Header Logo
Close this search box.

Stylish Shorts for Summer

stylish shorts for summer
Cinq à Sept $325

The stylish shorts in this post are not the basic shorts I just featured in my flattering shorts post. You will not be sporting these stylish shorts every day, and most of these shorts won’t work on a ton of body types. They’re less about slimming and versatility, and more about creating a “look.” These shorts are here to make a statement.

We have printed shorts, leather shorts, pleated shorts, silk shorts, paperbag waist shorts, and all sorts of funky pieces that my fashion-forward fashionistas will be snatching up. Basically, any stylish shorts I come across that aren’t versatile enough to make it on my flattering shorts list — but are totally amazing — will be dropped on this list. But let’s start with my four favorite types of stylish summer shorts…

Tailored Shorts

stylish summer tailored shorts
J. Crew $98

When I think of dressy or tailored shorts for women, I think along the lines of Audrey Hepburn and Joan Collins in the 50s wearing their tailored shorts with little heels and a blouse. Whenever a client is interested in dressy shorts, these are my go-to brands that always provide:

  1. Alice + Olivia
  2. Cinq à Sept
  3. J.Crew

How To Wear Tailored Shorts: Pair silky tailored shorts with a silky top or blouse. If the tailored short is cotton or linen, pair them with a blousy top in a similar weight and texture.

Best Body Types: Dressy tailored shorts rarely have stretch which means they’re most flattering on rectangle body types or those who have medium-sized hips in proportion to their body.

Leather Shorts

stylish leather shorts
7 For All Mankind $168 $117.60

Leather shorts are year-round fun. Yes, you can wear them in summer in temperate cities — hello, San Diego. Those who live in sweltering heat may prefer to skip leather, whether real or faux, if your thighs are dripping with sweat. The 7 for All Mankind stylish leather shorts featured above are available at Bloomingdale’s, 7 for All Mankind, Zappos, Revolve, and Neiman Marcus.

How To Wear Leather Shorts: Pair them with silk blouses, tucked in tees, crop tops, and bodysuits if the leather shorts are high-waisted.

Best Body Types: Most body types can wear leather shorts.

Paperbag Waist Shorts

stylish paperbag waist shorts
Commando $168

Paperbag waist shorts are a go-to statement short. A paperbag waist is when the waistband has pleats that cinch at the “real” waist with a tie or belt. It creates a puffed or ruffled effect that resembles the top of a paper lunch bag when you wrap your hand around it. The Commando paperbag waist shorts pictured above are available at Neiman Marcus, Revolve, Zappos, and Amazon.

How To Wear Paperbag Waist Shorts: The absolute best item to pair with a paperbag waist is a bodysuit.

Best Body Types: Paperbag waist shorts work best for the rectangle body type, long-waisted women, or those with flat stomachs.

High-Waisted Printed Shorts

stylish high waisted shorts
Farm Rio $135

Printed shorts are not necessarily au courant. You must pick a bold short that really speaks to your personal style, and you must select the perfect color-matched top to go with them. For instance, with the shorts above, don’t you dare put a white tank with them. You must find a solid green or red bodysuit that matches the color in the shorts perfectly. The Farm Rio high waisted printed shorts pictured above are available at Bloomingdale’s, Nordstrom, and Farm Rio.

How To Wear High Waisted Printed Shorts: As I stated above, you must pair them with a bodysuit that matches a color in the print perfectly.

Best Body types: Those comfortable with all eyes on their bum and hips.

Best Stylish Shorts This Summer

stylish summer shorts
Generation Love $198

We shall update our post on stylish shorts every summer and continue to add new fashion-forward shorts regularly as I come across them for my clients. I drop all new additions below for your browsing pleasure. Feel free to mention in the comments if you have tried any of my recommendations and what body type you have. Our community of readers would love to know how it worked for your specific body shape, height, and needs.

