Last Updated December, 2017.

As with cooking, so with style. The more you invest in quality ingredients, the better your final product. Flavoring and pairings give personality, context and place. A chambray shirt and cardigan with a wool overcoat versus a white shirt and blue blazer with a wool overcoat; oven-roasted chicken versus chicken parmesan.

The maxim of “buy better, buy less” applies here. Match good taste with smart purchasing, and the two will coalesce naturally over a period of years. The winter wardrobe may be more of an investment monetarily — with big-ticket outerwear pieces — but it is fundamentally rooted in functional layering pieces that provide warmth and protection from the elements. To lay the baseline, we present the 30 best staples that are definitely worth the investment.

Shirts

Easyday Oxford Shirt by Drake’s $165
Denim Western Shirt by Kapital $250
Checked Flannel Shirt by Remi Relief $250
Gab Checked Cotton Shirt by Officine Generale $270

Pants

Chinos by Outerknown $115
Jeans by The Worker’s Club $450

Outerwear

Denim Jacket by A.P.C. $290
Down Vest by Rocky Mountain Featherbed $610
Parka by Woolrich John Rich & Bros. $765
Double-Breasted Herringbone Overcoat by MR P. $865
Raincoat by Private White V.C. $1,135

Knits

Crew Neck Sweater by Inis Meáin $485
Chunky Sweater by Berluti $1,100
Cardigan by RRL $1,200

Basics

T-Shirt (2-Pack) by Velva Sheen $80
Henley by Faherty $100
Hoodie by Reigning Champ $155

Dress Clothes

White Shirt by Canali $240
Trousers by Thom Sweeney $520
Blue Blazer by Boglioli $1,250
Gray Suit by Prada $2,620

Footwear

Waterproof Boot by L.L. Bean $129
Lace-Up Boot by Red Wing Heritage $300
Minimal Leather Sneakers by Common Projects $510
Chelsea Boot by R.M. Williams $495
Oxford Shoes by John Lobb $1,340

Accessories

Casual Belt by KikaNY $135
Silk Tie by Drake’s $125
Wool Scarf by Anderson & Sheppard $190
Dress Belt by Crescent Belt Manufacturers $450
The 10 Best Hoodies for Men

In the world of casual outerwear, the hoodie embodies versatility. Read the Story

Note: Purchasing products through our links may earn us a portion of the sale, which supports our editorial team’s mission. Learn more here.