Fashion Over 40: Stylish Shorts for Moms

Summer’s coming, and like it or not, that means shorts weather! There was a time when the idea of stylish shorts was an oxymoron. Shorts used to be more functional than anything, but these days shorts have definitely secured a place in the fashion scene.

Fashion Over 40: Stylish Shorts for Moms

Bermuda Shorts // Rolled Hem Jean Shorts // 4-Inch Shorts
8-inch Cuffed Denim Shorts // 6-Inch Shorts // 5-Inch Shorts

Which begs the question . . . who should wear them and who shouldn’t, and what shorts are appropriate for a conservative housewife who is trying not to lose her sense of style along with her waistline?

As with most trend topics, I would say these answers depend on your lifestyle, location, comfort level, and body shape. Let’s break it down.

Dressy Shorts

A couple summers ago, I started noticing dressy shorts worn with heels and a cute top for a night out. I love the look. It’s fresh and fun. I wear this look for date nights and blogging events and conferences.

how to wear black dress shorts

I think dressy shorts can be age appropriate and stylish if they’re the right length and they fit well. If you don’t think you can pull it off with heels, feel free to wear a pair of dressy flat sandals or ballet flats. You will still get the same effect, and it’s always important to feel comfortable in what you’re wearing.

26 Days of Fall Outfits: Shorts with Ballet Flats and Jean Jacket

In the photos above, I’m wearing the 4-inch City Shorts from Ann Taylor. I have these in three colors, and I love them. They’re well made, and you can usually score them on a pretty good sale halfway through the summer.

Every woman has different proportions, and you have to figure out what works best for you. A 6-inch inseam will hit most ladies mid-thigh, and is probably the most universally flattering length. At Ann Taylor, the Metro Shorts have a 6-inch inseam, and right now LOFT has a ton of choices in that length as well.

loft shorts

Bermuda shorts are an option too, but I think you have to be careful or these can look frumpy. Some women can pull them off, it just depends on your style and overall body proportion. Go for a slimmer fit for the more flattering look. I think they look best with heels.

bermudas with heels

Not everyone will feel comfortable in dressy shorts, and that’s okay. I do think at some level you have to like your legs. It’s a fun option, and if you want to try it, I say go for it. Just make sure you pay attention to fit and proportion.

Casual Shorts

I pretty much live in jean shorts in the summertime. I have a pair of cuffed knee-length shorts that I love, and I probably wear them way too much.

Casual Summer Outfit: Coral Striped Tank + Denim Bermuda Shorts

I also have cut-offs that are probably a little ridiculous for a woman my age, but I bought them when I was training for my half marathon, and I was feeling pretty svelte. Haha!


They were pretty snug last summer, so I replaced them recently when these cuffed denim shorts were on sale. I’m looking at them now and realizing they have a 3-inch inseam. Yikes! Well, I’ll have to keep working out, won’t I!?!

Cotton shorts are great for casual wear as well. I think I picked up these pink cuffed shorts at Old Navy last summer. They’re more of a relaxed boyfriend style, which isn’t my favorite silhouette. I think I need to update my closet with a couple pairs of those slimmer 6-inch shorts at LOFT.

Fashion Over 40: Shorts for Moms

Shorts: Getting the Right Fit

As always, fit is important. You don’t want your shorts too baggy, but you don’t want your shorts so tight that they ride up in unfortunate places, ahem. (Make sure to check out your rear view, ladies!!) I actually had to ditch a couple pairs of shorts because the rear view was not a pretty sight.

Again, the proper length will depends on each woman’s proportions as well as the height of heel you’re wearing. There is a range you can work within.

The Right Top

The other thing to consider when wearing shorts is your top. You don’t want it too long, as that will create irregular proportions. I also find that I’m more comfortable in tops that aren’t as tight as I might wear with jeans or longer shorts. The front tuck is your friend!

Shorts for Moms


Do you wear shorts? What are your best tips??

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