Conversation Skills
For Men

How To Dress Smart Casual For A Date

July 26, 2019
▪ 5 mins read

Let's deal with the "What should I wear for my date" once and for all

If you have ever wondered what to wear on a date, smart casual is it.

You'll also notice it listed as a dress code on things like wedding invitations (which btw are great places to meet women) so I wanted you to get a clear guide on how to dress to sort-of impress.

To help with this I have roped in my friend and apersonal stylist for men Sarah at Sartorialab who is the expert on this! Over to Sarah...

Smart Casual covers a wide area of items - anything in between a suit and jeans and a t-shirt, so no wonder people find it confusing.

As a personal stylist for men, this is the area I get asked most about to help my clients with, so they hit the right balance between looking too formal or too casual. Here are my tips on how to dress smart casual for a date.


A blazer is a great starting point for how to dress smart casual for a date and is great for restaurants, theatres and smart bars. To avoid looking like you’ve worn half your suit, look for summer fabrics such as linen, cotton and seersucker or maybe a bolder check than you might wear for a suit. Blazers are usually slightly shorter than a suit jacket and details such as patch pockets will make it a little more casual too.

The more padded the shoulders the smarter it is, so scale this up or down according to when/where you're planning to go eg: an unlined cotton blazer with no padding in the shoulders would work well with a polo shirt and casual chinos for a lunch date in a pub, or a lined jacket with padding in the shoulders will go well with a smart shirt and formal wool trousers for cocktails in a smart hotel bar.

I find that many men go for a size too big, so do try on a size smaller when you’re out shopping too. Make sure it fits on the shoulders and have it nipped in at the waist if need be and make sure you have the cuffs taken up to the correct length to avoid looking like an overgrown schoolboy!

If a blazer is too smart, then opt for a bomber jacket, a field jacket or a cotton peacoat and unless it’s pouring with rain or you’re going sailing for your date, leave the anorak/windcheater at home!

Trousers and jeans

A pair of tailored slim fit cotton trousers or chinos, and a pair of neatly fitted, dark indigo jeans will work with a wide variety of jackets, shirts and knitwear, and form a great basis for your smart/casual dating wardrobe. Contrasting the colour of your trousers with your blazer to avoid looking like you have a slightly mismatched suit on.

There’s no upper age limit for jeans but if you’re older, I’d go for a smarter style. Dark indigo denim in a slim but not skinny cut is versatile enough to wear with a blazer and shirt for smarter occasions or a plain fitted t-shirt and trainers for a casual date, like a walk in the park. When buying jeans and trousers, make sure you look at your rearview in the mirror too to check how they fit on your bottom! Fit is one of the most important things to looking well-dressed so get trousers taken up so they have a small break on the leg, not puddles of fabric gathering around your ankles. This will smarten up your smart-casual for a date look!


The trick to getting a shirt that doesn’t look like you’re going to work and is more suitable for dating is to pay attention to the details. Choose softer collars or button-down collars or perhaps even a rounded collar or collarless style if you want something different. A subtle pattern such as a small spot, floral print or small check will work well or go for chambray cotton for a more casual style. A plain Oxford cotton button-down in white or pale blue is a classic and will go well with smarter trousers or chinos depending on the occasion. If you want to leave it untucked, make sure it’s a bit shorter so it’s not completely covering your bottom.


If you’re having dinner al fresco or going to an outdoor cinema for your date, then some knitwear may come in handy. Whichever style you choose - crew neck, v neck, long-sleeved polo shirt, half zip - go for a plain fine gauge one with minimal logos. This will be a touch smarter than a sweatshirt or hoodie or you could even go for a knitted blazer style which sits well in between formal and casual. Go for simple neutrals like navy or grey or try out colour like burgundy or dark green for a change, to look smart casual for a date.


Switching your shoes can change the whole look of your outfit. Brown is more casual than black and goes well with denim. You can make brogues or lace-ups look more casual if you go for a moulded rubber, chunky or coloured sole, and suede is a bit more summery than leather. You could also wear Chelsea or Chukka boots with jeans or casual trousers or monk-straps with smarter ones. Loafers are a good choice for more summery outfits and if you’re going on a casual date you could wear a pair of plain and simple leather trainers. Whatever shoes you choose, make sure they’re re-heeled, and polished if they’re leather, brushed if they’re suede, and clean if they’re trainers.


You can show a bit of personality with your choice of accessories. In summer when you may not have so many options of accessories to wear, a woven or striped canvas belt can add some interest to your outfit. Tone it with your shoes and the rest of your outfit. A flash of socks in a subtle stripe or spot helps to make your outfit look finished off and make sure they’re fresh and new looking. A pocket square can be a fun addition to a blazer. Women notice these small details and if you’re paying attention to yourself and how you dress, it feels like you’ll pay more attention to her too!

Sarah Gilfillan is founder of Sartoria Lab - a menswear style consultancy providing personal styling and shopping services for men. If you’d like some help putting together outfits for dating, please get in touch.

Now that you are confident in knowing what to wear, why not read my blog on 7 Hacks to Find Your Confidence?

Hayley Quinn smiling profile
About the author

Hayley Quinn is a leading dating and relationship coach, with 3 million views of her TEDx talk and 18 million YouTube views. She is spokesperson for Match, a columnist for Cosmopolitan, a regular contributor to international media, and has been published by Harper Collins (“The Last First Date”, 2022) and Simon & Schuster (“Do This, Not That: Dating”, 2023).

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