Porsche Design Chronograph 1 utility watch, $9,650 at Watches of Switzerland

Away Large checked luggage, $395/$276 at Amazon.com

Sunnywoo Nylon loop Apple Watch band, $7.99/$6.39 at Amazon.com

Heartboom Braided stretchy Apple Watch band, $9.99/$7.99 at Amazon.com

Butifacion Stretchy Apple Watch band (variety 10-pack), $9.99 at Amazon.com

Calvin Klein Boxer briefs (5-pack), $69.50/$27.98 at Amazon.com

Apple Watch Series 11, $360.05 at Amazon.com

Sendero No Luck hat, $32/$16 at Huckberry

UO Essential slim oval sunglasses, $15/$9.99 at Urban Outfitters

Club Unstructured Futura Wash cap, $26/$16.97 at Nike

Elemental gear tote, $199/$79 at Troubadour

Stone signet ring, $560 at Dries Van Noten

Bellerophon signet ring, $79.99 at MARCOZO

Triomphe signet ring, $480 at Celine

Oradina Duke signet bold ring, $715 at Nordstrom

Sterling silver oval signet ring, $952 at Deakin & Francis

Ledger signet ring, $195 at Miansai

Bold round signet ring, $178 at Mejuri

Flex boxer, $38 at KING

Linked leather belt, $98/$82.50 at Madewell

'D Duck' cotton twill cap, $115 at Drake's

Perfect Weekday tote (in olive green), $175 at Alex Mill

Mr P. Leather belt, $140/$84 at MR PORTER

Large Garment checked, $1,495/$1,195 at Tumi

Nubuck leather Weekend tote, $448/$268.80 at Banana Republic

Gap Tube socks (3-pack), $12.99/$7.79 at Old Navy

Athletic crew socks, $15.95/$12.99 at Gap

CNTSTSOCK colorblock socks, $9 at Los Angeles Apparel

Retro double-stripe socks (in burgundy), $15/$10 at American Trench

Radial Washed Helvetica crew socks, $15 at Stüssy

Rib socks, $16 at Kotn

Cotton ankle socks, $38 at Todd Snyder

Chunky Ragg half-calf socks, $22 at Bombas

Terry high socks, $25/$12 at On

Colorful socks, $4.90 at UNIQLO

Ribbed trouser socks (3-pack), $27 at Ralph Lauren

Colorblock socks, $35 at Alex Mill

Ribbed short socks, $18 at Iuman Intimissimi

Ribbed socks, $24.50 at J.Crew

Copper Corgi ribbed dress socks, $32 at Buck Mason

Embroidered Guinness Peak cap, $72 at Percival Menswear

Dual Tone crew socks, $24 at American Trench

Oval-buckle leather belt, $80 at Banana Republic

Seiko 5 Sports Automatic watch, $315/$252 at Amazon.com

Polo Ralph Lauren Striped twill tie, $125 at MR PORTER

Unimatic U4 Classic Military watch, $655 at Todd Snyder

Vaer S5 Tactical Field watch, $199 at Vaer Watches

SRPJ85 Field watch, $315 at Seiko