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Five EHD women, not a single one in shorts…yet. But fear not, because this post IS about shorts as the headline suggests. Emily is basically the cut-offs queen, but almost no one else around here was a regular short subscriber and we all thought it’d be fun to go on a try-on session to see if we would convert ourselves (and pass on any recommendations to you guys to aid in your own search). I’m pretty sure as this specific photo was snapped, I was saying “YAY SHORTS” and this was the outcome. WE WERE EXCITED (or at the very least feigning enthusiasm to hide our terror of showing our human limbs on camera because evidently that’s a thing). Fueled by the promise of Shake Shack for lunch—though Veronica and Ryann ended up at In-n-Out, rude—we hit up The Americana in Glendale (for anyone not familiar, it’s one of those big outdoor malls with stores like Nordstrom, Madewell, Anthropologie). It also has a 24-hour Sprinkles cupcake ATM, but that has nothing to do with this post.

Everyone’s assignment: go try on a bunch of bottoms at several stores and report back on any you actually like/could see yourself buying. The good news is everyone actually found things they truly liked (and some of us purchased) and no self-deprecating words were allowed. Read on for what everyone picked and why, and then, pretty please, pass on any of your own suggestions for well-fitting shorts you can personally endorse.

Let’s do this. (But first, props to our photog Veronica who had to capture us in and around fitting rooms in “very flattering” fluorescent retail lighting.)

Arlyn (Editorial)

Shorts Relationship Status: Uh, definitely complicated. I’m only now, 34 years into my life, mostly unconcerned about whether my legs look like ham hocks or not, so this is a step forward for me and VERY freeing, particularly in hot LA summers. I’m petite and curvy, so there’s always an issue with inseam and rise. I can never seem to find the right combo. I also struggle with the “crotch stuff” (god, that was an unfortunate set of words together) when I walk in shorts, constantly tugging them down and mostly, it’s never worth it to me. 

Go-To Size: I’m a pretty solid 14/33, and fluctuate between L and XL depending on the brand/store.

Height: a statuesque 5’3″

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Pick 1: Pull-On Shorts, Madewell, $40

Size: L (though I also own in black in an XL and I prefer the smaller size)

Why I like them: I already own these shorts in black, so I knew I was grabbing them for this try-on session/shoot. THEY ARE THE BEST. At one point, we all had a color in our dressing rooms. It’s like wearing pajama bottoms, but the little slit up the side (which sadly you can’t see in my photo for whatever reason) and the material make them appropriate to leave the house in. My goal for the summer is to essentially collect them in every color and never stop wearing them. If you’re a shorty pants like me, the inseam and rise are PERFECT (plus, you can roll them down if you want and I promise no one will notice). 

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Pick 2: High-Rise Denim Shorts in Lunar Wash, Madewell, $70

Size: 32

Why I like them: Let me start by saying high-rise denim absolutely never works on me (I have a VERY short torso that is made to look even shorter with my exceptionally large bust), except these are probably magic because they were AMAZING. I tend not to spend a ton of money on shorts because I know I will never wear them but I walked out of the store with these and plan on actually wearing them, ha. They are flattening in the front poochy area (enough that I was confident enough to “French tuck” my T-shirt…this never happens), the perfect length for my short limbs, and have the perfect amount of stretch. I feel like I won the denim short lottery with these.

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Caitlin (Social & Partnerships)

Shorts Relationship Status: IDK. Like, would I wear shorts on a first date? Probably not. But did I find out about this shoot and then go home and eat cheese fries instead of like, prepping my legs and putting on some Jergens sunless tanner? Yup. Shorts will never be my first choice (especially when they ride up in the crotch, which I feel is a super common problem that we do not talk about enough! Is there boob tape for pants?) but yeah, I don’t mind wearing them if it’s hot. This is my long-winded way of saying that I have accepted that I have super pale and pretty thick thighs and I’m ambivalent about it now. 

Go-To Size: 30, L/XL

Height: 5’8″

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Pick 1: High Rise Denim Shorts in Lunar Wash, Madewell, $70

Size: 30

Why I like them: The morning we left to take these photos, I literally told Team EHD that I wanted to find high waisted shorts. Mission accomplished, y’all! These shorts are so comfortable, have the perfect “not too tight, not too loose” thing going on, and they were kinda like our Sisterhood of the Traveling Pants in that this cut looked SO GOOD on every single person who tried them on.

