The first of three scenarios, depending on how dressed up a new job is. First day, first impressions matter.

Good looking, durable, functional stuff… that’s a bit of an investment but also on sale. Hooray winter clearance events!

Because you don’t have to dress as grey as the weather.

One of our annual traditions. What the big fella might be wearing on his busiest night of the year.

Gettin’ fuzzy with it.

Embracing the season by slowing down and taking it easy.

Here come the darker, richer colors and textures. Plus, each piece averages about $45.

Aging it down and keeping it casual while still avoiding slob territory. How do you do fellow kids???

Boots! Denim! Sportcoat! It’s a cornucopia of Dappered stereotypes!

Layered, but not heavily so, for when the air first turns to fall. No pumpkin spice necessary.

Damn it feels good to be a gangster.

It’s hot. Stay cool. Have a beverage.

It’s back! The best (arguably) league in the world returns this weekend.

Because sometimes you gotta go with shorts. Proving you can look put together even when it’s scorching outside.

Is it possible to assemble a head-to-toe, casual outfit for a 4th BBQ? Let’s find out.

Plus a poll on whether this is right on-trend, or trying way too hard.