Style Scenario: First Day it Feels Like Fall – Casual

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. We’re in a period of the year that I call “false fall.” Monday, it’s 67 degrees with a crisp breeze. Tuesday, it’s 86 and sunny. Wednesday, a humid 78 with all-day rain. But, the weather is cooling off, and there are token days where it feels like autumn before the complete season falls upon us. Here’s one way to look smart, even while dressed casually, as it cools off.

The Shirt: GAP Marled Henley in Olive Green Colorblock – $23.97 when 40% off ($39.95). This is my new favorite henley. Thicker than most, and cotton, so it isn’t super breathable. BUT, it provides a comforting, well-fitting (and flattering) thick feeling appropriate for those cozy vibes for fall. Oatmeal/Olive strikes a nice color contrast in fall-appropriate shades.

The Watch: Seiko 5 Automatic on Black Canvas – $75. $75 for this automatic watch from a historic brand? Tough to pass up. Canvas strap provides extra comfort for spontaneous fall adventures and all-day wear.

The Sunglasses: Sunski Andiamos Premium in Tortoise/Green – $89. Featured in the recent list of new arrivals for Fall, these Sunski premium shades are worth a try. A step-up from the usual Sunski options, so a step-up in price that bring them dangerously close to Warby Parker territory. But, still $10 cheaper and given that the “regular” Sunski sunglasses are phenomenal for the price, I have no reason to believe these won’t be proportionately excellent to the higher price.

The Belt: BR Tumbled Leather Belt in Dark Brown – $29.70 when 40% off ($49.50). More BR/Gap family inclusions in this scenario, but they do such a great job of executing the basics. This belt has a richer hue, and the darker buckle is unique.

The Jeans: Bonobos Premium Stretch Jeans in Resin Rinse – $111 w/ NEWJEANS ($148). A splurge, but these recently topped our Athletic fit jean round-up. Perfect taper, top-notch craftsmanship, and a fit that won’t quit. Spendy as all get out, but you’ll wear the heck out of them. And your pumpkin will look great in the process. Fingers crossed for a sale. UPDATE: There’s a sale! 25% off jeans through 9/22 w/ the code NEWJEANS

The Socks: Nordstrom Mid-Calf Merino Wool Socks in Navy – $12.50 (or 3 pair for $40). As noted in the intro, temperatures still fluctuate during false fall, so you’ll want a pair of socks to help your feet regulate temperature in the event you’re faced with an unexpected blast of heat during the day.

The Bag: Bleu de Chauffe British Millerain Lickwax Canvas in Black – $180 ($258). I do not know what lickwax is, and I do not recommend you read it as a verb, but this is one gorgeous bag.

The Shoes: Allen Edmonds Higgins Mill in Tumbled Leather Brown – $297 ($395). Another splurge, but $98 less than the brown chromexcel pair featured at the top of the post. These are my go-to fall and non-snowy winter boot. Exceptional comfort paired with outstanding leather quality leads to a reliable boot that can stand up to just about anything fall with throw it’s way. And, the quality is built to last. Think of it less as a splurge and more as investment.

About the Author: Jason P. is a Dappered devotee, having curated the majority of his wardrobe through the site. He is an enthusiast of wool sweaters, chino pants, and affordable automatic watches. In his free time, you can find him at his boxing gym or antiquing with his wife.