This post is updated regularly. Last Update: June 2021

most flattering womens shorts
t-shirt: Madewell, shorts: Madewell (another wash HERE), flats: Rothy’s, earrings: Dear Survivor, sunglasses: Blenders Eyewear

Women’s shorts can be the bane of existence for some, and a uniform for others. My clients who run really hot can’t get out of them, but most of my clients fear shorts. “No shorts!” a client wrote me in a recent email discussing her summer capsule collection. “I hate my thighs” another client explained to me. “Are shorts too young?” another client asked. Here’s the thing: it’s hot and women’s shorts are an energizing look — especially this summer. The selection is the best I have ever seen on the casual front. So let me put your fears at ease with a delicious selection of totally flattering and absolutely comfortable shorts. My clients are LOVING them!

Tops To Go With Shorts

Part of the fear of shorts is looking dumpy. First of all, none of the shorts listed below are unflattering. But you do need to pair them with the right tops to look as fresh and flattering as you possibly can. The best tops to go with shorts are, well, short — shorter tops, shirts that tie at the waist, and bodysuits or leotards if you wear high-waisted shorts. If you want to wear a longer top with shorts, just tuck it in, either fully or via the french tuck (tuck in only the front of the shirt).

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Shoes To Go With Shorts

My favorite shoes to wear with shorts are sandals, flip flops, a casual flat, and sneakers. You can also rock an open-toe casual bootie, and you can always dress up shorts with a chunk heel, but that feels a bit stale at the moment. Right now, it’s all about casual wear. Sport those casual, flat sandals and call it a (summer) day.

Outerwear To Go With Shorts

Shorter tops and tucked in shirts calls for shorter outerwear as well. Get a jacket or sweater that hits mid-hip or shorter for the most flattering silhouette. Another choice is a long cardigan. I love a calf-length or longer cardigan with a pair of shorts. It’s eccentric, yet chic. I also love using oblong scarves, aka shawls, as my outerwear in the summer. Not only will the right oblong scarf keep you warm in air conditioning, but you can also use it to protect your skin from the sun without overheating. Plus, a scarf can be folded up easily and stowed in your purse when you’re over it. (For tips on how to wear a shawl see my post, here.)

Caslon Linen Shorts

best women's shorts
Caslon $49

These Caslon Linen Shorts are an absolute favorite of my clients. They are comfortable, flattering, and a little sexy. These shorts come in several gorgeous colors besides the olive green. Just keep in mind, true to linen form, they wrinkle a lot.

Kut From The Kloth Gidget Denim Shorts (In Stimulating)

women's shorts
Kut from the Kloth $59

These Kut From The Kloth Gidget Denim Shorts in Stimulating are a great way to do a shorter short with a frayed hem that still looks put together and “clean.” A client of mine who absolutely abhors shorts, loves these shorts. She was shocked by how flattering and comfortable these shorts are. They are available at Nordstrom, Kut from the Kloth, Amazon, and Zappos.

Madewell High-Rise Denim Shorts in Danny Wash

flattering women's shorts
Madewell $74.50

The Madewell High-Rise Denim Shorts in Danny Wash are a great darker wash option of the shorts I am pictured wearing above. That high-waist is fantastically flattering and the comfort is amazing – of course. You know I am not recommending anything uncomfortable, but it bears repeating.

1822 Denim Distressed Cuffed Denim Shorts

flattering womens shorts
1822 Denim $39

These 1822 Denim Distressed Cuffed Denim Shorts are the perfect light wash denim short this summer. You will notice that I have a lot of cuffed shorts on this list. That’s because a perfectly cuffed short makes the thigh look slimmer.

Liverpool Chloe Pull-On Bermuda Shorts

flattering womens shorts
Liverpool $59

Here’s another pair of cuffed shorts that are a little longer in length for those of you wanting more coverage. The Liverpool Chloe Pull-On Bermuda Shorts also have a pull-on elastic waist making them even more comfortable.

Alice + Olivia Dylan High Waist Pintuck Shorts

best women's shorts
Alice + Olivia $195

These Alice + Olivia Dylan High Waist Pintuck Shorts are super flattering for those with wider or athletic thighs. I had my tailor take the shorts in for myself to accommodate my thinner thighs. I will say though, if you have wider hips or a bigger bum, these shorts will not work for you – the pockets start to pull unfortunately. These shorts are available at Nordstrom, Bloomingdale’s, Farfetch, Revolve, Neiman Marcus, Shopbop, and Alice + Olivia. They’re also available in a gorgeous burgundy color, here and here.

