Gold Rush Toddler Boys' "San Francisco" Zip Hoodie, $54.00

J.Crew: Boys' full-zip fleece hoodie, $29.50

Diesel Boy's Ombré Hooded Sweater, $99

Little Maven by Tori Spelling Boys' Zip Sweater, $64.00

J.Crew: Boys' wide-stripe sueded half-zip popover, $34.50

J.Crew: Boys' long-sleeve solid piqué polo, $29.50

Ralph Lauren Boys' Brown Novelty Polo, $50.00

J.Crew: Boys' long-sleeve rib-knit shawl-collar henley, $48.00

J.Crew: Boys' heavyweight lacrosse slub crewneck pullover, $48.00

Little Marc Jacobs Boy's Polo, $70

J.Crew: Boys' long-sleeve mountain dog slub tee, $22.50

J.Crew: Boys' long-sleeve Lake George slub tee, $26.50

J.Crew: kids' cashmere cable crewneck sweater, $125.00

J.Crew: Boys' wool herringbone vest, $69.50

J.Crew: Boys' Italian chino sportcoat, $148.00

J.Crew: Boys' two-button schoolboy blazer, $138.00

J.Crew: Boys' solid oxford shirt, $29.50

J.Crew: Boys' Secret Wash button-down in gingham, $39.50

J.Crew: Boys' Thomas Mason® fabric end-on-end shirt, $78.00

J.Crew: Boys' garment-dyed twill shirt, $39.50

J.Crew: Boys' vintage slim-fit jean in vintage blue wash, $58.00

J.Crew: Boys' Levi's® selvedge jean in worn rinse wash, $98.00

J.Crew: Boys' solid wool dress pant, $78.00

Diesel Boy's Khaki Cargo Pants, $69

J.Crew: Boys' wool peacoat, $178.00

J.Crew: Boys' quilted jacket, $65.00

J.Crew: Boys' wool toggle coat, $225.00

Diesel Boy's Quilted Puffer Vest, $75

D&G Juniors Boy's Fur-Trimmed Hooded Jacket,$345.00

Ralph Lauren Boy's "Ocean" Racing Jacket, $140

GAP: Cargo jacket, $39.50

Ralph Lauren Boys' "Lewis" Down Jacket, $140.00

UGG Australia Kid's Classic Boots, $90.00

Prada Hiking Boots, $240.00

Hunter Original Boots, $60.00

Ralph Lauren Plaid Snow Boots, $50.00

Converse Sneakers/Charcoal, $30.00

Prada Sport Sneakers, $195.00

Prada Striped Sneakers, $210.00

Diesel Toddler's & Little Boy's Sneakers, $80.00

J.Crew: Kids' Fjällräven® Kanken mini backpack, $60.00

J.Crew: Boys' vintage jeans belt, $28.00

Ralph Lauren Boy's Pima Cotton/Wool Jersey Scarf, $32.50

Ralph Lauren Boy's Pima Cotton/Wool Jersey Scarf, $27.50

GAP: Corduroy cap, $14.50

J.Crew: Boys' herringbone driving cap, $34.50

J.Crew: Boys' raceway baseball cap, $15.00

Janie and Jack: Herringbone Cap, $19.00

J.Crew: Boys' repp-stripe tie, $18.50

J.Crew: Boys' solid knit tie, $38.00

J.Crew: Boys' skull-and-crossbones tie, $22.50

J.Crew: Boys' navy-stripe knit bow tie, $24.50