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An edit

First Date Outfits

Relaxed shirts, draped tops, pleated trousers, wide leg denim, and sterling silver jewellery for a first date at night.

A first date outfit pairs relaxed tailoring with tactile cloth so you feel at ease across a dinner table.

Pleated trousers create room through the leg while structured jackets give the shoulders a clean frame. Dark wool, crisp cotton, and fluid silk catch evening light without demanding attention, balanced by cool sterling silver jewelry. Song for the Mute, an Australian label, works with mills in Japan, Italy and France, and its designs include oversized shapes and frayed edges. UJOH was started by Mitsuru Nishizaki after years as a pattern maker, and Homme Plisse Issey Miyake pleats its pieces after they are sewn so they resist wrinkles.

Pair wide leg trousers with a light silk top and tailored outerwear for a composed silhouette. WDLT117 in Toronto brings most of this page, including Homme Plisse Issey Miyake pleated trousers and jackets. Utopia in Toronto adds Chrome Hearts silver rings and pendants, and Due West in Toronto adds Baracuta jackets.

Homme Plisse Issey Miyake Edge Pants Black at WDLT117, Toronto
Homme Plisse Issey Miyake
Edge Pants Blk
$648
WDLT117
Homme Plisse Issey Miyake Straight-leg Pleated Trousers Black at WDLT117, Toronto
Homme Plisse Issey Miyake
Straight-leg Pleated Trousers Blk
$521
WDLT117
Undercover All-over Flower Print Blouson Black at WDLT117, Toronto
Undercover
All-over Flower Print Blouson Blk
$1,578
WDLT117
Undercover Rigid Denim Jacket Indigo at WDLT117, Toronto
Undercover
Rigid Denim Jacket Indigo
$854Last one
WDLT117
Homme Plisse Issey Miyake Basic Pleated Straight Leg Pants Black at WDLT117, Toronto
Homme Plisse Issey Miyake
Basic Pleated Straight Leg Pants Blk
$478
WDLT117
Thom Browne Charcoal Compact Waffle 4-Bar Sweatpants at Utopia, Toronto
Thom Browne
Charcoal Compact Waffle 4-Bar Sweatpants
$141Lightly used
Utopia
Undercover Kasuri Jacket Black at WDLT117, Toronto
Undercover
Kasuri Jacket Blk
$1,701
WDLT117
Song for the Mute Daisy Worker Jacket Oat at WDLT117, Toronto
Song for the Mute
Daisy Worker Jacket Oat
$1,122
WDLT117
Homme Plisse Issey Miyake Wool-like Pleated Pants Black at WDLT117, Toronto
Homme Plisse Issey Miyake
Wool-like Pleated Pants Black
$634
WDLT117
Homme Plisse Issey Miyake Wool-like Pleated Pants Grey at WDLT117, Toronto
Homme Plisse Issey Miyake
Wool-like Pleated Pants Grey
$634Last one
WDLT117
Coor Pleated Washed Leather Jacket - Brown at Due West, Toronto
COOR
Pleated Washed Leather Jacket - Brown
$844
Due West
Coor Vegetable Swingtop Pleated Leather Jacket - Black at Due West, Toronto
COOR
Vegetable Swingtop Pleated Leather Jacket - Black
$774Last one
Due West
Baracuta Mens Wind Jacket G9 - Racing Green at Due West, Toronto
Baracuta
Mens Wind Jacket G9 - Racing Green
$562
Due West
Baracuta Mens Wind Jacket G9 - Marine at Due West, Toronto
Baracuta
Mens Wind Jacket G9 - Marine
$491
Due West
Undercover Kasuri Pants Black at WDLT117, Toronto
Undercover
Kasuri Pants Black
$775
WDLT117
Amiri Baggy Trouser Jeans 70s Indigo Blue at Utopia, Toronto
Amiri
Baggy Trouser Jeans 70s Indigo Blue
$424
Utopia
Baracuta Mens Wind Jacket G9 - Navy at Due West, Toronto
Baracuta
Mens Wind Jacket G9 - Navy
$562
Due West
Baracuta Mens Wind Jacket G9 - Dark Navy at Due West, Toronto
Baracuta
Mens Wind Jacket G9 - Dark Navy
$562
Due West
Amiri Boucle Patch Carpenter Jean Aged Black at Utopia, Toronto
Amiri
Boucle Patch Carpenter Jean Aged Black
$707
Utopia
Amiri M65 Denim Flared Camo Cargo Pants at Utopia, Toronto
Amiri
M65 Denim Flared Camo Cargo Pants
$565
Utopia
Song for the Mute TKL Denim Padded Jacket Khaki at WDLT117, Toronto
Song for the Mute
TKL Denim Padded Jacket Khaki
$651$1,127Last one
WDLT117
Song for the Mute Pleated Zip-up Jacket Sand at WDLT117, Toronto
Song for the Mute
Pleated Zip-up Jacket Sand
$651$1,198
WDLT117
Homme Plisse Issey Miyake Wool-like Pleated Pants Chocolate at WDLT117, Toronto
Homme Plisse Issey Miyake
Wool-like Pleated Pants Chocolate
$561
WDLT117
Amiri Paint Splatter Black Flared Denim at Utopia, Toronto
Amiri
Paint Splatter Black Flared Denim
$318Pre-owned
Utopia

Looks in this edit

An evening wedding in October. Flat lay of a black Undercover jacket, black trousers, a black Balenciaga shirt and black Louis Vuitton derbies.An evening wedding in OctoberNew Year's Eve in diamonds and pleats. Flat lay of a black Issey Miyake jacket, black trousers, a black UJOH sweater and black Louis Vuitton sneakers.New Year's Eve in diamonds and pleatsUndercover roses for a gallery night. Flat lay of a pink Undercover blouson, a black Masnada T-shirt and black Issey Miyake trousers.Undercover roses for a gallery nightAfter dark, before midnight. Flat lay of a black Masnada jacket, black trousers, a black Issey Miyake turtleneck and black Guidi derbies.After dark, before midnightA hotel bar, late. Flat lay of a beige MM6 jacket, a chocolate UJOH shirt, beige trousers, black Guidi boots and a Tom Wood ring.A hotel bar, lateA winter night in Doha. Flat lay of a brown Rhude jacket, an oatmeal Aime Leon Dore T-shirt, indigo Amiri jeans and white Jordan sneakers.A winter night in Doha

Common questions

What makes a good first date outfit?
Comfortable proportions and tactile fabrics keep the focus on conversation rather than fussy adjustments. Pleated trousers matched with an unstructured jacket strike the balance between considered dressing and personal ease.
Which fabrics work best for an evening date?
Natural fibers like wool, silk, and dry cotton drape naturally and breathe well indoors. Sterling silver accents add a sharp finish against darker evening cloths.
Which designers make relaxed tailoring for a date?
Homme Plisse Issey Miyake makes pleated jackets and trousers that resist wrinkles and dry quickly. UJOH, a Japanese label started by a former pattern maker, works with line and volume, and Song for the Mute cuts oversized pieces with frayed edges.