Don't Blow it | What to Wear on a First Date

Hello gentlemen, some of you may have got wind that I'll be appearing on the The Dating Live Show in November. Over the years I've been guilty of being over meticulous when it comes to selecting outfits for dates. Ironing my pocket squares and bleaching the crepes of my outer soles with obsessive-fastidiousness. 

Having pride in your appearance is one thing, but shouldn't be done at the cost of sucking all the fun and frivolity out of fashion. 

 

1# What NOT to wear on a first date 

No gilets. I made that mistake some years ago. My primary focus was utility on this particular date. It was nippy, we had been over familiar on the texts which meant I could dress down. My date arrived looking incredibly exotic in a Burberry dress and sequin jacket. Immediately she remarked upon my gilet and scoffed. 

The date was terrible, partly because my confidence was blown before we had even reached the restaurant. 

TIP: Make the effort. This is an audition. You're not watching the footy down the pub with your mates. 

  

2# Make that change

That's right listen to immortal words of Michael Jackson. If you're going to a date straight from work then you must prepare before leaving the house. Don't crumple your date gear into a plastic bag along with your lunchtime bananas. Make the effort; it's the best way to make a first impression. 

TIP: There are plenty of clothes carriers out there to help you keep your clothes immaculate during travel. I would recommend the David Gandy designed Aerodrome travel carrier for Aspinal of London.

 

3# Don't put on a costume

You're going on a date, you're not opening a store on Savile Row and there won't be a swarm of paparazzi flocking in a rugby like scrum taking pictures of you both. My point is you don't need to wear the punisher for this one. (The punisher is the one outfit in your wardrobe you wear to stop traffic). Wear something you feel confident and comfortable in. 

TIP: Choose comfortable fabric and less constricting clothes. Don't opt for any figure hugging. There is nothing more off putting for a woman than having a button pop off and land with deft defying accuracy in her flat white or Aperol Spritz.

 

4# Smart Casual 

When I go on dates I tend to wear neutral or monochrome colours, fitted jeans, contrasting each garment but softly. Ultimately I want my outfit to be reasonably safe, no garish or bilious motifs or logos. I'm a huge proponent that you can't go far wrong with a crisp white shirt.  

Just please wear clean brogues or trainers. (Despite my self-effacing opener about bleaching the crepes of my trainers, I still dutifully clean them before leaving for a date). 

TIP: To coin a football analogy you just need to run this into the corner flag. You've done the hard work and got her on a date, don't risk going for broke on anything ostentatious. Simply obey a couple of rules; clean trainers, fitted clothes not spray on, no gambles. If you'd like to embellish the look at all accessorise a little with bands, bracelets, necklaces, certainly a watch. 

 

5# Envisage and give her something new

Dress your age. I've completely forgotten about that one. Remember you're 35 not 25, no need to rock the R2D2 tee shirt, unless you're taking her to a convention. Actually, screw that. Who cares if it's a convention, dress like you're auditioning for the role of future husband.

When you arrive on your first date you should also wear something that she hasn't seen in your online profile picture. She might see you in that outfit that you're wearing in a dozen or so Instagram posts and think you're wardrobe survives on shoestring budget. When you ask her to go halves on the coffee, no matter how 'new man' you want to come across, her suspicions will be confirmed. 

TIP: Not every date warrants a new trip to Reiss, but change the order up. Make sure there's a new combination that hasn't been snapped or seen before. If you're really on a shoestring budget ask a close friend if you can borrow 'that shirt' you like. 

  

6# Believe in yourself

You know my philosophy of never being in competition with yourself. This ideology has to be nailed down before you arrive on the date. 

You need to project the best version of yourself and your choice in wardrobe will say a lot more than the spoken word ever could.

Being comfortable and most importantly confident in the clothes you are wearing will breed confidence in other areas of your date, such as the chat and the flirty interactions.

Remember above all else, have fun. Remember to smile, like she said, 'You're never fully dressed without a smile'.  

TIP: Don't slouch; make sure your posture is not slovenly and hunched. Try and arrange the date in a venue you're familiar with to ease anxieties. Opt for comfort over style. Again, this is a date, not a lifestyle shoot for GQ.