Stone-wash denim shirt, $375 at Drake's

Cotton tunic jacket, $1,315 at Drake's

Johnny collar polo, $65 at Abercrombie & Fitch

A&F Classic poplin shirt, $75 at Abercrombie & Fitch

100% merino wool crew cardigan, $110 at Abercrombie & Fitch

Holiday crew sweater, $85 at Abercrombie & Fitch

Classic Polished cropped tee, $25/$18.75 at Abercrombie & Fitch

Essential half-zip sweatshirt, $65 at Abercrombie & Fitch

Boucle Archive plaid crew, $80,200/$64,100 at Billy Reid

Herringbone Scout shirt, $48,000/$40,000 at Billy Reid

Flint and Tinder Vintage Soft Wash T-shirt, $108/$44 at Huckberry

Flint and Tinder Oxford Draftsman shirt, $98 at Huckberry

Flint and Tinder Surplus long-sleeve henley, $88 at Huckberry

100% Cotton relaxed quarter-zip sweater, $79.95/$50.40 at Gap

Shaker 100% cotton relaxed sweater, $59.95/$14.50 at Gap

Polo Ralph Lauren Fleece hoodie, $145 at Saks Fifth Avenue

India Ink Seafarer cotton quarter-zip, $228 at Buck Mason

Open Mongolian cashmere cardigan, $257/$99.90 at Quince

Wills Wool overshirt, $228 at Huckberry

Vintage thermal Surplus tee, $98 at Buck Mason

Shaggy alpaca fairisle sweater, $328 at Buck Mason

Natural shaggy alpaca saddle sweater, $268 at Buck Mason

Japanese denim Western shirt, $198 at Buck Mason

Quarter-zip sweater, $148/$103.60 at Madewell

Relwen Mock fleece, $168 at Huckberry

Pendleton Shawl Cowichan cardigan, $275 at Huckberry

Wills Merino-cashmere long-sleeve polo, $188 at Huckberry

YPB active classic tee, $45 at Abercrombie & Fitch

Knit utility shirt, $298 at Todd Snyder

Madewell x NYPL Vintage tee, $45 at Madewell

Vintage fit Polo-collar sweatshirt, $198 at Ralph Lauren

Vintage-inspired flannel shirt, $75 at Abercrombie & Fitch

Felton plaid shirt, $148 at Buck Mason

Devoe knit shirt, $118/$89.99 at Madewell

Dobby plaid shirt, $228/$90.50 at Billy Reid

Cutter overshirt, $178 at Taylor Stitch

Cropped plaid shirt, $79.90/$69.90 at ZARA

NN07 Deon checked mouliné woven shirt, $270 at MR PORTER

Kaptain Sunshine Checked shirt, $600 at MR PORTER

Relaxed-fit heavyweight overshirt, $180 at Banana Republic

Brushed camp shirt, $178 at Todd Snyder

Classic-fit plaid flannel workshirt, $150 at Ralph Lauren

Mr P. Western checked shirt, $210 at MR PORTER

Yarn dyed plaid overshirt, $250 at Aimé Leon Dore

Cotton plaid shirt, $28 at Noah

Sunwashed twill relaxed plaid shirt, $69.95/$34 at Gap

Wythe New York washed flannel workshirt, $188 at Huckberry

L.L.Bean Scotch plaid flannel shirt, $60 at Huckberry