Style Out #1: The Long and Short of It
5 pairs of Bermuda shorts, 25+ ways to wear them this summer
This letter is too long for email. Read on the Substack app for a seamless experience. Oh, and apologies in advance for all the short puns. I couldn’t help myself :)
Hi friends,
I hope you’re staying cool and safe wherever you are this holiday weekend.
Since real summer weather doesn’t actually descend upon SF until September (thanks, Karl the Fog), I found myself yearning for the trend I’ve considered to fully participate in this season: the Bermuda short.
I’ll be honest, I’ve been hesitant to wear Bermudas since they started cropping up again last summer, as I’m not exactly blessed in the height department at a mere five foot three. But I do love a challenge, so I set my sights on finding five different pairs to style for this letter.
I’m a big believer in simple but interesting outfits for summer (year-round, honestly), which I recently wrote about here. You’ll see the different styling levers in practice, and I can’t wait to find out which looks resonate the most! I’ll be waiting in the comments.
The Tailored Wool Short
Featuring: By Malene Birger Cymbaria Short (alt here and here)
We’re starting off strong. A tailored, high-waisted short with a full front pleat and a hem that hits well below the knee is, objectively, one of the trickiest styles to wear.
I’m gonna be technical for a moment — a Bermuda is a straight short (from waistband to hem) that hits just above the knee, whereas a voluminous short that goes past the knee would be considered a culotte by some serious fashion people. But for the purpose of this letter, we’re calling these shorts a Bermuda, k?
The pleats and the tailoring give off that I-have-back-to-back-meetings vibe, but it’s still technically a short, so I leaned into that push and pull.
I’m so in love with my new Anteros top! It has a chic asymmetrical hem that’s lovely on its own, but I tucked it in to keep the eye from traveling straight down the hem. The high contrast pairing (butterscotch with black) instantly creates definition at the waist.
A pointy kitten mule or a nude mesh flat that show plenty of skin would also work but I love the unexpected vibe my Tibi sandals (a recent TRR score for $100!) bring to this outfit. The bright white keeps the butterscotch and black from feeling flat, and the barely there straps with the angular heel are just cool.
If your legs are on the shorter side, I’d avoid thicker ankle straps as it can visually cut off your frame. BTW, please take my styling notes as suggestions, not a hard rule. I believe in wearing whatever you feel good in! I certainly did with the outfits I styled here.
The knot serves as the waist-defining tuck in this look. I wanted to make the Bermudas feel less serious so I mixed my textures (crisp poplin with soft crochet) to create that unexpected vibe.
I went for my favorite shoe of the season, my well-worn wedge mules with a cool asymmetrical silhouette and architectural heel to add some height and a touch of edge. A slimmer thong kitten heel also works here to elongate the legs.
My Elaree beaded bag ties it all together with an extra touch of texture.
Another great option is a slightly shorter top (or even cropped) because it instantly defines the waist sans tuck.
I love a classic black and white combo, but opting for lavender against black turned out to be an unlock. It creates a softer contrast compared to stark white, which reads calmer but still refined.
We all need more whimsy in our outfits so I added a pop of red at the bottom (OFELIA shows us even more ways to wear red sandals here). I went for deep brown accessories to add texture and ground the whole look.
If your torso is on the shorter side, a tailored top with some volume creates the illusion of length up top and reads streamlined overall. The subtle peplum and pleats both carry volume in different places: the top flares at the waist whereas the short opens at the hip. I live for a clever play on proportions that feels considered rather than accidental.
A nude-ish shoe like my Jude mules creates even more length at the bottom, and a minimal pouch keeps things understated.
A graphic sweatshirt with a tailored short should feel confusing but as Ayo Edibiri (styled by your stylist’s favorite stylist, Danielle Goldberg) showed us in her trousers and graphic tee version, the result is nothing short of cool. There’s enough structure to hold the entire outfit together so your top can be as casual and offbeat as my well-worn Anine Bing sweatshirt.
I went for multiple contrasting elements here — relaxed sweatshirt against the tailored short, textured straw bag against the patent leather sandal with hardware — but they don’t feel chaotic since everything stays in the same neutral palette.
