Shorts for Moms

I’ve been known to say on more than one occasion that my time for wearing shorts has come and gone and that ship had long sailed. I was pretty content living in Bermuda shorts and capris in the summer months and figured my thighs would probably never again see the light of day, and I was okay with that. It was an age and comfort issue as well as a style choice.


Banana Republic Bermuda Shorts // Ann Taylor City Shorts // Gap Slim Denim Shorts // Paige Cuffed Denim Bermuda Shorts // Gap Stripe Summer Shorts // Gloria Vanderbilt Cate Twill Shorts

For a while there, capri pants and Bermuda shorts were stylish, and mid-length and shorter shorts, well, weren’t. I mean, shorts always have their place, I suppose, but suddenly they are very much on trend. Now you see shorts for almost every occasion. In fact, they are even fashion-forward when worn with a suit jacket.

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

First, let’s talk about the dressy shorts trend. A couple summers ago, I started noticing dressy shorts worn with heels and a cute top for a night out. For some reason, I loved the look. It just was fresh and new and fun, and I finally got bold enough to try it.

I bought a pair of white dress shorts at Ann Taylor before a blogging conference and wore them for the first time with wedge sandals and a cute black top with ruffle detail to daytime conference events. At first I felt awkward, but I loved the look so much that I soon got used to it and found myself using any opportunity to wear the outfit. Before I knew it, I was wearing the look for date nights and even business dinners.

dressy shorts for moms

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. You will still get the same effect, and it’s always important to feel comfortable in what you’re wearing.

For the record, in the photos above, I don’t feel that the coral shorts are nearly as flattering as the white ones. They weren’t as good quality, for one thing. The thinner fabric wrinkles easier and doesn’t hold its shape as well as the thicker fabric of the whites ones. Every woman has different proportions, but for me, I feel best in shorts that are what I’d call a mid-length. They hit about halfway up the thigh. If they were any longer, they would look dowdy, but if they were shorter, I’d feel like a hoochie mama (ha!) You can get away with shorter shorts if you’re wearing flat shoes, and/or if your legs are on the shorter side.

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.

Casual Shorts

The first pair of shorts I bought that weren’t knee-length were a pair of khaki cuffed shorts at Banana Republic. I believe I got them about three years ago. I remember that it felt like a big decision. Was I really willing to go back to shorts? Nearing 40, a woman starts to think about these things. Can I still get away with them? These were pretty modest and a good place to start. Not too short, not too tight, they were easy to wear and very comfortable. I wore them for a couple of seasons before adding anymore shorts to my wardrobe. 

Then last summer I got really brave and bought a pair of denim cut-offs. I’ll admit, I felt pretty silly wearing them at first. I almost didn’t buy them, but once I tried them on just for kicks, I loved them so much, I decided to give them a try. They seemed perfect for lazy summer days at home. I ended up wearing them about three times a week all summer long.

After that I added a few more shorts to my wardrobe. I didn’t want to spend a lot so I bought most at Old Navy. I ended up wearing them a ton. Shorts and tops are now pretty much my casual summertime uniform.

Shorts: Getting the Right Fit

Again, fit is important. You don’t want your shorts too baggy. I don’t really like the ones on the far right for that reason. They are actually a size larger than the other shorts, because I was trying to find the right fit for the waistline.

Then again, you definitely 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.

If you’re a mom and carry a bit of extra volume in the middle as many of us do after carrying babies, you may have to work a bit harder to find the right fit. It takes some trial and error, like most things.

Again, the proper length will depends on each woman’s proportions as well as the height of heel you’re wearing. There is some range you can work with. I clearly have some that are shorter than others. I actually think the shorter ones are more flattering, but I’m more careful where I wear them, and those I only wear with flats.

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.

You may find that it works better to tuck your top into your shorts. This was new to me, as I haven’t been a tucker for years, but as usual in the world of fashion, what goes around comes around, and tucking shirts in — either all around or just in the front — is on trend again.

Shorts for Moms

If you’re in the market for shorts this summer, here are some you may want to try. Banana Republic has a large selection of shorts, and they are a very nice length — not too short but not too long. Ann Taylor has a few shorts styles right now, and from my experience, they are very good quality, especially if you want a pair of dressier shorts. Check Gap for more casual shorts styles. They have some boyfriend roll-up shorts, printed shorts and lots of choices for denim shorts — both short and long, and every shade of wash under the sun. Target has a lot of cute styles too!

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


  1. says

    My legs are my favorite boy part. That being said, they still need a short of a decent length. I like a mid thigh length. Anything longer I look stubby, anything shorter I look like a lady of the night. Neither of those are a look I am going for!

