within

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.

MM6 Maison Margiela Painted Denim Straight-leg Pants at WDLT117, Toronto
MM6 Maison Margiela
Painted Denim Straight-leg Pants
$703
WDLT117
MM6 Maison Margiela 5 Pockets Wide-leg Jeans Blue at WDLT117, Toronto
MM6 Maison Margiela
5 Pockets Wide-leg Jeans Blue
$721
WDLT117
Avavav Tim OS Shoulderless Hoodie With Lined Cut-out Application Beige at WDLT117, Toronto
Avavav
Tim OS Shoulderless Hoodie With Lined Cut-out Application Beige
$543
WDLT117
Avavav Tim Shoulderless Hoodie AV-logo Black at WDLT117, Toronto
Avavav
Tim Shoulderless Hoodie AV-logo Blk
$384
WDLT117
Chrome Hearts Small Cross Pendant at Utopia, Toronto
Chrome Hearts
Small Cross Pendant
$2,120Pre-owned
Utopia
Chrome Hearts Small Cross Pendant at Utopia, Toronto
Chrome Hearts
Small Cross Pendant
$2,120Lightly used
Utopia
Rick Owens Gray Tower Bolan Banana Trousers at Utopia, Toronto
Rick Owens
Gray Tower Bolan Banana Trousers
$459Pre-owned
Utopia
Rick Owens Edfu Bauhuas Cargo Pants Black at Utopia, Toronto
Rick Owens
Edfu Bauhuas Cargo Pants Black
$707Pre-owned
Utopia
Chrome Hearts Double Cross Pendant with Bale at Utopia, Toronto
Chrome Hearts
Double Cross Pendant with Bale
$2,826
Utopia
Chrome Hearts Cemetery Ring at Utopia, Toronto
Chrome Hearts
Cemetery Ring
$3,886
Utopia
Rick Owens FW16 Mastodon Drawstring Cargo Pants Black at Utopia, Toronto
Rick Owens
FW16 Mastodon Drawstring Cargo Pants Black
$353Pre-owned
Utopia
Rick Owens Cargobelas Cargo Pants Black at Utopia, Toronto
Rick Owens
Cargobelas Cargo Pants Black
$565Pre-owned
Utopia
Tom Wood Cushion Satin Ring (S) at WDLT117, Toronto
Tom Wood
Cushion Satin Ring (S)
$380
WDLT117
Tom Wood Open Cushion Ring at WDLT117, Toronto
Tom Wood
Open Cushion Ring
$308
WDLT117
Maison Margiela Painter Jeans Grey at Utopia, Toronto
Maison Margiela
Painter Jeans Grey
$353
Utopia
Gallery Dept. LA Painted Flare Carpenter Dark Brown at Utopia, Toronto
Gallery Dept.
LA Painted Flare Carpenter Dark Brown
$495Lightly used
Utopia
Avavav Trevor OS Shoulderless Slash Hoodie Aop Red at WDLT117, Toronto
Avavav
Trevor OS Shoulderless Slash Hoodie Aop Red
$543
WDLT117
Charles Jeffrey LOVERBOY Rabbit Ears Hoody Brown at WDLT117, Toronto
Charles Jeffrey LOVERBOY
Rabbit Ears Hoody Brown
$489
WDLT117
Gallery Dept. Flare Sweatpants Cream at Utopia, Toronto
Gallery Dept.
Flare Sweatpants Cream
$848
Utopia
Y/Project Multi Waistband Jeans Beige at WDLT117, Toronto
Y/Project
Multi Waistband Jeans Beige
$253$540Last one
WDLT117
Prada 2019 Double Match Split Bowling Shirt at Utopia, Toronto
Prada
2019 Double Match Split Bowling Shirt
$212Pre-owned
Utopia
Song for the Mute Relaxed-fit Sweater Brown at WDLT117, Toronto
Song for the Mute
Relaxed-fit Sweater Brown
$576
WDLT117
Chrome Hearts Cross Patch Double Knee Carpenter Pants at Utopia, Toronto
Chrome Hearts
Cross Patch Double Knee Carpenter Pants
$14,130was $17,663
Utopia
Chrome Hearts Pony/Patent/Leather Cross Patch Sweatpants Black at Utopia, Toronto
Chrome Hearts
Pony/Patent/Leather Cross Patch Sweatpants Black
$4,239Lightly used
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 nightBlue 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 KiyosumiAfter 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, late

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.