? I always think that I *have* to have a necklace with almost every outfit. Thanks for all that you do, Jo-Lynne.

    1. Hey Bev. So yeah, I tend to be more of a minimalist with jewelry, and if a top has a pattern or an interesting neckline, I usually opt for bolder earrings and forego a necklace, although in this case, while the top is striped, the neckline is fairly simple and probably could have used a necklace. That said, the neckline is a nice moderate scoop that isn’t deep enough to need a filler or high enough that I felt I needed a long necklace or a statement piece to create a different shape or draw the eye elsewhere, so I don’t think I thought much about a necklace.

      The day we shot this look, I had 5 or 6 outfits with me, and sometimes I just don’t plan very well when I have to put that many outfits together at once. Jewelry is usually the last thing I think about when putting an outfit together, and when I get dressed here at home, where I have my entire jewelry arsenal at my fingertips, I play around and find just the right thing for my outfit. But when I pack up 5 or 6 outfits to take to a photo shoot, I’m lucky if I end up with shoes and a bag to go with each one, lol! Often I just grab a few of my classic jewelry pieces and throw them in my bag as I head out the door, so when I change in the car and swap out my jewelry, I don’t always have my first choice of accessories. In the case of this outfit, I don’t think I thought much about my jewelry when I was packing the car.

      And that is probably WAY more than you wanted to know. HAHA!

      1. Thank you for your response/explanation as it really gives me the kind of information that I need when critiquing my own outfits.

  9. I LOVE this outfit!!! Stripes and leopard together are great, one of my favorite things to pair together. I was actually wondering over the weekend of ballet flats were okay to wear with shorts. Glad to know they are! 

    Would you wear ballet flats with denim shorts or stick to dressier type shorts? 

    In regards to your email questions, I have found that despite doing a summer fashion challenge, I tend to stick to basics like plain tees and shorts. I like the outfits you have featured and would like to see more remixing pieces from your closet versus new stuff. I believe I  aam done shopping for  clothes

Leave a Reply

Your email address will not be published. Required fields are marked *

Close this search box.