5 Top Style Tips for the Valentine’s Dating Novice

If you are a man who usually throws on the first item of clothing he finds, no matter the weather or occasion, then Valentine’s Day may be a bit of a sore point.

The pressure to look your best could cause stress and panic, taking the edge off what should be a fun romantic day/evening with someone you love.

But panic not! Luckily, you will probably already have all the ingredients for the perfect date night outfit, it is just a matter of getting all the elements right and knowing what to avoid.

Here are five tips to ensure that your date is left with hearts in their eyes, not rolling their eyes:


1. The Perfect Fit

Valentine’s Day is the perfect excuse to pull out all the stops when it comes to what to wear. The clear go-to for many men on such an occasion includes putting together your best formal shirt from Savile Row, sharp jacket and smart trousers. Initially this combination sounds flawless, the mistake, however, is often the fit.

An ill-fitting shirt will automatically make what should be an integral element of a smart outfit look more like a toddler has raided his dad’s wardrobe, hardly a look that is going to get hearts racing. Similarly, a shirt that is too tight may leave you exposing more than you intended to during dinner, instantaneously making the wrong impression.

If all your shirts are a little baggy or too tight, sleeves a little long and the collars too wide, it may be time to invest in a made to measure shirt. Tailored items can seem like a daunting purchase, but many retailers now offer inexpensive options that can even be ordered online.

Similarly, make sure the trousers you have chosen to wear for the date are a good fit, so not too loose or too tight. They need to be the right cut for your body shape, for example, those with a triangle body shape should opt for straight leg cuts over skinny fit to even out the upper and lower body, adding proportion to the entire silhouette.


2. Precise Attention to Detail

‘Attention to detail’ is more than just a cliché! Something as simple as making sure your shirt is well ironed before your date will make a massive difference to your whole look.

Other details to pay attention to are your socks and tie. Socks are a nightmare, sure – somehow one of every pair you have ever owned is in a parallel universe, only accessed through your washing machine. But for special occasions it is vital that you wear a matching pair. A sharp slim-fit suit, crisp shirt and shiny lace-up oxfords, can all be ruined in an instant if your date catches a glimpse of one Christmas 2005 sock and one sock that says ‘world’s greatest son’ peeking out between your trousers and shoes.

Similarly, a poorly tied tie, particularly one that’s too long or short, won’t give off the suave impression you may be striving for. Either watch tutorials to achieve that perfect knot or forgo the tie all together and opt for a cool casual open collar.


3. Those Extra Touches

If you are the type of guy who wears a shirt and tie to work, then Valentine’s may require you to pull out all the stops to make it look like you have made a special effort.

Why not wear a tie and pocket square in your date’s favourite colour? Opt for cufflinks for the evening. Make sure to put on an extra spritz of that aftershave; if the date goes well, every time you wear that aftershave it will evoke a sensory response and trigger the memory of a romantic night.

For something to make you utterly memorable (though not outfit related), bring a single red rose to dinner. Even if your date is not a flower person, they will be more than delighted to be handed the flower that is synonymous with love.


4. Leave the Slogan T-shirts for Another Time

Everyone loves a slogan t-shirt now and then, it makes for a fun talking point over a casual pint with friends. But just imagine sitting down at a nice restaurant and the first thing your date reads is, ‘Sorry I am late, I didn’t want to come’, or ‘Tonight’s the Night’. It hardly sets the mood, and if it is a first date, makes a terrible first impression. The scene with Spike in Notting Hill springs to mind.

Slogan and graphic t-shirts should just simply be avoided in dating settings, at least until your date’s type of humour has been established and you are in a casual setting such as a bowling alley.


5. Shoes are Important

It is very easy to just slip on any pair of shoes before making your way out of the door, however, a lot of people judge a person by their shoes. And as Forrest Gump’s ‘momma’ said “there’s an awful lot you could tell about a person by their shoes”.

In some settings baseball shoes, sneakers and skate shoes are acceptable if, and only if, they are in a good, clean condition. Many male celebrities opt for a clean white sneaker, but you would be hard pressed to find any happy to go about with muddy, grass stained ones. If this sounds like your everyday shoes, it is probably best you reach for that formal pair, such as oxfords, brogues or monk shoes for your date outfit.

This is particularly important if you are taking your date to the races – check the dress code first!

It doesn’t matter if this Valentine’s is your first, second or 500th date with that special someone. Make sure they actually feel special by looking your best.


We hope you enjoy your date and if you are stuck for ideas for where to go see Valentine’s Day Ideas for Racegoers.

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Do NOT follow this link or you will be banned from the site!

Racing News, What to Wear, Competitions, Features, Betting Tips and More

Join our mailing list to receive the latest news and updates from our team. We'll bring the news to you about once a month. We NEVER share your data.

You have Successfully Subscribed!

Scroll to Top