Alice + Olivia Donald High Waist Shorts

flattering womens shorts
Alice + Olivia $265

Like the other Alice +Olivia shorts featured above, these Alice + Olivia Donald High Waist Shorts are also flattering for those with wider or athletic thighs. But don’t forget, your tailor can also take them in for a slimmer fit like I had done. Same as the shorts above, wider hips or a larger bum won’t be flattered by these shorts. These shorts are available at Nordstrom, Saks 5th Avenue, Neiman Marcus, and Alice + Olivia.

Madewell High-Rise Denim Shorts in Malden Wash

women's shorts
Madewell $69.50 $39.99

The Madewell High-Rise Denim Shorts in Malden Wash are the shorts I cannot stop wearing. I’ve been wearing them two warm weather seasons in a row. I adore the light wash, the flattering fit, and the comfortable stretch. You can see them on me in the post, Can I Wear Yellow? They’re also available in a slightly different wash, here.

Athleta Trekkie North Short

most flattering womens shorts
Athleta $59

The Athleta Trekkie North Short is very flattering for wider thighs. It’s also amazing at flattening the stomach and creates zero muffin top.

Baleaf 5” High Rise Butt Lifting Pocketed Yoga & Workout Shorts

womens shorts
Baleaf $25.99

I had to add these Baleaf 5” High Rise Butt Lifting Pocketed Yoga & Workout Shorts to this list of flattering women’s shorts because they are just perfection. I wear them to work out or on walks, but they’re so flattering and comfortable I also wear them casually with a cropped tee and slim sneakers.

Joe’s Frayed Denim Shorts

best womens shorts
Joe’s $98

These Joe’s Frayed Denim Shorts are the perfect basic denim shorts for this summer. Order these and the Madewell shorts to compare fits and choose the one best suited for you.

Agolde Parker Vintage Cut Off Short

womens shorts
Agolde $128

These fabulous Agolde Parker Vintage Cut Off Short are extremely soft and comfortable.  They are available at Revolve, Free People, and Shopbop.

Sizing Tip: Order a size down.

Paige Mayslie Utility Shorts

women's shorts
Paige $169

Utility shorts are rarely flattering, but Paige has pulled it off. These Paige Mayslie Utility Shorts are available at Shopbop, PaigeRevolve, and Amazon. They’re also available in a blush pink at Nordstrom and Zappos.

Wit & Wisdom Ab-Solution Stretch Twill Shorts

most flattering womens shorts
Wit & Wisdom $58

Wit & Wisdom’s shorts are very kind to the stomach and thighs. These Wit & Wisdom Ab-Solution Stretch Twill Shorts come in several yummy colors including blue and an olive green.

Levi’s Ribcage Short

womens shorts
Levi’s $80

The Levi’s Ribcage Shorts are a little stiff, but still comfortable. These are for my clients who like structure in their denim. These shorts are available at Revolve and Zappos.

Baleaf Women’s 8″ High Waist Workout Exercise Shorts

womens shorts
Baleaf $23.99

At first, I was disinterested in the biker short trend, but then I saw these Baleaf Women’s 8″ High Waist Workout Exercise Shorts in burgundy. I love that they are sexy and sporty while also giving coverage for those who need it. These shorts are available at Baleaf and Amazon.

Madewell High-Rise Denim Shorts in Lunar Wash: Raw-Hem Edition

womens shorts
Madewell $69.50 $54.50

I adore the rich black color of these Madewell High-Rise Denim Shorts in Lunar Wash: Raw-Hem Edition. As usual, they are flattering and comfortable. These shorts are available at Madewell and Nordstrom.

Sizing Tip: Order your usual size as well as a size up to compare.

J.Crew 7” Stretch Women’s Short

women's shorts
J.Crew $49.50

The J.Crew 7” Stretch Chino Short is fantastically comfortable and offered in a variety of colors.

Sizing Tip: Order two sizes on this one: your usual size and a size down. This short traditionally runs bigger, but J.Crew has been messing with its sizing lately.

Kut from the Kloth Gidget Denim Shorts (In Consolidated)

women's shorts
Kut from the Kloth $59

I know I’ve already shown you numerous pairs of flattering women’s shorts, but I just have to show you one more color from Kut. These Kut from the Kloth Gidget Denim Shorts In Consolidated are a great medium blue option in a more casual look.

Sizing Tip: Order your usual size as well as a size up to compare.

