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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35 Responses

  1. Shorts have always been my go-to outfit in the summer months., that and long maxi skirts. Talk about different lengths! Haha But since starting my blog last September, I am dreading the day when I am going to be styling shorts. Funny how I don’t care to subject people I run ito in person with my looks, but I am hesitant to share to people on the internet.

    1. I’m going to check out your blog for a shorts styling! I’m 54 and the legs are showing some wear and tear. I’ll be curious to see your recommendations.

  2. Great information about shorts. For me, the days of shorts are over, I wear skimmers/ capri’s instead so you gave me some good ideas on color combos. Very chic looking Miss Jo-Lynne Shane!

  3. Love your denim cuffed shorts. Very cute. Do you use a self tanner? If so could you please tell us what kind?

  4. Very stylish look for summer! You look great in all the shorts styles! Since you mention that the front tuck is our friend, I have a question. Do I need to wear a belt if I front tuck on shorts with loops? I am short waisted and a belt seems to visually “divide my middle” and make me look thicker. Any thoughts?

    1. It’s totally optional. I see stylish women going with and without a belt. I prefer the finished look of a belt personally, but I also carry my extra weight in my middle, so I know what you mean.

  5. I really like all of these looks. Although at my 5’5″ stature, the longer Bermuda ones probably are not for me. I have a couple of pair, and I usually feel somewhat frumpy in them. Thanks for styling the dressy shorts! I have a couple very nice pair I bought at end of seaon last year and just haven’t figure out what to do with them. I love the upgraded look, but just need a top that look right.

  6. Hi Jo-Lynne,
    I love the way you look in your shorts, you’ve got the legs for it! I have only ever worn shorts as a work out/hiking/slumming around in the garden thing, so I’m feeling very unsure about shorts as an ‘outfit’. I am not crazy about my knees – although I have slim legs, I have always felt my knees are a bit stubby. I think if I had a good tan going, it could work though, so I will have to try your self-tanning tips and see how I go. Here in the UK, not many women over 25 wear shorts with bare legs. Maybe it’s the fact that it never gets that warm in summer…

    1. Interesting, and that makes sense. Here it does get quite hot so at some point, you have to break out the shorts or a skirt or something. Tanning definitely helps me feel more confident in the shorter shorts.

  7. I really like how you give options Jo-Lynne!!
    While I was working, I’d never wear shorts (for some silly reason I didn’t think it was professional—gosh, I’m glad that’s done)
    But especially when it’s really warm, I think shorts add nice variety to our outfits! (Although I will state the case for skirts—usually they cover the back of your legs when you sit down in the hot car–ha ha)
    I know many women my age tend to pooh pooh shorts saying their legs aren’t perfect—my answer is always—my whole body isn’t perfect (there’s this huge scar right on the front of my face and you don’t see me covering it up with pants).
    I think once we get past the fact that perfection is not obtainable, it makes fashion way more fun!!
    I love the color of your pink shorts, but they do look somewhat baggy (although some of mine get that way at the end of the day).

    1. LOL, you crack me up. I definitely agree we have to accept imperfection, but there are also some great alternatives to shorts for women who would prefer not to wear them. That post is coming up on Thursday! 🙂

  8. cute outfits! I’m 5’1″ so I wear my shorts around the 4″ inseam. I found some 50% off at Belk. Crown and Ivy is the brand. Love them, especially the linen ones!

  9. This is timely, as I just recently bought a few pair of shorts, with great hesitation. I hate my legs. They are fat, it’s where I carry all of my weight. Cellulite city. I prefer not to show anything above my knee. But we have a family vacation coming up, and I knew I’d be miserable in pants, so I sucked it up. I got the 7 inch twill shorts and 9 inch bermudas from Old Navy. Both are long enough to cover most of my problem areas, and they’re slimmer through the leg so not too frumpy (I hope). I will never be a fan of shorts but these get the job done. I have to say I’m envious of all of you ladies with slim legs! I’ve had this struggle since high school.

  10. Thank-you so much for this post, JoLynne. I think you’ve hit a great topic. So many of us are self-conscious about wearing shorts, especially as we age. I think this kind of dialogue is important in that it encourages us to consider our feelings on body image. And warm weather outfits seem to often be left out of fashion posts and discussions. Living in southern Delaware, it gets HOT in the summer. I need shorts, so thanks for sharing.

  11. I guess I’m a little ignorant about shorts, but are the 4, 6, and 8 inch measurements the stride..crotch seam to hem?

  12. I am 5’3″ …so I try not to wear the shorts with cuffs it makes my legs look shorter. I thought my legs looked awful until I started using self Tanner or spray tan. It really helps cover up like a pair of hose. But I have always thought if you don’t care for your toes wear a closed sandle and if you don’t care for your legs wear skirts or Capri’s there are so many options lol

  13. LOVE LOVE LOVE that purple top on you, super flattering color!!! Thanks for all the posts and advice :).

  14. Some really nice options! I’m way past the short shorts age. And there’s some new “print” actually starting to decorate my legs…but I’m all about shorts, skirts and dresses for summer!

    YOU look great in all of them…

    I’m the same age as Sharon, though, so it’ll be the longer ones for this old chick! 🙂

  15. As i venture in my 40s i find this to be daunting. I have always lived in 4 inch inseam shorts, but now they feel too short. I find myself reaching for the bermuda shorts, but they are not the right length for me. My summertime struggle!!!

  16. I love you long denim shorts and striped tank top outfit. Where did you get those pieces if you don’t mind sharing.. I think you look amazing in your cut off shorts, tee shirt and flip flops.. Love your blog.. I will be 44 this fall and I am a mother of 4.. 2 teenagers 18 and 17 and 2 littles 3.5 and almost 2.. Your style fits me perfectly. So happy I found you..

  17. I’ve finally kicked the bermudas to the curb! I am 46, 5’6″ and a size 10…they just weren’t flattering on me. Definitely made my legs look shorter. I purchased several pair of the 6″ Riviera shorts from Loft and I LOVE them! Huge difference! My 21 and 19 year old daughters have been trying to convince me to wear my heeled sandals with the shorts, but I wasn’t too sure about that. After reading this post and seeing how great it looks on you I may have to try it…date night sounds like a perfect opportunity to do so! Thanks for the post! 🙂

  18. I think you look great in the cut offs. I am almost 56 and live all summer in shorts. Mostly I wear cuffed or rolled up denim in blue or white – and hope I never have to give up wearing shorts!

  19. Great post. I also think you look fantastic in the short cut offs and vneck tee-wear that more often! I’m still a lover of short shorts at 36…can’t help it. My mom is, too!! But maxi dresses and lightweight summer dresses rock also. Once in a while I wear some bermuda shorts I have with flip flops-I don’t like how they look with anything else…but flip flops make them ok-I think because it’s showing more skin and not breaking up that leg/foot line.

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