Every year I try to find the shorts. You know, the ones to wear with everything…the unicorn of denim shorts that are comfortable but not frumpy, can be dressed up for dinner or thrown over a suit for the beach. The ONE pair I’m willing to spend money on because of price per wear. That pair.

Every year I order a ton of shorts to try on and end up sending them all back in frustration. Too high, too tight, too rigid, too short, too…something. This year has been no different…I try on all the pairs, get frustrated, wait a couple of weeks and do the whole thing over again. It’s the same cycle over and over again and it’s maddening.

Bye, High Rise. Let’s Try Mid-Rise Denim Shorts

I don’t want rigid denim for my jean shorts. I just don’t. I want softness, I want comfort, and I don’t want a tight high rise that goes up to my boobs and is short enough for my butt to peek out. I don’t want to have to break them in. I don’t want to feel the rigid denim digging into my stomach and thighs every time I sit down. I don’t want to have to wiggle my way into and out of them…I don’t want any chance of my bikini bottom accidentally sliding off at the beach as I pull down my shorts. Just–no. I am over it, at this point. I’m turning 40 soon, have zero f%$ks to give and want some darn shorts that work.

But, I had try to on a bunch of shorts that didn’t work before I found the ones that did.

Spoiler alert: My favs are still the shorts I’ve been wearing for years (click to jump down to that section of this article).

1. The Cutoffs That Gape At The Waist | Free People Loving Good Vibrations Shorts

Free People Loving Good Vibrations Shorts (28)

I so wanted to love these–they look like everything I want in denim shorts: not too high of a rise, great fraying at the hem, perfect distressed wash. But they aren’t made for big booties. The 28s were too tight across the bum and too big in the waist. I tried the 29 but they had weird excess fabric in front. These would be great for someone with less curves and I LOVE all of the colors they come in so I was so bummed they didn’t fit.

2. The Pair With The Stiff Zipper | Free People Curvy High Waist Denim Shorts

Free People Curvy High Waist Denim Shorts (28)

So I thought maybe the curvy pair from Free People would be better. Room for a booty and won’t gap at the waist, right? And while they felt OK, I didn’t love the way they looked. The zipper was super stiff and had WAY too much excess fabric that made it stick out (you can see in the second pic). No.

3. The Pair That Are Fine But Run Small | MOTHER the Dutchie Shorts

MOTHER the Dutchie Shorts (28, more sizes here) | t-shirt(m)

I did like these MOTHER shorts, but they were a bit too small in my regular size, and I didn’t LOVE them enough to justify that price. They were fine. But over $200 is way too much for I guess these are ok. They have to be fabulous at that price.

4. The Other Shorts With The Super Thick Zipper (Why??) | Good American Bombshell Cutoffs

Good American Bombshell Cutoff Denim Shorts (6)

I have (and love) a pair of Good American’s Bombshell shorts, but this version wasn’t the best. They definitely fit on curvier bodies (they fit both across the bum and in the waist), but again with the super thick zipper that creates extra bulk across the belly! Why??

5. The Ones With The Drafty Bum | Good American Good Curve High Waist Denim Shorts

Good American Good Curve High Waist Denim Shorts (6)

I hadn’t yet tried the Good Curve fit and was interested to find out if I could roll that front roll down or if it was sewn like that–and it’s sewn like that. Bummer. I did like the high-low hem and the slit at the side for extra movement, but the back just kind of felt…drafty. Even though they weren’t crazy short it felt like my entire bum was hanging out of them.

6. The Ones I’ve Been Wearing For Years (Size UP) | AE Ne(x)t Level Denim Midi Shorts

AE Ne(x)t Level Denim Midi Short (10) | t-shirt(m)

I finally went back and tried the midi shorts I’ve been raving about for years–they change a bit from year to year, but the result is always pretty much the same: soft, stretchy, not-too-short but not-too-long, cute & comfy shorts to wear with all the things. The key?? SIZE UP. I made the mistake of forgetting this and ordered my regular size 6 this year. Um…don’t make the same mistake. I actually tried a 6, 8, 10 and 12 and found the 10’s were the perfect fit. (I also wore them in size 12 when I was pregnant!) These are great–NOT high-rise, not super low, just comfortable jean shorts that are also cute. Oh, and they’re the least expensive of the bunch–SOLD.

7. My New Favorites | AE High-Waisted Denim Tomgirl Midi Shorts

AE High-Waisted Denim Tomgirl Midi Short (8) | t-shirt (m)

I came across this pair when I was ordering my favorite midi shorts and couldn’t resist trying them as well–that wash and that distressing is everything. Relaxed but not loose–with a slightly longer inseam for more coverage. Sounded perfect! I tried multiple sizes in these as well and found that they run a bit bigger than the midi shorts–an 8 was perfect. Unlike the midi shorts, these have no stretch but the denim feels broken-in and softer than the other rigid denim shorts I tried. LOVE.

XOXO,

Scotti