An edit
First Date Outfits
First date outfits from WDLT117, Utopia and Due West, each piece priced on 2 November 2026, from about $72.
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.
First date outfits for men, piece by piece
- Jacket: Homme Plisse Issey Miyake Basic Pleated Jacket Black at WDLT117
- Top: Homme Plisse Issey Miyake MC V-Neck Tee Black at WDLT117
- Trousers: Homme Plisse Issey Miyake Straight-leg Pleated Trousers Black at WDLT117
- Shoes: Gucci Princetown Slipper Black Leather at Utopia
- Jewellery: Emanuele Bicocchi Fleury Cross Rose Medium Necklace - Gold at Due West
More looks in this edit: A Christmas party at the hotel bar, Christmas dinner in London, A wedding in December, An early flight out of Haneda, New Year's Eve in New York, October on the Canal Saint-Martin, Date night in black and chocolate, A holiday party in velour and pleats
Homme Plisse Issey Miyake
Edge Pants Black
$654
Homme Plisse Issey Miyake
Straight-leg Pleated Trousers Black
$526
Undercover
All-over Flower Print Blouson Black
$1,591
Song for the Mute
Daisy Worker Jacket Oat
$1,132
Homme Plisse Issey Miyake
Basic Pleated Straight Leg Pants Black
$482
Thom Browne
Charcoal Compact Waffle 4-Bar Sweatpants
$143Lightly used
Song for the Mute
School Portrait Coach Bomber Camel
$1,092Last one
Baracuta
Mens Wind Jacket G9 - Racing Green
$569
Undercover
Kasuri Pants Black
$781
Amiri
Baggy Trouser Jeans 70s Indigo Blue
$430
Baracuta
Mens Wind Jacket G9 - Marine
$498
Baracuta
Mens Wind Jacket G9 - Navy
$569
Amiri
M65 Denim Flared Camo Cargo Pants
$573
Amiri
Paint Splatter Black Flared Denim
$322Pre-owned
Homme Plisse Issey Miyake
Wool-like Pleated Pants Black
$639
Homme Plisse Issey Miyake
Wool-like Pleated Pants Grey
$639Last one
Song for the Mute
"Yawning Kid" Shirt Jacket Petrol Fade Out
$873Last one
Song for the Mute
"Daisy" Shirt Jacket Natural
$905
UJOH
Cropped Box Blouson Beige
$745
COOR
Pleated Washed Leather Jacket - Brown
$856
Baracuta
Mens Wind Jacket G9 - Dark Navy
$569
Baracuta
Mens Wind Jacket G9 - Natural
$569
Homme Plisse Issey Miyake
Wool-like Pleated Pants Chocolate
$566
Amiri
Denim Carpenter Jean Light Indigo
$430
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.