Cotton oxford shirt: Gap, $35
Belt: Homemade, read our guide
Watch: Boldr, $259 (from my Watch Gang subscription)
Selvedge denim: Target, $39.99 (budget) / Naked & Famous, $140 (upgrade)
Boots: Red Wing Iron Ranger, $320
Weekend bag: S-zone, $40
Boot socks: Wolverine, $13 for 2
From a ‘template' perspective, this outfit has all of the makings of a dressy-casual outfit for a nice Mother's Day dinner, but it's the heftiness of the items that keep it casual. While you may be hesitant to wear a sweater and a collared shirt outside of a work situation, the ruggedness of the oxford cotton shirt, chunky knit sweater, heavy selvedge denim, and thick leather boots all work to make a comfortable, more casual outfit befitting the smart, successful guy you are.