An edit
First Date Outfits
First date outfits from WDLT117, Utopia and Due West, each piece priced on 2 November 2026, from about CHF 139.
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, 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: After dark, before midnight, A hotel bar, late, A flight to Paris, A lawn in the Hamptons, A winter night in Doha, New Year's Eve on a Dubai rooftop, A Christmas party at the hotel bar, Christmas dinner in London
Rick Owens
Edfu Bauhaus Cargo Pants Black
CHF 590Pre-owned
Rick Owens
FW16 Mastodon Drawstring Cargo Pants Black
CHF 295Pre-owned
Chrome Hearts
Small Cross Pendant
CHF 1,770Pre-owned
Chrome Hearts
Small Cross Pendant
CHF 1,770Lightly used
MM6 Maison Margiela
Painted Denim Straight-leg Pants
CHF 581
MM6 Maison Margiela
5 Pockets Wide-leg Jeans Blue
CHF 596
Chrome Hearts
Double Cross Pendant with Bale
CHF 2,360
Chrome Hearts
Cemetery Ring
CHF 3,245
Avavav
Tim OS Shoulderless Hoodie With Lined Cut-out Application Beige
CHF 450
Avavav
Tim Shoulderless Hoodie AV-logo Black
CHF 318
Rick Owens
Cargobelas Cargo Pants Black
CHF 472Pre-owned
Rick Owens
Stefan Cargo Pant Heavy Faille Black
CHF 590
Tom Wood
Cushion Satin Ring (S)
CHF 315
Tom Wood
Open Cushion Ring
CHF 255
Maison Margiela
Painter Jeans Grey
CHF 295
Gallery Dept.
LA Painted Flare Carpenter Dark Brown
CHF 413Lightly used
Avavav
Trevor OS Shoulderless Slash Hoodie Aop Red
CHF 450
Song for the Mute
Raw Patch Pocket Hoodie
CHF 359CHF 476Last one
Gallery Dept.
Flare Sweatpants Cream
CHF 708
Gallery Dept.
Chino Flare Pants Black
CHF 295
Song for the Mute
Relaxed-fit Sweater Brown
CHF 476
Nike
X Stussy Fleece Crewneck Washed Black
CHF 148
Chrome Hearts
Cross Patch Double Knee Carpenter Pants
CHF 11,801CHF 14,752
Kapital
Souvenir Flare Track Pants Purple
CHF 148Lightly used
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.