What NOT to wear on a date: 5 fashion faux pas to avoid

Avoid these mistakes to make a second date a little more likely

Knowing exactly what to wear on a date is a very difficult task. It’s something men have been trying to figure out for years. And to this day, many still don’t know.

You may never truly figure out to perfect combination of clothes. So instead of trying to solve this almost impossible task, let's list a few things you should definitely avoid!

First dates are a nerve-racking occasion, often meeting a complete stranger with an awkward series of back and forth questions and answers. The anticipation can leave some men a little bewildered and reaching for their everyday wear comforts. This mistake can leave a bad taste your date’s mouth before they get to know the real you.  

Here is a quick guide, complied by the Savile Row Company, on what to avoid on a first date and some suitable alternatives:

1. A Football Shirt 

If you’re a football fan, you probably feel at your best wearing your team’s colours. There’s something about team pride that brings out confidence in footie supporters. However, not only do these shirts scream casual lad’s afternoon/night down the local, they scream full on sports nut on a first date, raising instant red flags.

Although confidence is key on a first date, you should opt for a smart Savile Row Company shirt with the sleeves rolled up instead. More casual than a fully buttoned-up shirt, it’ll create a better impression than throwing on a top you would also happily wear to drink a yard of ale.

Partner a shirt with a pair of smart trousers or jeans (depending on the environment) and clean shoes for a laid back but presentable date wear look.

2. A Baseball Cap

A baseball cap, though a practical choice for sun protection, can make most well-groomed males look a little like Wayne Campbell, minus Garth. If your planned date involves walking about in the sun, then safety should come first.

In all other circumstances, wearing a baseball cap on a first date should be avoided.

Firstly, there are many that still consider wearing a hat indoors rude, so you will likely have to take it off anyway, exposing terrible hat hair.

Secondly, eye contact during a date is crucial. Not in a creepy stare kind of way, but more eye contact will help build a connection during conversation. 

Thirdly, if she leans towards you for that all-important first kiss, she is unlikely to be impressed coming into contact with the brim of your hat, face first. 

If you must wear a hat, choose one of the smarter options from T3's guide to the best hats for men 2019.

3. Flip-flops

Flip-flops are acceptable if your date is taking place on the beach, nobody enjoys sand in their shoes Otherwise, flip flops should be avoided at all costs.

“There's an awful lot you could tell about a person by their shoes.” – Forrest Gump’s Momma. 

Do you want your first impression to be your untrimmed toenails poking out the end of dirty flip-flops? Probably not. All this will say about you is either you don’t take pride in your appearance or you’re uncommitted to the date.

Some people are uncomfortable with feet full stop, so they probably shouldn’t make an appearance on the first date. Opt for clean sneakers, plimsolls or if you feel like stepping it up, choose some smart brogues or leather boots. 

4. Joggers 

There is a definite division of what’s classed as smart casual, and joggers definitely fall into the very casual bracket. They are comfortable, sure, but what kind of impression would turning up in joggers give? 

Most leave their joggers for DIY, those spring-cleaning days, couch potato Netflix binges or the occasional work out. Do paint, bleach, chocolate and sweat stains scream sex appeal?

If things do go well and moving in together is on the cards, whip the joggers out then. But until that point it’s important to put your best self forward. This doesn’t mean a three piece tux is your only option, even jeans are appropriate for a casual first date.

5. An Unkempt Beard

There is a huge movement for facial hair at the minute, giving guys the opportunity to step away from the razor, but this doesn’t mean you should become complacent with grooming. 

Beards can completely transform a man’s face, turning the baby faced into a rugged gent, they do require some maintenance though. A beard should be regularly trimmed to avoid it looking scraggly and unkempt. Use a scented beard oil to keep the hairs soft and glossy. 

If you are a man who has not been follically blessed it’s best to avoid attempting to sport a full beard, a patchy beard is no man’s best friend.

If you are a fan of the clean-shaven look, make sure you shave on the day and moisturise, giving that smooth finish.

Similarly, ensure your hair is well groomed before the big date. Clean and styled hair will prove that you look after yourself, which is an attractive feature in a date.

Remember, these are only guidelines, it is important to be yourself. But if that version of yourself wears joggers with a vest, flip-flops or a baseball cap it’s probably best to save that for a later date. You only get one chance to make a first impression, make sure it’s the right one.

And please remember to reach for that iron!

Spencer Hart
Style and Travel Editor

As the Style and Travel Editor at T3, Spencer covers everything from clothes to cars and watches to hotels. Everything that's cool, stylish, and interesting, basically. He's been a part of T3 for over seven years, and in that time covered every industry event known to man, from CES and MWC to the Geneva Motorshow and Baselworld. When he's driving up and down the country in search of the greatest driving roads, he can be found messing around on an electric scooter, playing with luxury watches, or testing the latest fragrances.