Late Summer Casual Outfits: Softening the Transition
I love late summer in Brooklyn. The light shifts, the air gets that particular crispness at the edges, and suddenly all my heavy linen pieces feel too thick. That's when I start reaching for the in-between clothes — the late summer casual outfits that bridge the gap between sticky July afternoons and the first real sweater weather of October. It's not that deep. But also kind of.
Why Late Summer Calls for a Lighter Preppy Uniform
The preppy revival I keep writing about isn't about blazers and penny loafers worn in 90-degree heat. It's about taking the silhouette — the clean lines, the classic collars, the comfortable fit — and making it breathe. Late summer outfits should feel like a soft exhale. I'm talking loose oxford cloth shirts in cotton that hasn't been starched within an inch of its life, trousers that skim rather than cling, and colors that are a little washed out in the best way. Think faded navy, dusty sage, and the occasional pop of paprika or cherry red to remind you that fall is coming but you're not there yet. In fact, when I put together a late summer casual outfit, I follow one rule: if it feels stiff or precious, swap it for something you wouldn't mind spilling iced coffee on. That's the spirit.
Three Outfit Formulas That Actually Work
Here are three combos I've been rotating since August. They're all built around the same principle: comfortable, slightly undone, but intentional.
The Soft Rugby Shirt + Wide-Leg Jeans. I found a secondhand rugby shirt from Ralph Lauren in a faded forest green — $30 at a flea market in Greenpoint. It's thick in a way that feels substantial but not hot, because it's all cotton and the sleeves are cut generously. I tuck it loosely into a pair of high-waist wide-leg jeans (mine are Levi's Wedgie Fit in a light vintage wash, about $88 new). The trick is to leave the top two buttons undone and roll the sleeves once. I sometimes add a thin leather belt to define the waist, but usually I let the fabric hang loosely. For shoes, a pair of plain white Sambas or Reebok Club C 85s keeps the whole thing from looking like you're about to play lacrosse. This late summer casual outfit works for a coffee shop, a library study session, or a walk to the farmers market. It's not trying too hard, but it's clearly a look. I've also been layering a lightweight cashmere cardigan over the rugby on cooler evenings.
The Loose Button-Down + Tailored Shorts. When the heat insists, I swap jeans for shorts. But not just any shorts — I mean a tailored pair in a linen-cotton blend, maybe from J.Crew or Everlane, around $60-$70. The shirt is an oversized Oxford in pale blue, also secondhand, with the collar left flat and the sleeves rolled to the elbow. I add a thin leather belt that matches the color of the shoes (tan slides or leather sandals). And I always finish with a small shoulder bag — something manageable, like the Uniqlo half-moon bag ($19.90) or a vintage Coach crossbody. I wear my hair in a low ponytail or a claw clip to keep the neck cool. The whole look is effortless but feels like you actually got dressed.
The Knit Polo + Loose Trousers. This one came from a K-pop styling rabbit hole, and I'm still not over it. A knit polo (I've been wearing one from Mango that was $50, in a washed-out burgundy) paired with a pair of drawstring trousers in cream or beige. The fabric of the trousers is crucial: they should be lightweight but not sheer, with a nice drape. Uniqlo's wide-leg pants ($39.90) work, or if you want to splurge, Aritzia's Effortless Pants ($150) are great. The whole thing is soft, easy, and somehow reads as very intentional. I wear it with simple flats or clean white sneakers, and always roll the trousers slightly at the ankle. This late summer casual outfit is my current favorite. It works beautifully for a dinner out or a gallery opening — polished without being stiff.
The Little Details That Make It Feel Intentional
The difference between a good late summer casual outfit and a great one often comes down to two things: the bag and the shoe. I've been wearing a lot of straw bags — the kind that are structured but not rigid, from brands like Sezane or vintage finds. They add texture and lighten up heavier pieces. For shoes, I'm mostly in leather sandals (Teva or Birkenstock) or canvas sneakers (Superga, Vans). Avoid anything with a shiny finish; it reads as too polished for this transitional moment. Also, jewelry should be minimal — a small gold hoop, a thin chain necklace, maybe a single ring. One more thing: fragrance. A light, musky scent or a citrus cologne sticks well in the late summer air. I've been wearing Le Labo's Santal 33 or Glossier You. The goal is to look like you just threw it on, but in a way that clearly took thought. And yes, Coco has approved most of these combos by sitting directly on the folded garments while I'm getting dressed.
So that's where I'm at with my late summer casual outfits this year. They're soft, they're practical, and they let me ease into fall without the wardrobe whiplash. If you're still figuring out your own transition, grab a rugby shirt, a pair of good trousers, and a bag that makes you smile. The rest will sort itself out. Let me know which combo you're trying first — I'm always curious how these translate outside my own closet. — Ella
