Everything That Every Man Needs in His Winter Wardrobe

A close-up look at the details defining this season’s wardrobe.

Going Grey

Breathe some life into a classic grey suit by choosing a sturdy fabric, a standout plaid pattern, and playful button detailing.

JACKET ($3,620), SHIRT ($1,130), AND PANTS ($2,140) BY PRADA.

Tie One On

That classic woven belt you wore all summer gets a luxe leather upgrade.

LEFT TO RIGHT: ($690) BY BOTTEGA VENETA; ($630) BY BOTTEGA VENETA; ($200) BY JOOP!; ($1,620) BY TOM FORD.

Sole Cycle

The rusty fall palette of the ’70s is back in full force, and the best way to try it out is with a fresh pair of sneakers.

CLOCKWISE FROM TOP: ($725) BY SALVATORE FERRAGAMO; ($845) BY BRUNELLO CUCINELLI; ($565) BY MAISON MARGIELA; ($400) BY HOGAN.

Pink Collar

Yes, you too can wear pink, if you put your mind to it. Temper a bright piece like this with a muted (but coordinating) overcoat.

TURTLENECK ($2,150) BY BOSS; COAT ($5,475) BY ERMENEGILDO ZEGNA XXX.

Layer Cake

A monochromatic outfit almost never fails, especially if it’s in layers of supple brown.

SUIT ($1,295), SWEATER ($350), AND SHOES ($550) BY BOSS.

Sun Safety

Classic shapes subtly (or not-so-subtly) reimagined for the current moment.

1. ($530) BY CUTLER AND GROSS; 2. ($755) BY BOTTEGA VENETA, AT OPTICAL OUTLOOK; 3. ($650) BY BRIONI, AT OPTICAL OUTLOOK; 4. ($805) BY TOM FORD, AT OPTICAL OUTLOOK; 5. ($575) BY ALAIN MIKLI, AT OPTICAL OUTLOOK; 6. ($570) BY CUTLER AND GROSS; SWEATER ($125) BY COS.

Hold This Bag

The accessory of the season is a compact over-the-shoulder bag. Because AirPods and slim pants just don’t jive.

LEFT TO RIGHT: ($300) BY BOSS; ($1,690) BY PRADA; ($195) BY COACH; SWEATER ($350) BY BOSS; PANTS ($1,175) BY HERMES.

Shear Weight

The shearling jacket — a long-time winter staple — gets updated with a deep hit of colour.

JACKET ($3,360), TURTLENECK ($575), AND PANTS ($385) BY OFFICINE GÉNÉRALE; BOOTS ($1,550) BY HERMÈS.

A Case of Black and White

When it comes to a versatile timepiece, basic black is anything but.

1. BREITLING SUPEROCEAN AUTOMATIC 44 ($4,685); 2. NORQAIN FREEDOM 60 AUTO ($2,195); 3. MIDO MULTIFORT PATRIMONY ($995); 4. VACHERON CONSTANTIN PATRIMONY IN WHITE GOLD ($23,900); 5. RADO DIAMASTER AUTOMATIC GRANDE SECONDE ($3,470); 6. IWC PILOT’S WATCH AUTOMATIC 36 ($6,800); SWEATER ($650) BY WOOYOUNGMI, AT HUDSON’S BAY.

All Buttoned Up

Channel your inner Mr. Rogers by sporting a cardigan. Layer it in unusual ways (like over another sweater) to keep from feeling fusty.

CARDIGAN ($1,450) BY MARNI, AT HUDSON’S BAY; SWEATER ($990) BY FENDI.

Sweat It Out

A statement sweater isn’t just cozy — it’s a full-on fit unto itself.

SWEATER (PRICE UPON REQUEST), JEANS ($1,690), AND SNEAKERS ($1,480) BY LOUIS VUITTON.

Fall in Line

The striped power tie is making a major comeback. Put away your knit numbers (for now) and wear one of these with pride.

LEFT TO RIGHT: ($195) BY DRAKE’S; ($120) BY TIGER OF SWEDEN; ($340) BY ZEGNA; ($225) BY ZEGNA; ($150) BY PAUL SMITH.

Hot Hot Heat

Fall’s best new scents are deep, seductive, and ready for something heavy.

LEFT TO RIGHT: PRADA L’HOMME WATER SPLASH ($110); BOSS BOTTLED INFINITE ($110); YSL LA NUIT DE L’HOMME EAU DE PARFUM ($145); DIOR SAUVAGE EAU DE PARFUM ($215); ARMANI CODE ABSOLU ($155); PACO RABANNE PURE XS NIGHT ($105).

Arms Race

A military-inspired sweater is polished, tailored, and undeniably masculine. In other words: always a good plan.

SWEATER ($960) BY BOTTEGA VENETA; PANTS ($495) BY ELEVENTY.
PHOTOGRAPHY: RILEY STEWART (FUZE REPS)
STYLING: MATTHEW CHOW (P1M)
GROOMING: NATE (P1M)
PROPS: VANESSA SUPPA (JUDY INC)