Late-Summer Dressing

The final weeks of summer hold a special kind of magic—a slow, sweet transition between the heat of July and the first crisp hints of fall. It’s a time when the air still holds warmth, but the light shifts and shadows stretch longer. 

The perfect moment to lean into light layers, easy fabrics, and clothes that carry you comfortably from afternoon to evening, especially if you’re spending the day wandering somewhere like the Indiana State Fair. We like to be a little dressed up, even in here, because the season is shifting and there’s something satisfying about clothes that nod to what’s ahead.

Dominick wears a broken-in Oxford shirt paired with his favorite jeans. These are easy-to-wear pieces that already feel familiar and lived-in. A classic repp tie and kiltie loafers complete the look. When work ends and the fair calls, it’s easy to adapt: the sportcoat comes off, sleeves get rolled up, and a hat slides on to complete the laid-back look. It’s a reminder that dressing well doesn’t have to be complicated. It’s about styles that transition with you.

Brandon wears a linen camp-collar shirt with breathable seersucker trousers, easy pieces for a warm day at the fair. A lightweight cotton sweater over the shoulders adds an extra layer for after sunset and keeps the look pulled together. Late-summer dressing at its most straightforward.

Noah wears a chore coat and chino combination in a similar fabric. We like to treat this as a casual take on a suit— slightly elevated while still robust enough to handle any mustard stains life might throw at you. Shown here with a white tee, it works just as well with an Oxford shirt or even a tie.


What makes late summer dressing so compelling is that it asks you to balance two things: warmth and the promise of cooler days ahead. It’s not quite fall, but it’s not the full heat of summer either.

This gives clothes a chance to pull double duty. Layers become essential. Look for pieces that you can shed or add as the day changes. Fabrics like linen, seersucker, and soft cotton knits shine because they breathe well and age gracefully. It’s an act of anticipation. It’s about taking familiar pieces and wearing them with intention, whether you’re wandering fairgrounds, heading to a cookout, or enjoying a quiet moment before fall. 

Ready to update your late-summer wardrobe? Explore these looks and more in our online store or visit us in person to see the full collection. Enjoy free local pickup or have your order shipped for just $6.99 anywhere in the country. Dressing well this season has never been easier.

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