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Pick 2: High Rise Denim Shorts in Jordie Wash, Madewell, $72

Size: 30

Why I like them: Okay, okay, I KNOW these are technically the same shorts in a different wash, but hear me out: I have not worn actual blue denim shorts since…my sophomore year of college, probably? It’s been almost a decade and this was the first pair that reminded me that jean shorts could be kinda cute. I loved the wash, I loved the distressing, and you can cuff them up or leave them as-is, so you have some length options. Plus, I’m a Madewell loyalist (in the header photo, literally everything I am wearing is from Madewell) so I know that these will stand the test of time.

Caitlin Side By Side

Pick 3: Linen Blend Shorts High Waist, H&M, $20

Size: L

Why I like them: These are normally the kind of shorts I gravitate toward in the summer. I know it’s not traditionally flattering, but when it’s hot out, I do not want any fabric actually touching me and I love to rock the entire “my body is a cube” look with an oversized button-up and loose shorts—it’s kinda like my version of a muumuu. But y’all, this is even better than a muumuu because the pockets on these are NUTS. They are ENORMOUS. By my initial size estimate, I determined that I could definitely fit an entire burger in each pocket, which is so far BEYOND what I could ever dream for a pocket on a normal women’s short! Also, if you decide to eat a huge lunch while wearing these, they are SO STRETCHY and comfortable. Like, if I had to wear shorts to Thanksgiving dinner, I would pick these. Love ’em.

Velinda (Design & Production)

Shorts Relationship Status: We’re healing. When I was 14, my mom told me in the sweetest of voices that it was so cute she could see cellulite on my leg that was squished against a chair. I was barely post-eating disorder and I don’t know what it was she saw, but WHY WOULD YOU SAY THAT? (Moms! Don’t do this to your girls). I didn’t wear shorts again (only breathable day dresses on hot days) until I was 26 years old when I popped over to friends’ house in pajama shorts. One of my pals, who had obviously never seen my legs before, said “Velinda, you have great legs! Why are you hiding them?” So, I started to dabble a bit again, slowly building my comfort level. I think I kinda love shorts now that I’m in my 30s and finally sourcing confidence from me vs. whoever was last in my ear.

Go-To Size: 27, 4/6

Height: 5’8″

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Pick 1: High-Rise Denim Shorts in Erwin Wash: Cutoff Edition, Madewell, $70

Size: 27

Why I like them: So simple, but they have a little give which makes them really comfortable and not suffocating when sitting. Classic, casual and easy to pair in an ensemble.

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Pick 2: Levi’s 501 High-Rise Denim Shorts in Fault Line, Free People, $70

Size: 27

Why I like them: Apparently, I’m as attracted to tattered shorts as I am pants. Cheers to forever looking slightly like a vagrant. These rise a bit higher and are thicker, giving some extra tummy support. As a result of being thicker, they have a little less give than the Madewell pair, but I still found them to be comfortable and a bit “cooler.”

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Pick 3: Levi’s 501 Cutoff Shorts, Free People, $70

Size: 27

Why I like them: These were my favorite…on the shorter side, but still covered the booty (keep in mind, mine’s not abundant). I’m most attracted to them because they’re different than anything I have and they made me feel sassy…but I bet they could also go “chic” if paired right. Anyway, I liked the edge.

Jess (Editorial)

Shorts Relationship Status: Arch Nemesis?? I only own one pair of shorts that I have worn once in the past year and on that day I couldn’t wait to get my jeans back on. The constant adjusting, the inevitable chafe and cellulite show make me stay far far away from these little nightmares. Even in my younger (and thinner) days, I was always VERY uncomfortable in them (because the chafe is REAL people). This girl just has some genetically round-shaped thighs that have and will always be with me despite any past or future size. So when we were asked to participate, after my initial panic of the idea of wearing shorts ON THE INTERNET, I decided to get over my issues (because no one cares but me) and see if there was a magical pair of shorts I could like and feel good in.

