4 Classy Ways to Look Cute in Shorts

If you want to wear shorts this summer, go right ahead. Shorts can look cute and classy especially if you keep your look classic. What do I mean? Here are a few examples:



orange top with shorts

Tailored Shorts

Crisply tailored shorts are a good starting point for a summer outfit that is fresh and chic. Pair them with a bright solid top in a silky material – so much more classy than a cotton tee.

Add some fun by showing off your personality with an interesting bag. You can’t go wrong with metallic flats which work with anything and add a tinge of elegance. A great necklace, some bracelets..these all make a huge difference is you want to dress up your shorts look. Go for something bold, not wimpy and watch the compliments come rolling in.

Shop this outfit:




polka dot shorts

Black and white combined always looks chic. If you want to wear a print, then stick to a classic pattern like polka dots or stripes. This outfit above has a crisp graphic look that is even more fabulous when you pair with a bright purse. Instant energy!

A little height in the way of a straw or rope wedge sandal gives your outfit a summery feel and elevates your look, quite literally!

Shop this look:


SUMMER BLUESShorts - White Bermuda

A crisp pair of white shorts teamed up with a chambray shirt, and metallic flats add a touch of causal chic to your summer wardrobe. Don’t you love this ethnic inspired bag that looks like you’ve been touring Morocco!

Shop this look:


Boho - Shorts

Are you more of a free spirit who enjoys a boho look? Then here’s a shorts outfit with a slight hippie vibe. Pair a cute tunic with a pair of khaki shorts, a fringe bag and some flat sandals and you have a relaxed ans slightly funky summer look.

Shop this outfit:

For more ideas on how to wear shorts, check how I wore them!

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  1. I’m 43. Others say I look like 29, cuz I am 5’2 feet, 29 inch waistline, I can wear shorts,skirts and mini dress which are comfortable for me!!!! and I look too pretty so others say!!!

  2. I could totally see many cute people wearing the boho outfit even under 40.

  3. I say opt for a skirt instead of shorts! They are so cute- and much cooler (meaning a little more breezy). You can pair a cotton skirt with flip flops and a tank and look stylish! Now that it’s fall- this conversation may be a little late… but had to add my 2 cents!

  4. Go Kim! Wish my husband liked it when I wear sexy…..think he’s more jealous than anything but he sulks the minute I try to look sexy! You wear your shorts and keep looking good,feel good when your man tells you this! Enjoy! I envy you! I look good but hey,this man of mine likes to peep at the other woman,some even far more dam ugly than me but hey, we can sit in a public place and he will make me feel like i’m the ugliest woman alive though I know i get looks from other men, some even younger than me! You go girl!

  5. Hi, i turn 50 this year. I am still in good shape though i never like wearing short skirt or shorts. I need a change, i like to wear fashion items and looks younger than my age, i also like to try out different or new ideas. This winter i bought myself some leggings which i wear only with a long top, jacket or jersey with boots. I must admit,it looks good and i feel good. The other day “something came over me” and i bought myself a short short in denim and also a very short skirt which i tried on with my leggings and boots, it looks really good though i will never go outside because i feel it’s not appropriate for older women. I really want to wear this style though with a long jacket, cover up of course when going outside. You may ask “why do i bother then”? Well, this is to feel good for myself,i don’t want to show my nice legs and sexy clothes out there, i want to know inside, and feel, that i look sexy for me. Am i weird? Hope not but if i do,are there any women out there that does these kind of things? I always try something new,not always proper for my age but hey, what the heck, if i feel good then stuff the rest right? I cover up anyways when outside the home,what does it matter what i look like underneath a pretty coat? I’ve always been a dark head gal,started turning grey the same age most ladies does, i hated it, then started to dye red,black,brown and any other colour one can think of. Recently i started to like the grey fashionable look, decided to go through the whole proccess in turning from red to blond, then to grey eventually. Still reshearching on this but it will come sooner than later. Why do we have to look like a granny if there’s still a lot of spark left in us? I get looks from men and even from woman…..but not good one’s from woman but i also don’t care. My own husband is very old fashioned concerning their woman,just like his father,etc though i see the looks he gives other sexy woman but he turns quiet and sulky when i look good,young and sexy! I hate this and one of the reasons why i feel i need a change,for myself and not even to spite him but just for me and me alone! Careful, thinking of getting a tattoo in a very classy manner,somewhere neat, not tacky and cheap though stylish,small yet still there to make a statement. What do you other gals think of my ideas?

  6. Im just a little bit over 40.My legs are in pretty good shape so I do like to where shorts on the short side. My husband likes me to where high heeels with them so I make him happy.

  7. Nice tip about shorts – Unfortunately in Australia it’s hard to find shorts that are good for over 40 Ladies. Most styles sold are for the very young, unless you want the ‘granny version’ – elasticised waist in pastel colours! Yuk! Any Aussies who know a good place to find over 40’s shorts please let me know.

  8. Shorts at 40, just to or above the knee may be ok, but for me, at 56, that length just highlights what age has done to my knees. Either shorter (several inches above the knee) or covering the kneecap/just to the top of the calf is much better – which technically I guess are not shorts! (I have very long legs, so the longer length works). To wear the shorter look, I’m finding that a skort (with the ‘skirt’ part in front and back, not just the front) is more flattering & just as easy to wear as shorts – & easier to shop for.

  9. Hi Deb, Just had to say Hi and note that it was amazing how my first summer after turning 40, shorts are suddenly an issue! Thanks for your advice. Looks like I have some shopping to do.

    –Amy Tiemann

    • Hi Amy,
      LOL!!! Great to hear from you and to hear your finally old enough to be official! Glad you found my advice helpful. Ie want you to still have your mojo with your wardrobe!

  10. Hi Deborah,

    Just a quick note – I really en-JOY reading your tips over 40! I find them incredibly helpful, practical and inspiring! Keep them coming!!