  2. Susan says

    I live in Texas. It’s just impossible to not wear shorts. White House/Black Market makes a great line of twill/khaki cargo type shorts that wear really well. I like the boyfriend denim style by Kut From the Kloth (Nordstroms). I am 5″10 and have always felt shorts were flattering on me as long as they weren’t too short. My problem is finding nice, well made tops/t-shirts that are long enough without being too tight and clingy…but not too baggy!

    When I’m home and free after a long day, honestly, it’s just Nike shorts and a t-shirt!

  3. says

    Oh this subject just makes me cringe!! I’m 50 and there are veins on the side of one of my legs that make me feel self conscious. This might be the year to zap them! We live in Texas where it’s just too hot to say I’m not going to wear shorts. Cute shorts that fit well are just as important as the right jeans.

  4. says

    I have such a difficult time with shorts — I mostly wear dresses or skirts all summer. I don’t know what it is, I still see them as very informal and found myself changing out of them when going to dinner or meeting up with a friend. Maybe its all of those wears of my mother saying the didn’t like them?? I don’t know, but you look great. Oh and I don’t like how my thighs look — yeah, that too. But I like the cute styles and designs and I realize shorts have come a long way. I would wear the longer fitted ones Jennifer Aniston style…those I can handle!

  5. says

    What an awesome post! I struggle with wearing shorts more than any other item. There are so many that are too short or too long and so few that are just right. Thanks for these recommendations, this will come in really handy in the coming weeks.

  6. Deb Peters says

    Check out Talbots, they have short in lenghts 7,9,11and 13 inch. Im 58 year old and dont feel I should be in the 7 or 9 inch lenght but I sure do look ok in the 11 inch. They cost $49.50 but have regular sales if you keep your eye out. Deb

    • Joyce Tutone says

      Deb, I’m 10 years older than you but I live in Charlotte NC and I could not survive the summer without shorts. I have several from Talbots as well. I’m 5’3″ so I wear the 10 or 11 inch as well. Loft also sells 10 inch so I buy some there. I’ll wear them at home or for daily errands but switch to a casual dress for dinners out or lunch with friends.

  7. Shannon H says

    I’m in Phoenix so I wear shorts almost 9 months of the year (yep, it’s already shorts weather here). I’d say my style has evolved from super casual (denim shorts and casual tees) to nicer “docker” type shorts and I’m trying to gather a good collection of nicer tops as well. It’s easy to get bored with such long summers!

    One thing I always look for is a long shorts. I’m self conscious about my legs (cellulite abounds) especially when I sit and the shorts creep up. But last year I found some super cute navy shorts with white anchors on them–a 6″ seam length. I like them and would be wiling to add another pair of similar length this year. :-)

  8. Beth says

    I can’t wear shorts to work, so I never have many of them, but I absolutely need a new pair or two. The last pair I bought I found for just a couple of dollars on clearance, and they were slightly too big when I bought them. They’re probably 3 sizes too big now, and shorter than I remember them being. The only other pair I have were given to me and I don’t like the waistband. Sigh. Maybe I’ll like some of the ones at Target, I have a gift card for there.

  9. Mary B says

    This is a great post! Thank you for talking about shorts….I love your variety of colours and prints!
    I live in Florida and find that shorts/skirts are the ONLY comfortable option during the summer. I prefer dressier shorts and find that Talbots shorts fit me well. My legs are not thin so I prefer the inseam to be between 7″ to 11″. Like you, I’ve started to wear platform sandals and higher shoes with shorts for a casual night out. My latest venture is finding tops that are a bit dressier than just a pain tee. If the shorts are solid then I feel compelled to have some sort of pattern or print on the top. Normal or not?

    • says

      I don’t know that I’d need a print on top – I’m kind of a plain jane. But I do agree that I like to have something dressier than a plain tee. Although if the shorts are a bold color, sometimes a white tee is all you need as long as you have some statement jewelry. :-)

  10. Nicole says

    i just bought a pair of Pixie shorts at Old Navy. I already had crops in the same material. It’s got some stretch, but holds shape and doesnt wrinkle! Express has cute dressy shorts, I shop at an outlet. I love my legs, so I’ll wear shorts forever.

  11. Kathy Cochran says

    Thank you for this post!! I live in Phoenix, so shorts are pretty much worn most of the year. I too have struggled to find the right fit and not have them be too short. I love the outfits you showed, great inspiration.

  12. kim says

    I love shorts but have a very hard time finding ones that really fit me well. I have 2 pair I love. The others I wear but really don’t feel good in them.

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