Date Night & Smart Casual Outfits for Men

What does smart casual mean for men, and what should you wear on a date? Below are 37 complete outfits from the Happy Gentleman lookbook: linen shirts and trousers for summer, knitted polos, blazers, and tweed suits worn with a turtleneck. Each look lists every item, and every item can be bought separately.

How to dress smart casual

Top: a linen shirt, a knitted polo or T-shirt, or a turtleneck. No tie.
Trousers: tailored, pleated or linen trousers rather than jeans or joggers.
Shoes: clean suede or leather trainers, loafers, derbies or Chelsea boots.
Layer: add a blazer for a restaurant or a date night, or a leather jacket for going out.

Date night and party looks (23 looks)

Outfits for dinner, drinks, parties and evenings out.

Sophisticated Layers (look #404)

Spring date night look: sage cotton 2-piece suit. Open look #404 in the lookbook.

Tweed Heritage (look #497)

Autumn date night look: green tweed 3-piece suit. Open look #497 in the lookbook.

Dark Green Whisper — New Tie & Shoes (look #591)

Party and date night look: green double-breasted 2-piece suit with a green shirt. Open look #591 in the lookbook.

Navy Classic (look #646)

Autumn date night look: navy herringbone tweed 3-piece suit. Open look #646 in the lookbook.

Refined Everyday (look #851)

Summer date night look: white cotton blazer. Open look #851 in the lookbook.

Open Linen Shirt (look #869)

Summer date night look: black linen outfit. Open look #869 in the lookbook.

Tee & Trousers (look #870)

Summer date night look: black polyester outfit. Open look #870 in the lookbook.

Smart Layered Shirt (look #871)

Summer date night look: beige cotton blazer. Open look #871 in the lookbook.

All Black Summer Evening (look #876)

Summer date night look: black polyester outfit. Open look #876 in the lookbook.

Navy Polo Monk Strap (look #907)

Summer date night look: navy cotton outfit. Open look #907 in the lookbook.

Sage Cotton (look #977)

Summer date night look: sage cotton outfit. Open look #977 in the lookbook.

Black Linen (look #1015)

Summer date night look: black linen outfit. Open look #1015 in the lookbook.

Brown Linen (look #1017)

Summer date night look: brown linen outfit. Open look #1017 in the lookbook.

Tan Linen (look #1022)

Summer date night look: tan linen outfit. Open look #1022 in the lookbook.

Cream Polyester (look #1025)

Summer date night look: cream polyester outfit. Open look #1025 in the lookbook.

Sage Cotton (look #1026)

Summer date night look: sage cotton outfit. Open look #1026 in the lookbook.

Brown Cotton (look #1027)

Summer date night look: brown cotton outfit. Open look #1027 in the lookbook.

Beige Polyester (look #1028)

Summer date night look: beige polyester outfit. Open look #1028 in the lookbook.

Contemporary Formal (look #284)

Autumn party and date night look: brown polyester 3-piece suit. Open look #284 in the lookbook.

Evening Distinction — New Tie & Shoes (look #638)

Evening party and date night look: navy double-breasted 2-piece suit with a black shirt. Open look #638 in the lookbook.

Brown Linen Polo Date Night (look #891)

Summer date night look: brown linen outfit. Open look #891 in the lookbook.

Burgundy Linen Monk Strap (look #894)

Summer date night look: brown polyester outfit. Open look #894 in the lookbook.

Burgundy Linen (look #1031)

Summer date night look: burgundy linen outfit. Open look #1031 in the lookbook.

Smart casual and everyday looks (14 looks)

Relaxed summer outfits in linen and knitwear.

Brown Linen Tonal Casual (look #872)

Summer everyday look: brown linen outfit. Open look #872 in the lookbook.

Beige Linen Tonal Casual (look #873)

Summer everyday look: beige linen outfit. Open look #873 in the lookbook.

Beige and Brown Linen Casual (look #874)

Summer everyday look: beige linen outfit. Open look #874 in the lookbook.

Beige and Sage Linen Casual (look #877)

Summer everyday look: beige linen outfit. Open look #877 in the lookbook.

