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Wholefit is an independent outfit recommendation site. It isn't affiliated with or endorsed by the brands it shows, and you buy each piece on the site of the store that sells it. No store or brand pays us a commission yet; when one does, it won't decide what we recommend. * Prices include VAT, plus each store's delivery charges. Each piece is sold by the store named on its page.

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Discover Search

New looks, once a week

A few complete outfits picked from what's new. No account needed, unsubscribe any time.

Email address

Outfit ideas Brands Christmas party outfits What to wear with white trainers Women's date night outfits Men's work outfits Autumn outfits Winter outfits Streetwear outfits Minimalist outfits Women's workout outfits Men's smart casual outfits Outfits under £100 Outfits under £200

Wholefit is an independent outfit recommendation site. It isn't affiliated with or endorsed by the brands it shows, and you buy each piece on the site of the store that sells it. No store or brand pays us a commission yet; when one does, it won't decide what we recommend. * Prices include VAT, plus each store's delivery charges. Each piece is sold by the store named on its page.

About Privacy Policy Your Privacy Choices Terms of Use Affiliate Disclosure Brands & Copyright Accessibility Contact

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Men's Date Night Outfits: 50+ Head-to-Toe Looks · Wholefit

Outfits / Men's date night outfits

Men's date night outfits

Date night outfits that feel special without trying too hard, for dinner, drinks or a show. 57 complete looks, each with why it works.

By Ivan Kachur · Updated October 2026

For a date I'd skip the suit and go for good trousers, a knit or a proper shirt, and shoes that aren't trainers. Loafers do most of the work in these looks. Add a jacket if it's cold.

Ivan Kachur, Wholefit

Get looks picked for you · 1-minute quiz

With brown · 34 looks

Blue cardigan, brown jumper & cream trousers
£580*
For cool days, about 5–12°C · Date night · 4 pieces from £75*
Blue cardigan, brown jumper & brown trousers
£569*
For cool days, about 5–12°C · Date night · 4 pieces from £79*
Navy wool coat, beige shirt & navy trousers
£894*
For cold days, about −5 to 5°C · Date night · 4 pieces from £69*
Grey coat, beige shirt & navy trousers
£864*
For cool days, about 5–12°C · Date night · 5 pieces from £69*
Navy jacket, navy flannel & cream trousers
£680*
For cold days, about −5 to 5°C · Date night · 4 pieces from £130*
Navy jacket, jumper & navy trousers
£864*
For cool days, about 5–12°C · Date night · 5 pieces from £160*

With cream · 28 looks

Black shirt, cream trousers & penny loafers
£515*
For mild days, about 12–20°C · Date night · 3 pieces from £75*
Pink coat, cream jumper & trousers
£554*
For cold days, about −5 to 5°C · Date night · 5 pieces from £61*
Navy jumper, olive trousers & beige desert boots
£479*
For cool days, about 5–12°C · Date night · 4 pieces from £79*
Blue shirt, cream trousers & black shoes
£760*
For mild days, about 12–20°C · Date night · 3 pieces from £220*
Navy jumper, khaki trousers & beige shoes
£428*
For cool days, about 5–12°C · Date night · 3 pieces from £79*
Blue overshirt, cream polo & cream trousers
£1,510*
For mild days, about 12–20°C · Date night · 4 pieces from £345*

With navy · 31 looks

Navy blazer, jumper & navy trousers
£780*
For cool days, about 5–12°C · Date night · 4 pieces from £115*
Jacket, orange jumper & trousers
£554*
For cold days, about −5 to 5°C · Date night · 5 pieces from £77*
Green jumper, black trousers & navy suede boots
£515*
For cool days, about 5–12°C · Date night · 3 pieces from £135*
Navy shirt, navy trousers & white penny loafers
£790*
For mild days, about 12–20°C · Date night · 3 pieces from £170*
Navy shirt, navy trousers & white penny loafers
£765*
For mild days, about 12–20°C · Date night · 3 pieces from £170*
Brown jacket, red jumper & navy trousers
£1,280*
For cold days, about −5 to 5°C · Date night · 5 pieces from £123*

With black · 24 looks

Olive shirt, charcoal trousers & black penny loafers
£605*
For mild days, about 12–20°C · Date night · 3 pieces from £165*
Brown wool coat, blue polo & brown corduroy trousers
£3,180*
For cold days, about −5 to 5°C · Date night · 4 pieces from £595*
Blue barn jacket, grey jumper & cream trousers
£2,455*
For cool days, about 5–12°C · Date night · 4 pieces from £295*
Cream barn jacket, green shirt & black trousers
£2,305*
For mild days, about 12–20°C · Date night · 5 pieces from £275*
Cream polo, blue trousers & black suede boots
£1,015*
For mild days, about 12–20°C · Date night · 3 pieces from £325*
Cream jacket, blue polo & grey pleated trousers
£2,380*
For cool days, about 5–12°C · Date night · 4 pieces from £595*

All looks

Filters

Budget for the whole look

Style

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One checkoutEvery piece from the same store

57 looks

Filter by brand in search

Universal Works · £79

Universal Works · £59

Rothy's · £84

Universal Works · £50

Navy jumper, beige trousers & loafers

£272* · Pieces from £59*

For cool days, about 5–12°C · Date night · 4 pieces from £59*

Would you wear it?

