Fall Feelings: All the Layers of Men’s Fashion

Sharp Staff October 12, 2023

Indulge in the most empowering fits from the Fall/Winter 2023 collections — embrace the whims of seasonal style with tight-fitting balaclavas and sultry, indigo-coloured scarves. Headed out for the evening? Get dressed to the nines with the best in wool suiting and outerwear, complemented by top-tier accessories like diamond-set watches and leather bags. Fall temperatures bring freedom to the ‘fit, with autumn winds providing the perfect opportunity to add stylish layers and functional accessories to your everyday look.

Soft Landing

Upgrade your outerwear and brave the cold in an insulated puffer jacket engineered to withstand the winter elements.

Book for Men Fall Winter fashion photoshoot man in white winter jacket — *COAT ($1,595) AND BALACLAVA ($295) BY CANADA GOOSE; TURTLENECK ($60) BY SIMONS; PANTS ($1,575) BY HERMÈS.*

Mineral Assets

Nothing says glam quite like a diamond-set timepiece.

Book for Men Fall Winter fashion photoshoot three diamond watches on brown fabric — *[FROM LEFT TO RIGHT] MASTER COLLECTION ($4,000) BY LONGINES; SANTOS DE CARTIER ($17,500) BY CARTIER; CLASSIC FUSION TITANIUM DIAMONDS ($13,900) BY HUBLOT; TUXEDO ($3,095) BY BOSS.*

Well-Suited

During the season of celebration, turn up in a tuxedo that showcases the most elegant of eveningwear.

Book for Men Fall Winter fashion photoshoot pulling turtleneck over mouth — *TUXEDO ($3,095) AND TURTLENECK ($268) BY BOSS.*

Hat Trick

Relaxed yet contemporary, head-to-toe knitwear takes on a cool approach to business casual in elegant fabrics and accessories.

Book for Men Fall Winter fashion photoshoot man in fendi fedora — *SWEATER ($2,350) AND VEST ($5,995) BY BRUNELLO CUCINELLI; HAT ($920) BY FENDI.*

Suede Control

Add some texture to this season with a rich, long suede jacket layered over a classic shirt and tie.

Book for Men Fall Winter fashion photoshoot man in blue leather jacket and tie — *JACKET ($10,300), SHIRT ($1,420), AND TIE ($395) BY PRADA.*

Winter Wears

A classic tailored suit reinvented in wool makes for the perfect transitional approach to formal dressing.

Book for Men Fall Winter fashion photoshoot close up — *JACKET ($8,900) AND PANTS ($3,100) BY DIOR MEN.*

Après-Ski

From the slopes to the chalet, dress your best with sporty styles and dependable footwear.

Book for Men Fall Winter fashion photoshoot man squatting in striped sweater and track pants — *SWEATER ($1,190) AND PANTS ($910) BY MONCLER, AT HARRY ROSEN; TURTLENECK ($300) BY ATELIER MUNRO; BOOTS ($2,350) BY HERMÈS.*

Baggage Claim

Forego packing light with one of the season’s latest statement bags, where accessorizing takes on new shapes — with options from slouchy to structured.

Book for Men Fall Winter fashion photoshoot fendi bag

COAT ($1,295), VEST ($595), AND PANTS ($625) BY WANZE; SHIRT ($20) BY SIMONS; BAG ($7,600) BY FENDI.

BAG ($375) BY WANZE.

Book for Men Fall Winter fashion photoshoot leather and fleecey bag

BAG ($22,200) BY HERMÈS.

Book for Men Fall Winter fashion photoshoot prada bag

BAG ($5,000) BY PRADA.

Baggage Claim

1 of 4

COAT ($1,295), VEST ($595), AND PANTS ($625) BY WANZE; SHIRT ($20) BY SIMONS; BAG ($7,600) BY FENDI.

Baggage Claim

2 of 4

BAG ($375) BY WANZE.

Baggage Claim

3 of 4

BAG ($22,200) BY HERMÈS.

Baggage Claim

4 of 4

BAG ($5,000) BY PRADA.

Out of the Blue

Add new style staples to your wardrobe with an oversized, printed coat and bold graphic under-layers.

Book for Men Fall Winter fashion photoshoot model in flowing blue plaid — *JACKET AND SHIRT (PRICE UPON REQUEST) BY BURBERRY; KNOT RING (PRICE UPON REQUEST) BY TIFFANY & CO.; RING, TALENT’S OWN.*

Low Profile

A sleek, ultra-modern look calls for an ultra-thin watch.

[FROM LEFT TO RIGHT] L.U.C XP ($12,500) BY CHOPARD; JAZZMASTER THINLINE SPECIAL EDITION ($920) BY HAMILTON; SLIM D’HERMÈS ($9,720) AND SCARF (PRICE UPON REQUEST) BY HERMÈS.