Alice and Olivia Mara Waistband Shorts

stylish summer shorts
Alice and Olivia $265 185.50

Size Range: 0-14

Fabric: Shell: 100% recycled polyester; lining 1 & 2: 100% polyester

These shorts are available at Bloomingdale’s, Nordstrom, Alice and Olivia, Neiman Marcus, and Saks Fifth Avenue.

Wit & Wisdom Paperbag Waist Linen Blend Shorts

stylish shorts
Wit & Wisdom $68

Size Range: 0-16

Fabric: 55% linen, 42% rayon, 3% spandex

Sweaty Betty Revive Tie Waist Knit Shorts

stylish shorts
Sweaty Betty $68

Size Range: S-XL

Fabric: 90% cotton, 10% polyester

These shorts are available at Nordstrom, Bloomingdale’s, Zappos and Neiman Marcus.

Farm Rio Blooming Garden Belted High Waist Cotton Shorts

stylish shorts
Farm Rio $135

Size Range: XS-XL

Fabric: 100% cotton

These shorts are available at Nordstrom, Bloomingdale’s, and Farm Rio.

Michael Stars Peggy Smocked Waist Gauze Shorts

stylish shorts
Michael Stars $108

Size Range: XS-L

Fabric: 100% cotton

These shorts are available at Nordstrom, Amazon, and Michael Stars.

Free People Off Shore Tie Waist Utility Shorts

stylish shorts
Free People $88 $52.80

Size Range: XS-XL

Fabric: 50% cotton, 34% viscose, 16% linen

These shorts are available at Nordstrom and Backcountry.

Aldi Belted High Waist Shorts

stylish shorts
Cinq à Sept $325

Size Range: 0-12

Fabric: 69% triacetate, 31% polyester

These shorts are available at Nordstrom, Amazon, Neiman Marcus, and Saks Fifth Avenue.

stylish shorts
Cinq à Sept $295

Size Range: 00-16

Fabric: 69% triacetate, 31% polyester; lining: 95% polyester, 5% spandex

These shorts are available at Bloomingdale’s, Bergdorf Goodman, Revolve, Neiman Marcus, and Nordstrom.

Nike Yoga Luxe Tight Shorts

stylish shorts
Nike $45-65

Size Range: XXS-XXL

Fabric:63% nylon, 37% spandex

These shorts are available at Nordstrom, Nike, and Revolve.

Endless Rose High Waist Tailored Shorts

stylish shorts
Endless Rose $70

Size Range: XS-L

Fabric: 97% polyester, 3% elastane

These shorts are available at Nordstrom and Verishop.

Stylish Shorts from Years Past


I originally wrote this post years ago and update it regularly due to its popularity. I’ve left these photos below for nostalgic purposes. Whenever I update older posts, I love to hold on to a collection of images as a bit of a time capsule so we can watch how our style evolves.


A one-stop for some chic shorts is J.Crew. I just bought these printed shorts pictured above for one of my clients. They’re comfortable with a slimming fit. J.Crew also has some great solid color shorts, but a sleek printed short is an essential.


These shorts by Catherine Malandrino ($275) are for women with wide shoulders and small hips, referred to as an upside-down triangle shape. The draped sides are beautiful, but will add weight to any other body type. Feel free to pair these with a slim fit tank top and a cropped sweater for an elegant look.

Banana Republic

Next, I want to show you these stylish railroad print, linen shorts from Banana Republic. Obviously a pair of shorts where you want to tuck in your shirt. Love the way they tied the self belt.

Leave a note for Vanessa.

2 Responses

  1. I agree those summer shorts are very stylish. the last one was my favorite, I’m planning to buy that one. thanks for sharing.

Leave a Reply

Your email address will not be published. Required fields are marked *


wardrobe stylist

Items selling out are my reader's biggest complaint. Sign up for my weekly updates so you get first dibs.

Are weekly emails too much? Sign up for the monthly round up and receive my personal five favorite recent purchases. In my professional opinion, you should sign up for both!

* indicates required
Please enter your e-mail address.
What updates do you want from me?

Sign up for my newsletter

* indicates required
Please enter your e-mail address.
What updates do you want from me?