With Valentine’s Day on our doorstep, searches for ‘men’s date outfits’ are on the rise. Whether you’ve got a restaurant booking, or a wine bar in for a casual night, here are 5 outfits to recreate.

Look 1

Seb Martens is the man to check out for everyday casual looks with an edge. This leather jacket and classic Oxford shirt combo is a masterclass in how to do it well, without looking like you’ve tried.

GET THE LOOK…

A black leather biker jacket with silver zips, two side pockets, one chest pocket, and a wide collar—perfect for men’s fashion or as part of men’s casual date night outfits. Displayed on a plain white background.
Leather Biker Jacket
The Kooples, £450 (was £750)
A light blue, long-sleeve button-up shirt with a front pocket and button-down collar, perfect for men's casual date night looks, laid flat against a white background.
Classic Oxford Shirt
A Day’s March, £100
A thin, silver chain necklace displayed against a plain, light-coloured background—an effortless accessory perfect for men’s casual date night outfits.
Perrie Slim Chain Necklace
AllSaints, £169
Leather Tassel Loafers
Charles Tyrwhitt Leather, £149

Look 2

Lean into classic Italian men’s style with this cool, crisp look. An outfit that’s good enough to woo on the streets of Milan… even if it is your usual date-night at the local pub.

GET THE LOOK…

A beige short-sleeve knitted polo shirt with a collar and three buttons, displayed flat against a white background—perfect for effortless Casual Date Night Looks.
Knitted Polo Shirt
M&S, £25
Wide-leg, pleated beige trousers with belt loops and a button fastening, perfect for casual date night looks, laid flat on a light grey background.
Pleated Trousers
Zara, £69.99
A man with light brown hair and a short beard wears a brown checked blazer over a dark green jumper and dark trousers—a perfect example of casual date night looks—while standing against a neutral textured background.
Saltiel Suit Jacket
Octobre Éditions X Lafayette, £270
A pair of dark brown leather loafers with a low heel, penny slot detail, and rubber soles—perfect for Casual Date Night Looks—are positioned side by side on a light grey background.
Camden Chestnut Loafers
Moss, £69.95

Look 3

Hit the high/low sweet spot with something cosy and casual up top. And more formal, pulled-together on the bottom. Think tactile wools like mohair, merino or cashmere, paired with a perfectly tailored trouser. Penny loafers add a bit of personality – the kind that might get you a second date.

GET THE LOOK…

Beige long-sleeve wool cardigan with black buttons down the front, ribbed cuffs, hem, and neckline—perfect for casual date night looks—displayed on a plain white background.
Crewneck Cardigan
Suit Supply, £199
A plain white sleeveless vest is laid flat against a light grey background. The vest has a round neckline and simple, seamless design with no visible logos or patterns—perfect for effortless Casual Date Night Looks.
Sleeveless Vest
M&S, £15
A pair of black, straight-leg dress trousers with belt loops and a front crease, laid flat on a white background—perfect for creating refined Casual Date Night Looks.
Wool-Blend Straight-Leg Trousers
Cos, £119
A pair of black and white leather loafers, with WALK LONDON inscribed inside. Shown from a top and side view on a white background, these classic penny loafers are perfect for effortless Casual Date Night Looks.
Torbole Saddle Loafers
Walk London, £63.92 (were £80)

Look 4

GET THE LOOK…

Inky denim and navy always feel smart, stylish and cool. This layered look is casual enough for drinks at the pub, but would also fly if you move on to dinner afterwards.

A black double-breasted blazer with four buttons, a notched lapel, long sleeves, and an elasticated waistband—perfect for Casual Date Night Looks. The blazer is displayed against a plain light grey background.
Double-Breasted Blazer
Karl Lagerfeld, £335
A pair of classic blue denim jeans with a straight-leg fit, five pockets, and button and zip fastening—perfect for casual date night looks—laid flat on a white background.
Cliff Straight Jeans
Arket, £85
A dark blue, long-sleeve, button-up cardigan with two front pockets, perfect for casual date night looks, displayed flat on a white background.
Jarrow Mohair Cardigan
A Day’s March, £150 (was £250)
Desert Nomad Boots
Clarks Originals, £99.99 (were £150)

Look 5

GET THE LOOK…

Chocolate brown is the key to this look. While all-black can feel a little try-hard, these softer hues make the look feel effortless and cool. Play with proportions by pairing this season’s favourite leather bomber with wide-leg tailored trousers. It’s a subtle nod to old-school romance.

A black leather jacket with a front zip, two angled front pockets, a pointed collar, and ribbed cuffs and hem—perfect for Casual Date Night Looks—displayed against a plain light grey background.
Leather Bomber Jacket
Zara X Aaron Levine, £289
A plain, short-sleeved, dark brown T-shirt is displayed on a white background—perfect for effortless Casual Date Night Looks.
Cotton T-Shirt
M&S, £18
Sean Chelsea Boot
Walk London, £48.64 (were £80)
Pleated Trousers
Butter Goods, £74 (were £105)
Fashion, Mens, Outfits, Valentine's Day

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