Allen Edmonds cordovan chukka boots

One of the grand old men of American shoemaking has teamed up with a newly resurgent mall brand to create the fall’s first must-have shoes: Allen Edmonds and Club Monaco have launched a line of chukka boots, monk straps, loafers and brogues for which the phrase “investment purchase” was coined. (And it’s a wise one: Each shoe undergoes a 212-step construction process; we’ve worn a pair of AE’s Cronmoks for three seasons now.) Our favorites are the cordovan chukka (above) and the two styles below. Skip your next three cheap shoe purchases, swap them for a pair of these, wear them with a suit or jeans, and you’ll impress wherever you go. $365-$650. Available at Club Monaco stores and clubmonaco.com.

Allen Edmonds Club Monaco monk strap shoes
Allen Edmonds Mora Monk Strap, $365

Allen Edmonds Club Monaco wingtip shoes
Allen Edmonds MacNeil Wingtip, $365