Universal Works · £79

Universal Works · £69

Rothy's · £120

Universal Works · £32

Navy jumper, navy trousers & navy loafers

£300* · Pieces from £69*

For cool days, about 5–12°C · Date night · 4 pieces from £69*

Would you wear it?

Paul Smith · £127

Tommy Hilfiger · £72

Tommy Hilfiger · £123

Green shirt, khaki trousers & brown suede boots

£322* · Pieces from £72*

For cool days, about 5–12°C · Date night · 3 pieces from £72*

Would you wear it?

Wax London · £295

Wax London · £165

Wax London · £135

Tommy Hilfiger · £123

Black coat, blue jumper & grey trousers

£718* · Pieces from £123*

For cold days, about −5 to 5°C · Date night · 4 pieces from £123*

Would you wear it?

Universal Works · £330

Howlin · £185

Brown coat, jumper & navy trousers

£844* · Pieces from £160*

For cold days, about −5 to 5°C · Date night · 4 pieces from £160*

Howlin · £230

Black jacket, jumper & brown trousers

£733* · Pieces from £155*

For cold days, about −5 to 5°C · Date night · 4 pieces from £155*

Universal Works · £200

Universal Works · £230

Universal Works · £180

Navy jacket, jumper & cream trousers

£779* · Pieces from £169*

For cold days, about −5 to 5°C · Date night · 4 pieces from £169*

Universal Works · £270

Universal Works · £59

Universal Works · £180

Oliver Sweeney · £229

Cardigan, black polo & cream trousers

£738* · Pieces from £59*

For cool days, about 5–12°C · Date night · 4 pieces from £59*

Universal Works · £170

Universal Works · £65

Duke + Dexter · £250

Olive shirt, brown trousers & black penny loafers

£485* · Pieces from £65*

For mild days, about 12–20°C · Date night · 3 pieces from £65*

Universal Works · £155

Howlin · £185

Oliver Sweeney · £260

Brown jacket, jumper & brown trousers

£755* · Pieces from £155*

For cool days, about 5–12°C · Date night · 4 pieces from £155*

Universal Works · £189

Howlin · £185

Universal Works · £40

Navy jacket, jumper & brown trousers

£738* · Pieces from £155*

For cool days, about 5–12°C · Date night · 5 pieces from £155*

Universal Works · £135

Universal Works · £230

Universal Works · £180

Duke + Dexter · £270

Brown gilet, jumper & navy trousers

£815* · Pieces from £135*

For cool days, about 5–12°C · Date night · 4 pieces from £135*

Wax London · £146

Wax London · £125

Wax London · £125

Tommy Hilfiger · £150

Blue coat, navy jumper & navy trousers

£546* · Pieces from £125*

For cold days, about −5 to 5°C · Date night · 4 pieces from £125*

Universal Works · £180

Universal Works · £230

Universal Works · £180

Overshirt, navy jumper & navy trousers

£739* · Pieces from £149*

For cool days, about 5–12°C · Date night · 4 pieces from £149*

Universal Works · £170

Universal Works · £139

Rothy's · £120

Navy shirt, khaki linen trousers & navy loafers

£429* · Pieces from £120*

For warm days, about 20–30°C · Date night · 3 pieces from £120*

More outfit ideas

Date night outfits
Women's date night outfits
Men's everyday outfits
Men's smart casual outfits
Men's work outfits
Men's weekend outfits
Men's workout outfits
Men's outdoor outfits
Men's Christmas party outfits
Men's office Christmas party outfits
Men's Christmas outfits
Men's New Year's Eve outfits

Men's date night outfits at a glance

On top: Knitwear or shirts
Bottoms: Trousers or trousers
Layers: Jackets or coats
Shoes: Boots or loafers & lace-ups
Colours that work: Navy, cream, brown and black
A whole look: £546–£864, typically £738

How these men's date night outfits come together

Counted from 39 of these looks.

The pieces that come up most

On top: Knitwear or shirts
Bottoms: Trousers or trousers
Layers: Jackets or coats
Shoes: Boots or loafers & lace-ups

Colours that work

Navy, cream, brown and black come up most often across these looks, so they make an easy base to build on.

What a complete look costs

Most whole outfits here cost between £546 and £864; the typical one is £738. Swap any piece to change the total.

Brands in these looks

Most pieces come from Universal Works, Tommy Hilfiger, Duke + Dexter, Drake's and Howlin. Each look checks out on the stores' own sites, one store at a time.