21 Stylish Shorts Outfits for any Age

Going away on vacation and planning on taking some shorts? There are dozens of styles of shorts, and hundreds of ways to wear them, so what’s a good look for a gal our age? Here are 21 stylish shorts outfits to inspire you.

1. Bell Sleeved Beauty


A soft flowy tunic with billowy bell sleeves is a chic carefree look with tailored dark shorts.


2. Ruffles add Charm

Delicate ruffles at the neckline and sleeves of this flowery tie-neck top add a very feminine touch to a classic pair of shorts.


3. An Off the Shoulder Top Dresses Up Shorts


This romantic off the shoulder blouse is perfect for those times when you want to dress up your shorts and wear them off the beach. Add crisp white accessories for a knockout shorts outfit.


4.  Try A Pair of Cute Paperbag Shorts

shorts outfit over 40 | floral waist tie shorts, yellow sleeveless blouse, lilac bag | styled by Fabulous After 40

Add a sleek, sleeveless shirt to a pair of flowery shorts, and you have a pretty, ladylike look. Beaded tassel earrings are fun and modern to pair with casual shorts. The purple crossbody bag is sporty and ties the whole look together.


5.  Look Vibrant in Bright Bermuda Shorts

Shorts outfit over 40 | Pink Bermuda shorts, paisley print tunic top | styled by Fabulous After 40

Bermuda shorts are back, and the newest ones have built-in stretch, which gives them a super comfortable fit and sleek look. Wear them with a longer top and a cute pair of slides for a sophisticated summer look.


6.  Gingham Shorts Say Summer

shorts outfit for over 40 | black and white gingham shorts and white peasant blouse | styled by Fabulous After 40

Gingham is a natural choice for shorts. Pink or baby blue denim can look a little sappy over 40, but these black and white gingham shorts make up for that. They’re cute but not over the top.


7.  Sporty Cargo Shorts

shorts outfit over 40 - tan cargo shorts and turquoise t-shirt styled by Fabulous After 40

When you want to create an adventurous, active summer look, cargo shorts are a perfect choice. Top off a pair of khaki utility shorts like these with a simple cotton tee in a bright color to add some punch.


8.  Short Shorts Can Work

Shorts outfit for over 40, 50 | short red shorts, print sleevless blouse, white jean jacket and accessories | styled by Fabulous after 40

Short, colorful shorts are always in style, and if you have the legs for it! This cute outfit looks smart because it appears well thought out. Everything coordinates, the sandals are adorable, and we’ve added jewelry and a jacket to make it look a little more polished than just wearing it with flip-flops and a plain tee.


9.  A Wrap Top Shines with Bermuda Shorts

how to wear shorts over 40 | long white shorts, blue wrap top, tan acessories | styled by Fabulous After 40

Bermuda shorts can look classy and modern styled with a summery wrap top. Add a pair of cute wedge sandals and a relaxed tote, and you have a great vacation look.


10.  Pretty in Pink

Ways to wear shorts over 40 | blush pink shorts, floral elbow tie blouse, snakeskin flats, tote | styled by Fabulous After 40

Pink is a hot color this spring. These soft pink blush shorts are elegant and feminine and look lovely when you team them up with something equally as feminine such as a pretty floral blouse. A chic pair of snakeskin flats, gorgeous earrings, and a sleek tote take a basic pair of shorts to a whole new level.


11. Chambray Shirt Chic

how to style shorts over 40 | olive cargo shorts, chambray shirt, backpack bag, statement sneaker| styled by Fabulous After 40

Are you a sporty type who also likes to look chic? Then a pair of relaxed cargo and a soft chambray shirt is a winning combo. This kind of outfit looks great with a more casual bag, like this backpack style, and is perfect with a pair of comfy statement sneakers. This is what you might call a chic adventurer look!

12.  Peasant Style Pieces are Trending


Gauzy peasant style tops with lace and ethnic embroidery add boho charm to basic khaki shorts. Add a pair of lace-up sandals for a touch of summer glam. A chic bag pulls this cool shorts outfit together.


13.  Good Lookin’ Gingham

how to style shorts over 40, 50 | Gingham bermuda shorts, white sleeveless lace top, white sandals, raffia bag | styled by Fabulous After 40

Checks have been trendy in the last couple of years, especially for those who like more a classic look. This ladylike outfit is pretty and conservative, but still very modern. Gingham always looks great with natural materials like this raffia bag. Classic sandals and stud earrings with a modern twist finish the look.


14.   Paperbag Shorts + a Preppy Polo

Paperbag waist shorts that are high waisted and tie at your tummy are feminine and flirty. This is a cute teamed up with this floral polo, and summery wedges is fresh and modern.


15.  Red Hot

These firey shorts give new meaning to the term hot pants! Bright red look sporty and fresh worn with a classic white shirt with a twist- cutouts at the shoulder.


16. Artsy Vibe

A geometric print in an unusual mix of bold colors is like a piece of art when worn with inky black Bermuda shorts.


17.  Soft Off the Shoulder


Slouchy, relaxed, and super comfy. This off the shoulder tee with the fancy trim looks right at home with your favorite denim shorts.


18.  High Waist Shorts



These cute perforated shorts with the ultra-high waist take has a sweet retro vibe that’s almost pin-up girl. How fun when worn with a darling blue chambray blouse with sweetest elbow tie sleeves.


19.  Breezy Scarf Tie Look

Here’s a perfect beachy look that’s light and breezy! Wouldn’t this be perfect for a day of sand, surf, and sailing?


20.  Scalloped Edge Shorts

Pretty details like scalloped edge shorts lend a feminine feel to these sleek mid-length shorts. A cute blouse and colorful, classy bag give this shorts outfit a chic look.


21. Gold Standard

A great pair of gold sandals is all you need to uplevel shorts to a dressier look. Go for the gold!


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

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One thought on “21 Stylish Shorts Outfits for any Age

  1. My legs are still my best feature even though I’m a few months shy of 70. I would never give up shorts. However, one can’t stop the inevitable crinkling that happens to the inner thighs. I have simply lengthened the shorts. A Bermuda length is my very best friend and I have an entire collection of colors.

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