How to dress in smart/casual for a date

I was recently introduced to Hayley Quinn who's a professional dating coach.She runs live training programs, one to one coaching and a dating club, so if you're single and could do with a helping hand, then check out the options.

She mentioned that many of the guys need help with what to wear on dates, and so I wrote this blog post for her on How to dress in Smart Casual for a date.

The "smart/casual" term is used to cover such a wide area of items – anything in between a suit and jeans and a t-shirt, no wonder people find it confusing.

This is the area I get asked most about to help clients with, so they hit the right balance between looking too formal or too casual. So here are the tips I wrote for Hayley's clients on identifying what to look for and how to put things together:


Boglioli jacket - smart casual dressing for a date

A blazer is a great starting point for your smart/casual dating wardrobe 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 school boy!

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!

Sand slim fit unstructured cotton drill blazer - Boglioli at Mr Porter - £605


Drakes chambray shirt - how to dress smart casual for a date

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 a 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.

Blue cotton & linen chambray popover shirt - Drake's - £97.50

Trousers and jeans

Huit dark denim jeans - what shoud I wear on a smart casual date

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 rear view 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.

Slim selvedge jeans - Huit - £240


Burgundy John Smedley sweater - how should a man dress for a date

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 a colour like burgundy or dark green for change.

"Marcus" Bordeaux coloured crew neck merino sweater - John Smedley - £170


Paul Smith navy suede shoes - how to dress smart casual for a date

Switching your shoes can change the whole look of your outfit. Brown is more casual than black and goes really 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.

Navy suede "Andrew" Derby shoes - Paul Smith - £163


London Sock Company socks - ideas for smart casual dresssing for dating

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!

 "Shaken and Stirred" socks - The London Sock Company - £14

If you'd like some coaching around your dating life, then you can contact Hayley Quin here

Or if you'd like some help shopping for a smart casual dating wardrobe, then contact me here:

Contact Sarah

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