The Easy Silk Short
Featuring: Eaves Loretta Silk Short (alt here and here)
On paper, a pull-on silk short that hits just above the knee is the easiest pair to style in this lineup. But the fabrication, in practice, is what makes this pair tricky. Silk reads dressy no matter what you do with it, so the instinct is to fight that and dress it way down (with a t-shirt or tank top), or lean so far in that it tips into taking itself too seriously.
Every look I styled around the Eaves short (it has pockets, btw!) either meets the silk where it is or pulls it back just enough with something more casual, without sacrificing refinement. And somehow I ended up with a black, white, and red color story here, which feels very much like me.
This outfit is straight up silk on silk but I wanted to make it more interesting so I tucked my Rohe cami asymmetrically. The black lace layered over the white silk instantly creates contrast through color and texture, which takes this look into going-out territory. In my humble opinion, this is the kind energy a silk short can handle that a cotton one couldn’t.
I kept everything else neutral so my cute lil phone trug/mini basket from Underwater Weaving gets to shine and add an extra dose of texture. And to keep things grounded, I went for a minimal sandal instead of a heel.
I usually reach for a button-down as a summer layering piece, but my thrifted trench turned out to be the better proportion unlock. It elongates the whole look because the hem sits just slightly longer than the short. To create definition at the waist, I opted for a Flore Flore tee that hits right at the waistband of the shorts. I went with off-white for a softer contrast that also bridges the red and black together.
My favorite leather flip-flops keep the whole thing from taking itself too seriously, which feels right for rocking a silk short on a Monday. And my Le Sundial mother-of-pearl necklace ties everything together without taking over.
I wanted to style a little short suit situation with my recently acquired vintage Moschino blazer from SPRL, which, not gonna lie, I wanted to gate keep so bad. It’s been my go-to for an impeccable assortment of curated (and affordable!) vintage these days, and I’m so impressed with how Alice Watts and acdlt have thoughtfully selected their vintage partners. No need to scour pages and pages to find the good stuff because every piece on SPRL is a gem. (Not sponsored btw, I just love supporting small businesses I believe in.)
OK, back to the outfit. Pairing my perfectly tailored vintage cotton blazer with the silk short was the right move. Silk on silk would have been too serious. If the occasion calls for it, you can dress it up more with a pointy kitten mule but I love the more relaxed vibe of a strappy sandal. The pop of red, wood tassel clutch, and my fave Sophie Buhai fringe earrings add just enough personality to the whole look.
I recently wrote about mixing different textures to make a monochromatic outfit pop, and this is almost the exact look I used as an example. I like to practice what I preach.
Let’s break down the textures at play here: linen asymmetrical top + silk shorts + leather sandals + nylon-satin bag + mother-of-pearl pendant necklace. So chic, simple, and interesting!
This is my most casual take on the silk short, focusing on color and texture. I love the contrast of the Suzie Kondi terry sweatshirt against the black silk. The Tibi sandals brighten things up and the basket bag adds more texture.
The Pull-On Poplin Short
Featuring: The Anteros Coen
I’d been patiently waiting for the restock of the Coen shorts from The Anteros, and it was well worth the wait. I can’t get enough of this fern green (Bryn Rhoads is a color genius), the easy drawstring waist, and an inseam that’s genuinely democratic (5.5” to 6.5” depending on size.) Oh, and it has pockets!! My only regret was not getting it in white in my size fast enough.
In my opinion, summer is the best time to experiment with color, so I immediately pushed myself out of my comfort zone with this pairing. Both butterscotch and fern lean on the warmer side so this combo feels harmonious. I skipped the tuck to show off the asymmetrical hem, and the color blocking still streamlines without it.
I added my silver Juju Vera earrings to keep the whole look from leaning too warm and the white sandals do the same. My Marlies Grace clutch grounds everything. Safe to say, this outfit was a hit with Levi — 5 paws all around.
Here’s another great example of intentional proportion play. The long shirt dress is doing so much more than your typical oversized button-down. The t-shirt hits right at the waistband while the drawstring cinches just enough to create definition, so even with all that length on top, the waist doesn’t disappear.
A pendant necklace adds a focal point right at the center of all that cream, drawing the eye up before the green short takes over below.