Colour Block Knit Casual (look #879)

Summer everyday look: white polyester outfit. Open look #879 in the lookbook.

Brown Knit Tee Casual (look #880)

Summer everyday look: brown polyester outfit. Open look #880 in the lookbook.

Navy Polo Black Linen Casual (look #888)

Summer everyday look: navy cotton outfit. Open look #888 in the lookbook.

Camel Linen Gurkha Casual (look #890)

Summer everyday look: tan linen outfit. Open look #890 in the lookbook.

Olive Linen (look #1018)

Summer everyday look: olive linen outfit. Open look #1018 in the lookbook.

Beige Linen (look #1020)

Summer everyday look: beige linen outfit. Open look #1020 in the lookbook.

Brown Linen (look #1021)

Summer everyday look: brown linen outfit. Open look #1021 in the lookbook.

Black Knit Polo Casual (look #1023)

Summer everyday look: black polyester outfit. Open look #1023 in the lookbook.

Orange Linen Summer Casual (look #1024)

Summer everyday look: linen outfit. Open look #1024 in the lookbook.

Tan Linen (look #1030)

Summer everyday look: tan linen outfit. Open look #1030 in the lookbook.

Frequently asked questions

What does smart casual mean for men?

A neat, put-together outfit without a full suit or tie: for example a linen or knitted shirt, tailored trousers and suede trainers or loafers, with an optional blazer.

What should a man wear on a first date?

Something one step smarter than everyday wear: a linen or knitted shirt, tailored trousers and clean leather shoes or loafers. For a smarter restaurant, add a blazer or wear a suit with a turtleneck.

What should I wear in summer to look smart but stay cool?

A linen shirt with linen or lightweight pleated trousers and suede trainers or loafers. Linen is breathable and looks relaxed but still put-together.

Can I wear trainers with a smart casual outfit?

Yes, as long as they are clean and minimal, such as leather or suede trainers in white, grey, brown or black.

Open these looks in the lookbook

Every look on this page opens in the Happy Gentleman lookbook, where you can see all photos and add the whole outfit to your cart.

Sophisticated Layers (look #404)
Tweed Heritage (look #497)
Dark Green Whisper — New Tie & Shoes (look #591)
Navy Classic (look #646)
Refined Everyday (look #851)
Open Linen Shirt (look #869)
Tee & Trousers (look #870)
Smart Layered Shirt (look #871)
All Black Summer Evening (look #876)
Navy Polo Monk Strap (look #907)
Sage Cotton (look #977)
Black Linen (look #1015)
Brown Linen (look #1017)
Tan Linen (look #1022)
Cream Polyester (look #1025)
Sage Cotton (look #1026)
Brown Cotton (look #1027)
Beige Polyester (look #1028)
Contemporary Formal (look #284)
Evening Distinction — New Tie & Shoes (look #638)
Brown Linen Polo Date Night (look #891)
Burgundy Linen Monk Strap (look #894)
Burgundy Linen (look #1031)
Brown Linen Tonal Casual (look #872)
Beige Linen Tonal Casual (look #873)
Beige and Brown Linen Casual (look #874)
Beige and Sage Linen Casual (look #877)
Colour Block Knit Casual (look #879)
Brown Knit Tee Casual (look #880)
Navy Polo Black Linen Casual (look #888)
Camel Linen Gurkha Casual (look #890)
Olive Linen (look #1018)
Beige Linen (look #1020)
Brown Linen (look #1021)
Black Knit Polo Casual (look #1023)
Orange Linen Summer Casual (look #1024)
Tan Linen (look #1030)

Delivery, returns and sizing

Free UK delivery on orders over £49 (Royal Mail Tracked 48, 2–3 working days), or next-day DPD Express for £4.90. Orders placed before 2:00 PM (UK time) are usually dispatched the same day.
30-day returns and free exchanges on UK orders (return postage is paid by the customer unless the item is faulty).
Jacket and trouser sizes can be chosen separately. See the Size Guide for UK, US and EU sizes.
We ship to the US, Canada, Australia, New Zealand, Ireland and most of Europe.

More outfit guides

Need help choosing an outfit or a size? Email hello@happygentleman.com or use live chat.