An edit

Date Night Outfits for Men

Menswear for a night out, with silk shirts, bomber jackets, dark jeans, boots and sterling silver jewellery from independent boutiques.

Putting together date night outfits men reach for relies on balancing relaxed tailoring with tactile materials like silk, corduroy, and sterling silver. Dark indigo denim pairs naturally with fluid tops and deconstructed jackets in black or navy, keeping the silhouette sharp without feeling stiff.

Drôle de Monsieur was started by two self made designers from Dijon, and it mixes seventies prints with the nineties, when rap arrived in France. Mike Amiri made stage clothes for Los Angeles performers before he started Amiri, and denim is the core of the label. Song for the Mute is the Australian label of Lyna Ty and Melvin Tanaya, who have their fabrics made at mills in Italy, Japan and France.

Building the look starts with dark denim trousers, a fluid silk top, and an oversized jacket. Utopia in Toronto brings Amiri jeans, and Outlined in Toronto brings Ksubi jeans. Due West in Toronto adds Represent and Drôle de Monsieur tees and Emanuele Bicocchi silver pendants, while WDLT117 in Toronto brings Undercover and Song for the Mute jackets.

Undercover Prints Padded Jacket Gray Beige at WDLT117, Toronto
Undercover
Prints Padded Jacket Gray Beige
$2,055Last one
WDLT117
Undercover All-over Flower Print Blouson Black at WDLT117, Toronto
Undercover
All-over Flower Print Blouson Blk
$1,578
WDLT117
AMIRI Shotgun Jeans Deep Classic at Utopia, Toronto
Amiri
Shotgun Jeans Deep Classic
$530
Utopia
Amiri MX1 Shotgun Distressed Jeans Dark Indigo at Utopia, Toronto
Amiri
MX1 Shotgun Distressed Jeans Dark Indigo
$424Lightly used
Utopia
Homme Plisse Issey Miyake Quarter Zip Pleated LS Top Dusty Grey at WDLT117, Toronto
Homme Plisse Issey Miyake
Quarter Zip Pleated LS Top Dusty Grey
$561
WDLT117
Rhude Racing Crest Tee - White at Due West, Toronto
Rhude
Racing Crest Tee - White
$169$244Last one
Due West
Song for the Mute School Portrait Coach Bomber Camel at WDLT117, Toronto
Song for the Mute
School Portrait Coach Bomber Camel
$1,082Last one
WDLT117
Song for the Mute "Yawning Kid" Shirt Jacket Petrol Fade Out at WDLT117, Toronto
Song for the Mute
"Yawning Kid" Shirt Jacket Petrol Fade Out
$865Last one
WDLT117
Amiri Boucle Thrash Jean Antique Indigo at Utopia, Toronto
Amiri
Boucle Thrash Jean Antique Indigo
$707
Utopia
Amiri All Over Repair Jeans Clay Indigo at Utopia, Toronto
Amiri
All Over Repair Jeans Clay Indigo
$424
Utopia
Drôle de Monsieur Slogan Tee - White at Due West, Toronto
Drôle de Monsieur
Slogan Tee - White
$148
Due West
Drôle de Monsieur Slogan Tee - Navy at Due West, Toronto
Drôle de Monsieur
Slogan Tee - Navy
$148Last one
Due West
Les Deux Emmanuel Knit Polo - Green at Due West, Toronto
Les Deux
Emmanuel Knit Polo - Green
$77$112
Due West
Walk in Paris Timeless Burgundy T-Shirt - Burgundy at Due West, Toronto
Walk in Paris
Timeless Burgundy T-Shirt - Burgundy
$56$102
Due West
Drôle de Monsieur La Veste Jean Délavée Denim Jacket - Light Blue at Due West, Toronto
Drôle de Monsieur
La Veste Jean Délavée Denim Jacket - Light Blue
$329$442Last one
Due West
COOR Neff Cotton Denim Jacket - Indigo at Due West, Toronto
COOR
Neff Cotton Denim Jacket - Indigo
$166$314Last one
Due West
Ksubi Zoom Halen SS Tee - Natural at Due West, Toronto
Ksubi
Zoom Halen SS Tee - Natural
$148Last one
Due West
Walk in Paris Timeless Tee - Beige at Due West, Toronto
Walk in Paris
Timeless Tee - Beige
$81$95
Due West
Ksubi Van Winkle Baggy Cargo Light Indigo Washed Jeans at Outlined, Etobicoke
Ksubi
Van Winkle Baggy Cargo Light Indigo Washed Jeans
$159$212
Outlined
Ksubi Van Winkle Dark Indigo Washed Jeans at Outlined, Etobicoke
Ksubi
Van Winkle Dark Indigo Washed Jeans
$159$212
Outlined
Walk in Paris Timeless Tee - Brown at Due West, Toronto
Walk in Paris
Timeless Tee - Brown
$67$95
Due West
Les Deux Wild Flower Tee - Pink at Due West, Toronto
Les Deux
Wild Flower Tee - Pink
$53$70
Due West
Amiri Columns Of Duality Fringe Shirt Black at Utopia, Toronto
Amiri
Columns Of Duality Fringe Shirt Black
$495
Utopia
Amiri Bleach Bandana Plaid L/S Black at Utopia, Toronto
Amiri
Bleach Bandana Plaid L/S Black
$353
Utopia

Looks in this edit

Common questions

What core pieces work best for evening dressing?
A relaxed silk shirt worn under a lightweight jacket anchors the look alongside clean indigo denim or pleated trousers. Adding sterling silver jewellery gives a subtle finish without competing with the clothing textures.
How should colours and fabrics be paired together?
Stick to deep tones like navy, indigo, and black, using contrasting textures to create interest across simple silhouettes. Pairing matte corduroy with smooth silk keeps dark clothing visually distinct under evening lighting.
Which designers specialize in relaxed evening pieces?
Song for the Mute makes shirts, jackets and jeans from fabrics milled in Italy, Japan and France. Amiri, a Los Angeles label, puts denim at the core of what it makes, and Utopia brings its jeans here.