Size: 30, on average

Height: 5’3 3/4″

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Pick 1: High-Rise Denim Shorts in Jordie Wash, Madewell, $72

Size: 30

Why I like them: I really liked these a lot and seeing me photographed in them kind of makes me want to go back and buy them. I considered going down a size to help with tummy support but liked the comfort of the 30. Also, the wash was 100% perfect.

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Pick 2: High-Rise Denim Shorts in Tile White, Madewell, $70

Size: 30

Why I like them:

Ryann: “Jess, I think you should try on white shorts today.” 

Jess: “HAHAHA white shorts with this booty? not. happening.”

Well, Ryann was right and I was wrong because I loved them A LOT (as shown from the expression on my face). I let my fears get the best of me and that’s why you should always go shopping with friends to push you out of your comfort zone. Apparently trying on clothes won’t kill you. Now my only fear would be spilling on them which I definitely would because I am a mess that shouldn’t be allowed to have nice things. Also, I want to note that while I don’t think they look “bad” in this picture, they looked and felt GREAT in the store. All the girls were begging me to get them. Highly recommend these puppies.

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Pick 3: Denim Shorts, H&M, $18

Size: 10

Why I like them: What an unexpected gem. Aside from one pair a loooong time ago, I have never bought pants or shorts from H&M. I guess I didn’t have a lot of faith in their cuts and quality. Well, guess what? These fit great, I love the wash and that hint of distress. They felt a teeny bit on the shorter side but that may be because I am not used to wearing shorts. Plus, they were $18. Basically FREE! So I bought them because I really didn’t have a choice. It was a low-risk investment to get me on the shorts train. PS, I also bought four more colors of the shirt I’m wearing here and in the other two looks. It’s the perfect fit, feels/looks expensive with its linen material and so comfortable (and only $13 each). I’m wearing a medium which is pretty true to size for me.

Ryann (Editorial)

Shorts Relationship Status: I keep ghosting them, but then I come back for more after a few months (Yes, just like your horrible tinder date—I’m THAT guy). Lately, I have been into dresses that are more forgiving, but then I have moments where I really just want to wear shorts and a T-shirt and call it a day. I currently have one pair of shorts, so this little EHD research project was very apropos for me and my life. 

Go-To Size: 28-29 (size 30 in Levi’s)

Height: 5’8″

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Pick 1: Levi’s 501’s High-Rise Denim Shorts, Free People, $70

Size: 30

Why I like them: These feel very Emily Henderson (I am pretty sure she actually has these), which might explain why I quickly snagged that puff sleeve top to try them with. The fit is great and I love a distressed short so yes, I did buy them and have no regrets. I’ve had versions of this same short so many times over the years (and I’d still be wearing them had my weight not fluctuated), but the upside is I now have them in three different sizes and I know these are a lifelong staple for me.

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Pick 2: Curvy High-Rise Denim Shorts in Glenoaks Wash, Madewell, $70

Size: 29

Why I like them: I am unsure about how I feel about these longer shorts on me. I always see girls rocking the longer hem, but often feel very insecure about how my legs look in them. They make me feel short and stubby? I don’t know. But, I think if I would have sized up, I would like them more because that would create a relaxed fit. That said, these may be the most comfortable, breathable denim shorts I have ever put on my body. I feel like I can really DO things in these bad boys, I could even ride a bike in them (why I would be riding a bike I am not sure—but I could and that is all that matters). 

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Pick 3: Levi’s Vintage Shortalls, Free People, $98

Size: L

Why I like them: Man do I love these overalls. I grabbed them on the way to the fitting room, because the white wash caught my eye and I’ve been wanting shortalls for a while now. The only size they were carrying in store was Large, which I figured would be fine because I like an oversized look and when I put them on I knew immediately they are a HELL YES. They are very comfortable but still chic (IMO). I definitely feel effortlessly cool wearing them and can see them being a staple in my wardrobe. I would wear with long sleeves and boots, or short tees and sneakers. 10/10!

Team Opener

Alright folks, that’s a wrap on our shorts try-on session. We’ll leave you with a grid of photos of us in ALL THE SAME SHORTS that somehow worked on all of our bodies. WE LOVE THESE SHORTS. This was an insanely fun morning, so if you like this style of post, we’d love to do more for different clothing categories…let us know!

***photography by Veronica Crawford


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