We'll be the first to admit that the Timberland brand doesn't make us think of dressy shoes -- similarly-named rappers wearing jeans and light tan work boots is more like it -- so we were pleasantly surprised by the Timberland Boot Company Counterpane Oxford ($225). Not overly fancy, the Counterpane features a distressed dark brown suede upper, a traditional leather sole, and old-school oxford style. Speaking of Timbaland, what the hell ever happened to Magoo?
Originally popular in the '40s and '50s, chukka boots are making a comeback, and these Frye Rodney Chukka Boots ($180) are a fine way to be part of the revival. The Rodney's slightly utilitarian design is bolstered by distressed leather uppers, contrast stitching, corded laces, and welted, textured Vibram soles for secure footing.
Originally made for the military in the 1960s, the Converse First String Chuck Taylor Ox ($TBA) is a premium take on the classic sneaker that's sure to be in demand this spring. The OX is based on the classic All-Star design, but sports unique upgrades like a vintage rubber license plate logo in the rear, a higher rubber rand, a chambray upper in black or midnight blue, contrast stitching, and an improved cushioning system for all-day comfort.
Prepare yourself for a casual summer with the SeaVees James Perse Linen Slip-On ($150). Although they sport a higher price tag than your average boat shoe, these SeaVees partially make up for it with a soft, premium linen canvas upper, suede heel patch, unique light blue rubber sole, and understated design that blends well with whatever you're wearing.
The made-in-the-USA L.L.Bean Waxed Canvas Maine Hunting Shoe ($139) is the perfect transition from snow to spring showers. Part of the new L.L.Bean Signature line coming later this year, only 100 pairs of these special edition boots are available today. Like the original 1912 Maine Hunting Shoe, they're hand-stitched in Maine and exude rugged northeast style.