women's shorts
Madewell $69.50 $59.50

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 a fabulous look — especially this summer. The selection is the best I have ever seen on the casual front. 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 looky dumpy. First of all, none of the shorts listed below will make you look dumpy. 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, bodysuits, or leotards. If you want to wear a longer top with shorts, just tuck it in, either fully or with 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, and sneakers. You can also rock an open-side 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 very chic and eccentric.

NYDJ Slant Pocket Utility Shorts

flattering women's shorts
NYDJ $79 $63.20

The NYDJ Slant Pocket Utility Shorts are the most flattering women’s shorts, and this saturated shade goes with almost everything. They are available at Nordstrom, NYDJ, and Bloomingdale’s.

Madewell High-Rise Denim Shorts in Malden Wash

women's shorts
Madewell $69.50 $59.50

The Madewell High-Rise Denim Shorts in Malden Wash are the shorts I am sporting this summer. I love the light wash, the flattering fit, and the comfortable stretch. These shorts are available at Madewell, Zappos, and Nordstrom.

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 three gorgeous colors: olive green, navy blue, and a beautiful rust. Just keep in mind, true to linen form, they wrinkle a lot.

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 that I’m thinking of wearing them casually.

7 For All Mankind High Waist Cutoff Denim Shorts

women's shorts
7 For All Mankind $99

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 Nordstrom, Bloomingdale’s, Zappos, and Saks 5th Avenue.

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. Like all the shorts on this list, they are flattering and comfortable.

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!

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.

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.

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 Nordstrom, Paige, Shopbop, Revolve, Amazon, and Zappos.

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.

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 $54.50

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.

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.

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.” These shorts are available at Nordstrom and Kut from the Kloth.

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

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.

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.

Madewell Denim Shorts In Tile White

women's shorts
Madewell $74.50 $54.99

These Madewell Denim Shorts In Tile White are my absolute favorite white shorts. They’re so stretchy and utterly stylish.

Sizing Tip: Run true to size, but the stretch can enable you to go down a size if you want.

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.

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, NYDJ, and Zappos.

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.

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. 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. 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.

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.