Kut From The Kloth Catherine Boyfriend Cutoff Shorts

women's shorts
Kut from the Kloth $69

These rugged Kut From The Kloth Catherine Boyfriend Cutoff Shorts are flattering and provide stretchy comfort. These shorts are available at Kut from the Kloth, Nordstrom, and Zappos.

Sizing Tip: Runs true to size, but also try on a size up. Unlike most boyfriend looks, this one seems to run a bit small.

NYDJ Slant Pocket Utility Shorts

flattering women's shorts
NYDJ $79 $47.40

The NYDJ Slant Pocket Utility Shorts are one the most flattering pairs of women’s shorts, and this saturated shade goes with almost everything.

Loft Riviera Shorts With 4 Inch Inseam

women's shorts
Loft $39.50

The Loft Riviera Shorts With a 4-Inch Inseam have been on my list of go-to women’s shorts for years. They fit athletic thighs nicely.

Sizing Tip: Runs big, but is not reliable. Even a change in color will alter a fit. I always say order two sizes from Loft: your usual size and a size down to compare.

7 For All Mankind High Waist Cutoff Denim Shorts

women's shorts
7 For All Mankind $145

I love the sage shade of these 7 For All Mankind High Waist Cutoff Denim Shorts. Enjoy some inner thigh coverage with these chic rustic shorts. They are available at Neiman Marcus and Saks 5th Avenue.

The Great Vintage Army Short

womens shorts
The Great $235

I adore these The Great Vintage Army Shorts. They are so coveted they are about to sell out completely, but I couldn’t resist sharing them with you. Hurry, and get the last ones!

Treasure & Bond Utility Shorts

womens shorts
Treasure & Bond $69

Pair these uber comfy Treasure & Bond Utility Shorts with a bodysuit or other fitted top.

Sizing Tip: Size down to get a slimmer fit.

L’Agence Ryland High Waist Shorts

womens shorts
L’Agence $198

These L’Agence Ryland High Waist Shorts are freakishly soft and run large. Order a size down and enjoy the pajama feel.

Madewell High-Rise Denim Shorts in Tile White

best womens shorts
Madewell $69.50 $39.99

As you can tell, Madewell is my go-to source for flattering and comfortable women’s shorts. They just know what they’re doing. These Madewell High-Rise Denim Shorts in Tile White are available at Madewell and Zappos.

NYDJ Briella Rolled Denim Bermuda Shorts (In Cooper)

women's shorts
NYDJ $69

The NYDJ Briella Rolled Denim Bermuda Shorts in Cooper are one of the most flattering shorts out there. I love the way they provide coverage, but also have a fitted leg. I also love that they rise high enough to hold in any tummy. Plus, you will love the comfort. These shorts are available at Amazon, Nordstrom, and NYDJ.

Sizing Tip: NYDJ used to run large, but they are fitting more true to size these days.

Sanctuary Pathfinder Patch Pocket Stretch Cotton Shorts

women's shorts
Sanctuary $69

The Sanctuary Pathfinder Patch Pocket Stretch Cotton Shorts look so much better in person than they do in this picture. They are chic, cool, comfortable, and fun. You will not look like a Girl Scout — I promise.

Sizing Tip: True to size.

NYDJ Briella Rolled Denim Bermuda Shorts (In Rhodes)

women's shorts
NYDJ $69

Here are the NYDJ Briella Rolled Denim Bermuda Shorts in a lighter shade of denim. I am loving lighter denim since it pairs so well with navy and feels really fresh when paired with lighter colors. These shorts are available at NordstromNYDJAmazon, and Zappos.

Sizing Tip: NYDJ used to run large, but they are fitting more true to size these days.

Loft Scalloped Shorts With 4 Inch Inseam

women's shorts
Loft $49.50

These Loft Scalloped Shorts With A 4 Inch Inseam are the most feminine of the women’s shorts listed. They may be too cutesy for most of you, but I had to add them to the list because they fit wider hips and larger thighs beautifully! They look especially great on shorter women.

Sizing Tip: True to size, but order a size down as well just in case.

Wit & Wisdom Ab-solution Denim Shorts

women's shorts
Wit & Wisdom $58

Wit & Wisdom is very kind to the stomach and thighs. They have a whole series of shorts with a flattering fit, like these Wit & Wisdom Ab-solution Denim Shorts.

Sizing Tip: Wit & Wisdom runs a touch big. I recommend ordering your usual size, and a size down.