Why Year-Round Shorts Are a Fashion Flex
From Ayo's "The Bear" fit to Bad Bunny's rotation 🩳, free the thigh, flaunt the knee—styling tips, shopping picks, and ideas for every season.
2024 flirted with structured shorts—2025 is ready for a full commitment. From leather shorts in January to tailored Bermudas in July, I’m supporting the liberation of our legs all year long.
❄️ Yes, I'm writing about shorts while NYC shivers... but hear me out.
What makes shorts so irresistible? It’s their mix of unpredictability and playfulness—effortlessly transitioning into a seasonless wardrobe staple. With their continued glow-up now including office-ready and red carpet-worthy styles, shorts have never been more versatile—or sexier.
My quest: Late last year, I set out to find the perfect year-round shorts that would complement my petite frame. I had a specific winter uniform in mind—one that hinged on the right moto boots, loafers, sweaters, layers, and, of course, the ideal pair of shorts.
A gifted pair of butter-colored, vegan leather H&M shorts had already become a wardrobe MVP, taking me from block parties to pop-ups, speaking engagements, and even Art Basel.
But for winter, I needed a darker counterpart—equally travel-friendly and versatile with shoes. I found my answer in a classic pinstrip find at Maje.
Here's how to master a range of looks:
The Perfect Length Formula
Micro: Hit 2-3" above mid-thigh (best for evening)
Midi: Graze the knee (office-ready)
Bermuda: Kiss mid-calf (ultimate sophistication)
Y2K Throwback: Low-rise, relaxed fit hitting right at the knee - think skater meets hip-hop culture. Channel that golden era of MTV with cargo pockets and wide-leg silhouettes
Year-Round: For our warm-weather friends, try silk-blend shorts that hit just above the knee. Light enough for tropical temps but polished enough for business meetings or dinner. Think resort wear that transitions seamlessly from beach to bistro
With monochromatic shorts looks, socks can be the supporting star.
Power Pairings
Winter: Chunky knits + tall boots
Spring: Oversized blazer + loafers + statement socks
Summer: Crisp button-down + minimal sandals
Fall: short-sleeved turtleneck bodysuit + knee-high boots + oversized leather jacket (optional)
All-weather: waistcoat + mule (even a kitten heel slingback if that’s your thing)
Fabric-wise? Give me camo chaos, denim in any state of distress, and leather that means business. Brands like Banana Republic's wool bermudas are office-approved and a go-to for warm weather.
As a leather girlie through and through, leather shorts are a non-negotiable in my wardrobe. They’re perfect for traveling with a hoodie, tee, and slip-on moto boots. When I’m home in cooler climates, I love pairing them with a chambray shirt, a turtleneck, and sheer tights. For linen blends that scream summer staple and have real staying power, Everlane and Ralph Lauren never miss.
My shorts hall of fame is deliciously diverse
Pharrell, the OG of short suits, walked so Jurnee Smollett could run in that electric blue Alexandre Vauthier couture (stilettos and all). Being ahead of the curve Michelle Yeoh came through in pastel perfection at the BAFTAs and did so with ease.
Now that the shorts trend has settled in, my shorts moodboard is stacked. It has everyone from TV characters to artists to random people on the street.
I, like many fashion fans on Reddit, fell in love with that look Ayo Edebiri wore in season 3 of “The Bear” (paired with a Commes des Garçon top). S/O to the costume designer, Courtney Wheeler. Off screen it was her blue-green suit she wore to the Inside Out 2 premiere that caught my eye.
Tyler, The Creator serves a daily masterclass in preppy proportions, while Pedro Pascal’s red and black Met Gala Valentino shorts look are still iconic.
Then there’s Bad Bunny, whose endless rotation of shorts—usually tropical and casual—delivers instant style inspo every time. There were a couple of moments where he was photographed in a more structured look and I wouldn’t mind see more of this variation.
My last word on styling: Think of shorts as a proportion game, not just a length play. Short? Go big up top. Long? Keep it sleek on top. And for all the skeptics - yes, shorts with tights is having its main character moment in 2025. 🖤
Now, check my shopping list: These shorts work whether you're just channeling Thom Browne himself or just trying something different...
Dreamy
Treat yo self
High style without the high price
What I’m loving
Men’s Fashion Week is here! Pitti Uomo wrapped, and Milan has begun. This post rewinds to a 1962 fashion show—a pivotal moment when classic tailoring met daring new silhouettes, and the roots of modern casual style began to sprout.
The Kody Phillips boxer shorts 🖤
I love this one! Def looking at 🩳 with new eyes!