I don’t know what it is about shorts, but I have a very, very hard time a) shopping for them, b) styling them, and c) actually leaving the house in them. It’s hard for me to feel like myself in them - I usually either feel like I’m trying to come off as a teenage camp counselor, a frumpy tourist on a cruise ship, or a Coachella attendee. No bueno.
However, unless you’re committed to finding alternatives to shorts (Fancy Mom post on this incoming this weekend), or you’re OK with sweating your ass off, shorts are inevitable. Here’s how I’m wearing them for everyday, totally normal activities - nothing tricky, nothing over the top, just easy peasy shorts.
LONG DENIM SHORTS
These are my go-to style. I love long, baggy denim shorts - nothing about them says anything other than relaxed middle-aged woman. They can look elevated or casual, interesting or boring, they are *perfect*. These are mine. I went to Santa Barbara this past weekend, and these + a button down, a bikini, and one dress were all I packed. I wore these nonstop.
I love them with an easy navy sweatshirt and black leather sandals for everyday running around.
No surprise, they’re great with a boxy, cropped structured tee.
And here, with a baggier, softer, oversized tee (which I should have steamed…). With something like that, I try to go with a shoe that is a little more feminine, and has some structure - like these Dries red wedges, or these Row flatforms. This long sleeved striped shirt would also be terrific here - I have this and I wear it at least once a week.
Here’s how I’ll be dressed every day this summer - I love a button down with these, but it’s important to unbutton the bottom few buttons, and also the top few, so just the middle two or three stay closed. If you leave the bottom ones buttoned it gives a weird stiffness and formality. Leaving them open makes it all feel personal and comfortable and casual. This is my button down - in Grecian Blue. I also really love this one in light pink. These are my loafers, but these are perfect too.
Just for fun, here they are with a fitted blazer worn as a top (mine is very very old, but this one would be great). These are the Khaite beaded sandals I love - the color and the heel height are both a dream for summer, and the little bag is vintage Valentino from TRR, but here are some similar vintage options.
SPORTY SHORTS
I loooooove these groovy little shorts. They have a very very distinct dELiA*s vibe - they’re so excellent, and when I wear them, I really kind of lean into that early 00s feeling, but in a more grown up way. Because there’s so much going on with them, I prefer to wear them with a clean white tee, and these very on-the-nose jelly flip flops. I got this hat in Santa Barbara over the weekend at a beach shop, but this one is similar. It keeps the sun off the upper 45% of my body, which is a WIN and I think it’s cute.
Another sporty style I love are classic Umbros - I got these last summer, and theyr’e super comfortable, easy to roll up to make them shorter or longer, they dry quickly, look cute with a swimsuit…. they’re inexpensive….I just love them. If I’m wearing them out and about I like them with a more polished or formal top. This one is High Sport, but I also love this one - it’s a stretchy swimsuit material and looks way more expensive than it is. The bag is from Savette - isn’t it perfect?!?! Kind of prissy, ladylike 90s, but also modern and minimal. A joy.
One of my very favorite resources for shorts are men’s swimsuits from Dries - I love them. This is a size Large, but they have the most beautiful prints, are super special, comfortable, quick dry, all the things you want in summer shorts. I like them best with another print or patterned top - this camp style knit is from Róhe, and I like leaning into the masculinity and dad-ness of it with these grey New Balances.
But if that camp knit is too much, a simple stripe button down is also gorgeous here.
PREPPY KAHKI SHORTS
I have a very hard time styling this kind of short - and yet, I always want to wear them. These are Aritzia. They remind me of the kinds of shorts the cool girls wore when I was in middle school and high school, very clean girl and preppy, and I think that’s why I struggle with them. But rather than try and change their DNA and make them weird and cool, for this I kind of leaned into that. The shirt is from Matteau, and I like it as an alternative to a collared polo. It’s great with a tiny itty bitty Chanel crossbody, and then a pair of black Mary Janes pushes it into more French girl feminine territory than mid 00’s prep. I’m wearing these, but I also love this pair.
So when I was in high school, halter tops were a thing - in the video I thought maybe it was an Old Navy thing but I think it was Abercrombie. Anyway, I got inspired to try a halter top with these shorts, but mine is Dries (try this one instead, mine is sold out). I’m weirdly into this! I think the print of the halter and the colors work nicely with the shorts, and it kind of skims the surface of being a really corny tourist in a tropical resort look, but because it’s Dries and the print is sophisticated, and these Row flatforms are so great, it looks cool. I’m not sure I’d actually wear this out of the house, but I like it.
Meanwhile, it’s hard to argue with the shorts and a navy sweatshirt and loafers. This is how I’ll style these this summer - very Dad.
Ok, everything else is so practical practical realistic - here’s one that’s just fun. I recently got this sequin snakeskin shirt from Dries (now 30% off) and I love how it looks with these shorts. Kind of like a disco Steve Irwin - and I’m just totally in love with these Row shoes, I’m wearing them all around the house with socks to break them in. It doesn’t make any sense, but it works - the colors blend nicely together, and the shirt (while insane) is a very classic shape, so it’s not overly jarring with the shorts. I just love it so much.
So that’s it.
I get into this at the end of the video, but I do want to say - I’m not proclaiming these shorts trends or these are the must-have shorts. These are the shorts I feel comfortable and like myself in this summer. Some are long, some are very short, but both lengths work for all bodies - if said bodies want to wear them. The first step to making an outfit “work” is liking it, and if you really like it, that will get you about 75% of the way there. If you don’t actually like it, don’t force it.
But one way I do think about styling things like that, which might be short or show a lot of skin - if the shorts are short, the top should be loose and/or boxy. If the shorts are long, the shirt can be either oversized or fitted, the world is your oyster there. Shorts are tricky, and more than many other categories they’re tied up in a lot of body myths and weird feelings. I feel like I should say this at the end of every letter, but this one specifically - I hope I’ve given you some ideas, but at the end of the day, you do you baby!
I love you!
Your friend,
Laurel
Share this post