Guildsman Chambray Workshirt
Buy It Now at Land's End Canvas, $60

Allen Edmonds Stewart Plaintoe Oxford Shoes
Buy It Now at Land's End Canvas, $268

Elston 608 Slim Fit Chino
Buy It Now at Land's End Canvas, $60

Land's End might've been one of those mail-order catalogs your dad would get frumpy-looking gear from, but its Land's End Canvas line is definitely geared for style-minded guys. You can easily find it at the Land's End section at Sears, of all places. Carrying clothes like washed oxfords and red chambray shirts, you can dress them up with things like fair isle blazers and square-ended ties. Pants and jeans get a nice slim fit, and shoes are a menswear nerd's dream: collaborations with brands like Allen Edmonds and Oak Street Bootmakers, resulting in quality loafers and oxfords in dope colors like navy blue.