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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.

Pleats Please Issey Miyake Thicker Pleated Cocoon Pants Black at WDLT117, Toronto
Pleats Please Issey Miyake
Thicker Pleated Cocoon Pants Blk
$615Last one
WDLT117
Issey Miyake LUSTROUS WOOL Wrap Pants Black at WDLT117, Toronto
Issey Miyake
LUSTROUS WOOL Wrap Pants Blk
$1,144
WDLT117
RUOHAN Skara Jacket Dune at WDLT117, Toronto
RUOHAN
Skara Jacket Dune
$1,050
WDLT117
RUOHAN Umber Raas Coat at WDLT117, Toronto
RUOHAN
Umber Raas Coat
$2,279
WDLT117
Pleats Please Issey Miyake Basic Pleated Pullover Black at WDLT117, Toronto
Pleats Please Issey Miyake
Basic Pleated Pullover Blk
$308Last one
WDLT117
Nina Ricci Draped Satin Halterneck Sleeveless Blouse Black at WDLT117, Toronto
Nina Ricci
Draped Satin Halterneck Sleeveless Blouse Blk
$887Last one
WDLT117
MM6 Maison Margiela Pinstripe Wool Wide-leg Trousers Black at WDLT117, Toronto
MM6 Maison Margiela
Pinstripe Wool Wide-leg Trousers Blk
$720
WDLT117
Undercover Shadow Curve Trousers Black at WDLT117, Toronto
Undercover
Shadow Curve Trousers Blk
$1,201Last one
WDLT117
RUOHAN Loess Cocoon Jacket Beige at WDLT117, Toronto
RUOHAN
Loess Cocoon Jacket Beige
$2,316Last one
WDLT117
RUOHAN Mergui Coat Willow at WDLT117, Toronto
RUOHAN
Mergui Coat Willow
$1,042Last one
WDLT117
Nina Ricci Bomber Jacket Chocolate Brown at WDLT117, Toronto
Nina Ricci
Bomber Jacket Chocolate Brown
$1,664Last one
WDLT117
Litkovska Double Collar Poplin Shirt Blue at WDLT117, Toronto
Litkovska
Double Collar Poplin Shirt Blue
$720
WDLT117
Pleats Please Issey Miyake Thicker Pleated Flared Pants Beige at WDLT117, Toronto
Pleats Please Issey Miyake
Thicker Pleated Flared Pants Beige
$565
WDLT117
Y/Project Banana Slim Pants L.Blue at WDLT117, Toronto
Y/Project
Banana Slim Pants L.Blue
$289$774Last one
WDLT117
Ottolinger Liberated Double Jacket Green at WDLT117, Toronto
Ottolinger
Liberated Double Jacket Green
$1,028Last one
WDLT117
Coperni Technical Tailored Jacket Black at WDLT117, Toronto
Coperni
Technical Tailored Jacket Blk
$865Last one
WDLT117
Litkovska Blouse With Suiting Detail Grey at WDLT117, Toronto
Litkovska
Blouse With Suiting Detail Grey
$905Last one
WDLT117
Litkovska Shirt With Ribbed-Knit Sleeves Blue/Brown at WDLT117, Toronto
Litkovska
Shirt With Ribbed-Knit Sleeves Blue/Brown
$793
WDLT117
ERL Star Jacquard Light Wash Flared Denim at Utopia, Toronto
ERL
Star Jacquard Light Wash Flared Denim
$141Pre-owned
Utopia
Rick Owens Gray Tower Bolan Banana Trousers at Utopia, Toronto
Rick Owens
Gray Tower Bolan Banana Trousers
$459Pre-owned
Utopia
Denim Tears The Cotton Wreath Sweatpants Black at Utopia, Toronto
Denim Tears
The Cotton Wreath Sweatpants Black
$283
Utopia
Denim Tears The Cotton Wreath Sweatpants Grey at Utopia, Toronto
Denim Tears
The Cotton Wreath Sweatpants Grey
$283
Utopia
Rick Owens Edfu Bauhuas Cargo Pants Black at Utopia, Toronto
Rick Owens
Edfu Bauhuas Cargo Pants Black
$707Pre-owned
Utopia
Chrome Hearts Cross Patch Double Knee Carpenter Pants at Utopia, Toronto
Chrome Hearts
Cross Patch Double Knee Carpenter Pants
$14,130was $17,663
Utopia

Looks in this edit

Blue fold lines in Kiyosumi. An adult woman wears cream and blue Pleats Please layers, black cocoon trousers and pale blue Guidi shoes in a Tokyo courtyard.Blue fold lines in KiyosumiGolden hour at Diriyah. Flat lay of an umber RUOHAN coat, an ivory RUOHAN dress, beige Guidi loafers and a black Goyard bag.Golden hour at DiriyahA flight to Paris. Flat lay of a grey Issey Miyake dress, a black cardigan, black MM6 ballet flats and a yellow Louis Vuitton bag.A flight to ParisA lawn in the Hamptons. Flat lay of a pale blue Litkovska shirt, sand UJOH trousers, burgundy Guidi shoes and a black Goyard tote.A lawn in the HamptonsA Tuesday at the gallery. Flat lay of a graphite Litkovska blouse, graphite trousers, black Guidi derbies and a grey Goyard pouch.A Tuesday at the galleryArt Basel week in Miami Beach. Flat lay of a red Issey Miyake sweater, red trousers and a cream Celine crossbody bag.Art Basel week in Miami Beach

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.