Boston leather and felt slide, $155/$100.75 at Birkenstock

Ossana V-neck sweater, $250/$150 at Velasca

Trench boot, $462/$346.50 at Oak Street Bootmakers

Pegasus 42 road running shoe, $145/$82.97 at Nike

FuelCell SuperComp trail sneaker, $219.99/$175.99 at New Balance

Made in USA 992 Core sneaker, $199.99 at New Balance

Palomo 1953 Baxter Camp Moc, $250 at Huckberry

Mayfare loafer, $150 at Dr. Martens

ADIZERO ADIOS Pro 5 shoe, $275 at adidas

Antelope textured Tuscan moc boot, $448 at Del Toro

New Balance 515 sneaker, $79.99/$39.99 at Amazon.com

Clarks Shacre II Run moccasin, $66.20 at Amazon.com

PUMA Club 5v5 sneaker, $83/$57.98 at Amazon.com

Cole Haan Newmark Grand chukka, $130.96 at Amazon.com

KEEN Pyrenees hiking boot, $180/$164.99 at Amazon.com

Clarks Bushacre 2 chukka boot, $110/$36.53 at Amazon.com

Timberland Motion Ledge shoe, $84.97 at Amazon.com

Reebok Shadoray tennis shoe, $54.95/$42.69 at Amazon.com

Jason Markk Protector Repel Spray, $36 at Amazon.com

Columbia Newton Ridge Plus II boot, $110/$77.89 at Amazon.com

Cole Haan Pinch penny loafer, $117.60/$59.99 at Amazon.com

Air Force 1 '07 WB shoe, $125/$89.97 at Nike

Tassel loafer, $99.90/$59.94 at ZARA

Waffle Racer sneaker, $95 at Nike

Paraboot Reims loafer, $635 at Todd Snyder

adidas BW Army sneaker, $90 at Farfetch

Made in U.S.A. 990v4 runner sneaker, $194.99 at New Balance

ACG LDV sneaker, $130 at Nike

Bryson suede Chelsea boot, $198 at Ralph Lauren

1876 Low hiker lace-up, $240 at G.H.Bass

Asics Gel-Transcend FJ hiking sneaker, $150 at Huckberry

FAST-R NITRO Elite 3 road running shoe, $300/$199.99 at PUMA

Moc-toe loafer, $238/$142.80 at Banana Republic

Italian suede sneaker, $158/$94.80 at Banana Republic

Rhodes Footwear Vibram Chelsea boot, $248/$211 at Huckberry

Paraboot Michael derby, $690 at Huckberry

Premium Authentic shoe, $90 at Vans

Vinny’s Lee Vale loafer, $349 at Huckberry

Autry Medalist low sneaker, $255 at Huckberry

Blacksmith boot, $329.99 at Red Wing

Birkenstock Amsterdam clog, $134.95 at Kith

Nike Zoom Vomero 5 sneaker, $140/$85 at Nordstrom

Crosby moc-toe chukka boot, $455 at Drake's

Larson Heritage Weejuns penny loafer, $225 at G.H.Bass

Star Master Sneaker, $99 at Huckberry

Yuketen Italian Hex Eye boat shoe, $807 at Havenshop

ACG Pegasus Trail GORE-TEX Waterproof Trail running shoe, $175 at Nike

Major Derby, $325 at Huckberry