Style Scenario: Fall Casual Date Night

What are you going to wear? Sometimes it’s good to look at a few suggestions and then add your own tweaks and ideas. That’s what these are for. It’s time to hit the town for a date night, but nothing too fancy. It is, after all, almost Halloween. Maybe, you’re scary in love. Maybe, that was a terrible joke. Either way, you’re looking to get out and enjoy the cool, crisp fall air with a more relaxed vibe. The key to this outfit is flexibility – it works for a laid back dinner, desert, and maybe even an impromptu trip to a haunted house. We’re going for a bit of a monochrome, super easy to put together look here. Nothing fancy, but still super sharp in its simplicity.

The Jacket: J.Crew Sussex Quilted Jacket- $148. This thing is a workhorse. I wear mine from early fall on into winter, and it’s held strong for five years now. Great texture with no sheen to the outer fabric, and copious amounts of warmth thanks to the insulated lining. Strong brassware that has developed a nice patina over time and works just like day one. The newer version has a zippered breast pocket not seen on the version I’m wearing in the photo above.

The Sweater: Banana Republic Italian Merino Crewneck in Black – $39.75 w/ BRFAMILY ($79.50). Wonderfully soft with a strong knit and a fit that is close, but not overly snug. Opting for black here, despite a navy-blue jacket. It works well for night time gallivanting and creating a subdued color palette that lets the material quality and textures take the lead.

The Pants: Banana Republic Rapid Movement Athletic Fit Jean in Grey – $81.99 ($118). Another item from BR, but for good reason. These recently won best in show from our athletic fit jean round-up, and the grey color works wonders to lighten up the outfit and provide a nice change of pace from the typical dark wash jean and earth tone chino. Yes, bright colors and bold patterns are in fashion right now, but a monochromatic sweater & jeans look like this is dead simple, and perhaps, even a bit sexy.

The Watch: Hamilton Automatic Khaki Field Black/Brown – $381.61. Keeping the pseudo-tactical machismo theme going strong, this legend from Hamilton is a great option if you’re a one-watch guy. It can be the first, and last, Swiss auto you ever buy. It excels in this type of scenario and stands out with the brand cache and exceptional quality for the price.

The Belt: Made in the USA Allen Edmonds Suede Belt – $49.97 ($98). Suede is a great texture to break out in the fall, and brown works here despite the black sweater (yes really, try it and you’ll see). It plays well with the shoes and watch strap, and we’ve already broken the myth of no navy and black together, so let’s keep being rebels (I know, DANGEROUS) and do black and brown while we’re at it.

The Socks: John’s Crazy Socks – Halloween – $9. Skipping the repetitive refrain of “merino wool socks are the best!” to get a little crazy and have some fun. A co-worker recently pointed me to John’s crazy socks after seeing my cyclin’ raccoon socks. John’s Crazy Socks specialize in wild designs with a purpose, as they’re a father-son run business benefiting the Special Olympics. Check out their story here, and grab some socks while you’re there.

The Shoes: Clarks Atticus Chukka Boot in Brown – $135. Chances are, your first chukka was a Clarks. Here, Clarks steps up a level with a more comfortable version with unique stitching detail and improved leather quality. Ships and returns for free via Nordstrom.

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.