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.
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:
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 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
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
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
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
Size Range: 0-14
Fabric: Shell: 100% recycled polyester; lining 1 & 2: 100% polyester
Wit & Wisdom Paperbag Waist Linen Blend Shorts
Size Range: 0-16
Fabric: 55% linen, 42% rayon, 3% spandex
Sweaty Betty Revive Tie Waist Knit Shorts
Size Range: S-XL
Fabric: 90% cotton, 10% polyester
Farm Rio Blooming Garden Belted High Waist Cotton Shorts
Size Range: XS-XL
Fabric: 100% cotton
Michael Stars Peggy Smocked Waist Gauze Shorts
Size Range: XS-L
Fabric: 100% cotton
Free People Off Shore Tie Waist Utility Shorts
Size Range: XS-XL
Fabric: 50% cotton, 34% viscose, 16% linen
Size Range: 0-12
Fabric: 69% triacetate, 31% polyester
Size Range: 00-16
Fabric: 69% triacetate, 31% polyester; lining: 95% polyester, 5% spandex
Nike Yoga Luxe Tight Shorts
Size Range: XXS-XXL
Fabric:63% nylon, 37% spandex
Endless Rose High Waist Tailored Shorts
Size Range: XS-L
Fabric: 97% polyester, 3% elastane
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.
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.