I styled it a few different ways for a summer beach vacay. I tied my old silk Matteau pareo like a scarf top and paired it with barely-there sandals and a wood tassel clutch for a dinner look. For the beach, I love an open cotton knit thrown over a swimsuit and shorts. If it’s too hot and humid out, ditch the layer and show off that bod. Every body is a summer body!
This shade of green is more versatile than it looks. Brown and cream are a given since they’re in the same warm, earthy family. But the purple surprised me too. It just works, and it comes down to the fact that green and purple both have blue in them, so they neutralize each other.
The Low-Waist Denim Short
Featuring: Still Here Cool Shorts (alt here and here)
The cool shorts from Still Here has a low-waist, a drawstring instead of an actual waistband, and it’s PINK. What was I thinking?! I did say I love a challenge.
The low waist and drawstring mean tucking is off the table. Tops that are long enough to hit just above the hip are your best friend here.
Don’t forget, a swimsuit is also a top! A one-piece elongates the torso, which is exactly what you want with a low-waist short. And the trick with a soft pink is to treat it exactly like white. Pairing it with black reads as classic contrast instead of a color statement. Hot pink would be an entirely different conversation.
Left: Swimsuit layered under a sheer, lightweight shirt for a daytime look. The dark shirt against the pink short keeps everything grounded, and the A.Emery flip flops make it feel exactly as casual as it should. My Laoli citrine necklace adds a warm note against all that dark.
Right: Shirt becomes a shawl, flip-flops swapped with a sleek sandal, and now it’s an evening look. I added my Juju Vera turquoise collar and Cordera beaded bag for a touch of personality.
Red and pink is a bold combo, and the ivory cami is key here. It gives the eye somewhere neutral to land and bridges the two non-neutrals. The sleek black sandals toughen up and ground the whole outfit.
Left: Suzie Kondi terry sweatshirt tied around the waist to create some definition. This is the move if you’re not fully committed to a red and pink combo. Plus, the knot covers any exposed skin with a low-waist short.
Right: Sweatshirt goes on and the ivory cami becomes the buffer between the red and the pink. It also creates the illusion of length up top. The lace hem peeking under the sweatshirt adds texture and a little unexpectedness without any extra effort.
Surprise — pink and yellow works too!
We’re using the same logic as before: treat the pink like white so the butterscotch reads as a warm, sunny combo rather than a bold statement. The white sandal cools everything down just enough. Also, the Anteros top worn untucked is perfect since we’re working with a low waist.
The Novelty Knit Short
Featuring: Pepa Pombo printed knit shorts (alt)
I’m really glad I got these knit board short-esque pair last summer, and can’t wait to rewear them this season. Pepa Pombo is a Colombian luxury knitwear label that’s been doing this since 1978. Every piece is made in-house with three-dimensional texture as their signature. They’re not exactly everywhere yet, which is part of the appeal.
This pair comes with its own set of challenges: the bold print, the knit fabrication, and the board short silhouette. The trick is to let the short anchor the outfit and build everything else around it.
Instead of adding more white, I opted for a softer butter yellow tee to tone down the print. A sleek suede kitten heel dresses up the shorts and adds some texture. The beaded bag also creates textural interest and echoes the print without competing with it.
A sheer, oversized ivory shirt is the best thing you can throw on over this short because it softens the contrast without covering up the print.
Left: A pop of purple and green feels a bit risky here, but they actually work because the eye has somewhere else to land. I’d wear something like this for a daytime vacation look.
Right: Swimsuit as a top again for an evening vacation outfit. The square neckline instantly adds some refinement to the outfit. A pop of red at the bottom gives the eye somewhere to go besides the print.
Left: Adding more black actually tones down the print rather than competing with it. I went for a Flore Flore halter to keep it simple and a neutral basket bag to add some texture.
Right: The lavender cardigan over the halter neck softens the contrast just like the butter yellow tee and sheer ivory shirt. I took another risky move with the pop of red here. Lavender and red works because they lean cool just like the black and white print.
If you’ve made it all the way here, phew, thanks for sticking all the way through!
I’d love to know which pair of shorts surprised you most. Drop it in the comments. I also scoured the web for more Bermuda options here.
And if you’re looking at these outfits thinking “I could never pull that off” — that’s exactly what I can help with. A Styling Session is one hour and we can work through whatever’s feeling stuck.
Chat soon,
Angela