Style Scenario: Feels Like Fall – Dressed Up


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What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. Football, finally seeing a break in the heat, and a few days that feel almost cold. It’s one of the best times of the year for dressing well. Here’s a dressed-up look to welcome that (very welcome) change in season.

2026 Feels like Fall Dressed UP

The Suit: Rowe & Tailor (Spier’s entry line) Medium Gray Wool Suit – $278. It’s hard to beat the versatility of a medium gray suit. To get some more use out of it, skip the tie and add an interesting eye catching accessory (like a pocket square), or a layer with some color like a rich brown v-neck sweater…

The Sweater: UNIQLO Extra Fine Merino Wool – $49.90. UNIQLO’s extra fine merino sweaters are thin but strong. Which is perfect for layering. And the color clearly says “fall,” without being plastic-trick-or-treat-pumpkin orange.

The Shirt: Banana Republic Wrinkle Resistant Dress Shirt in Slim or Standard Fit – $54 ($90). Great collars and wrinkle resistant 100% cotton.

The Watch: Timex Waterbury Classic Sub Second 39mm – $189. Mid sized case, quick release spring bars for easy swap outs to a black strap when you need one, and an interesting but still subtle dial with textures and layers.

The Socks: Darn Tough “The Standard” Mid-Calf Merino Socks – $27. Just enough cushioning and easy to wear dressed up or down. Mid calf for a little extra height for dressier occasions.

The Boots: LUCA Chelseas – $228. Sleek enough to wear with a suit, rugged enough to dress up some dark denim. Made in Portugal. Rubber & Leather combo sole.

The Belt: Banana Republic Classic Leather Dress Belt – $48 ($80). Classic indeed. Part of their 40% off F&F event.

Quad 575 Feels like Fall 2026 Dressed Up