Gerber Broadhead EDC Keychain, $11.99 at Amazon.com

Mono Stripe sock, $15 at American Trench

Rocky Mountain Featherbed Navy Wind tote, $95 at Drake's

Japanese Rib knit beanie, $30 at Huckberry

Tissot PR 100 Classic watch, $350 at Nordstrom

Wilson keyring, $15 at Craighill

Flint and Tinder Waxed canvas tote, $140 at Huckberry

Beams Plus Cashmere rib watch cap, $152 at Canoe Club

Cashmere beanie, $118 at Todd Snyder

Cashmere beanie, $34.90 at Quince

Cashmere beanie, $98 at Alex Mill

Rib-knit cashmere beanie, $178 at Ralph Lauren

Toteme Cashmere ribbed beanie, $260 at MR PORTER

Brunello Cucinelli Cashmere beanie, $620 at MR PORTER

Leather belt, $24.99/$9.99 at Gap Factory

Apple Watch SE 3, $249.99 at Target

Italian leather cashmere-lined gloves, $148 at Banana Republic

Moore & Giles Ward reversible tote, $290 at Huckberry

Bandolier Hailey crossbody leather phone case, $118 at Amazon.com

Perfect canvas pouch, $55 at Alex Mill

Shield bracelet, $280 at Burberry

Intrepid x Dimepiece ‘Blackout’ edition watch, $269 at Timex

Cashmere beanie, $118 at Todd Snyder

Leather briefcase, $2,350 at Bennett Winch

Leather belt, $88 at Madewell

Monk sunglasses, $248 at Buck Mason

El Dorado Western leather belt, $188 at Buck Mason

Stripe Loft-Lite merino beanie, $88 at Buck Mason

Italian leather carry-all tote, $598 at Buck Mason

Japanese Rib knit beanie, $30 at Huckberry

Bey-Berk Francis travel case, $135 at Huckberry

Timex Automatic 43mm Dive watch, $229 at Huckberry

Everyday Elevated crew socks (for 3-pack), $24/$19.20 at Nike

Calvi card holder, $460 at Hermes

American Optical Original pilot aviator glasses, $290 at Nordstrom

Barbour Nelson waterproof gloves, $100 at Nordstrom

Il Bisonte leather wash bag, $240 at Drake's

é Pebble grain leather belt, $95 at Le Alfré

Statement crew socks, $24 at American Trench

Marlin 1965 Reissue hand-wound watch, $259 at Timex

RB4435 frames, $89 at Ray-Ban

Active Premium Stripe crew socks, $24.99/$18.74 at New Balance

Practice merino crew socks, $24/$12 at American Trench

Heritage hardshell carry-on, $230/$183.99 at Herschel Supply Co.

Washed canvas tote, $58 at Noah

Osprey Arcane tote pack, $135/$70.73 at REI Co-op

Del Toro Western belt, $275/$148 at Del Toro Shoes

Favorite canvas tote, $59.95 at Gap