Introduction

I will be the first to admit that this is something of a niche topic – we probably aren’t all rampant first daters and the chances of one coming around soon are probably nil to slim. But I have no doubt that there are some lucky buggers out there who aren’t completely devoid of tekkers* and can actually find someone to go on a date with them, without having to coerce them into it.

Whilst you might think that you’ve done all the hard work by finding yourself a willing partner, it has in fact, only just begun. Date preparation can be an utter minefield and you’ve only got one (possibly two, depending on how sorry the person feels for you) chances to get it right.

First you’ve got to decide on what you’re going to do. I can’t really help you here, but I can tell you that the traditional cinema date is not a good choice – tell someone you would like to take them out to a dark room, where you can sit in silence, not look at them for 3 hours and stuff your face with popcorn will probably result in a slap.

Secondly, you’re going to have to decide on your outfit. What I can do here is give you some inspiration, quantify your own ideas, or stop you looking like a total burke at that all important first meeting.

But at this point I would like to highlight how these articles can be read on a more personal level. It must always be remembered that they are nothing more than a guide and that the outfits they feature are open to interpretation. They can also be utilised in many situations, such as ‘how to look good when you first meet the parents’, or ‘how to look good at a family party’.

These are all situations in which the principles and stylistic ideas I discuss are applicable – you just need to think outside the box.

So how do you look good on a first date?

The Day Time Date
Outfit Inspiration

Men's Day Date Outfit Inspiration

Going for a wander? Having an extended coffee or even doing something more extravagant? There are any number of things you could end up doing if you choose to have a first date during the day. It could be a mix of many things or it could be one single, really rather romantic outing (maybe pushing her around an ice rink at Christmas whilst she screams bloody murder.)

Whatever you end up doing, I would suggest you keep your outfit practical. If you don’t quite know where your day will take you, then you have to be prepared for all eventualities; think rugged fabrics and stain friendly colours (no one likes to see a man in white trousers with grass stains). To have this base covered, I would opt for denim or dark chinos. Our old friend slim fit will of course be the perfect Casanova in the bushes helping you out along the way, and indigo or navy will give you the perfect mix of smart and casual – ensuring you can border that great and confusing divide with ease.

With a darker pair of trousers you are already well on the way to maximum versatility, so wear them with a pair of quality shoes (brogues, desert boots etc) or white trainers. On top you could stick to menswear staples like Oxford shirts and good knitwear or a tee and denim jacket combo.

I think the key with a day time date is to show off your styling consistency. If you can’t be stylish everyday then all you are doing is showing off your one good outfit; bad move. Besides, you are more than likely going to be in a more relaxed environment so going too smart is going to be the wrong choice. You want to remain comfortable and unrestricted in what you wear, able to respond to changes in weather or activity at the drop of a hat and most importantly, not be overdressed. Think versatility and adaptability.

Being confident in your clothes will make a huge difference to your demeanour and subsequently the date itself. Don’t over think your outfit or make it too complicated, you’ll look silly turning up for a walk along the seafront in your roll neck and double breasted blazer.

  • Oliver Spencer Grey Basket Knit Bloomsbury CardiganOliver Spencer Grey Basket Knit Bloomsbury Cardigan
  • Asos Oxford Shirt With OverdyeAsos Oxford Shirt With Overdye
  • A.p.c. Selvedge New Standard Straight Leg JeansA.p.c. Selvedge New Standard Straight Leg Jeans
  • A.p.c. Suede Derby ShoesA.p.c. Suede Derby Shoes
  • Asos Denim Jacket With Borg CollarAsos Denim Jacket With Borg Collar
  • Reiss Bless Basic Crew Neck T-shirtReiss Bless Basic Crew Neck T-shirt
  • Topman Navy Slim ChinosTopman Navy Slim Chinos
  • Clarks Originals Wolf Stone Suede Desert BootsClarks Originals Wolf Stone Suede Desert Boots
The Drinks Date
Outfit Inspiration

Men's Drink Date Outfit Inspiration

The drinks date is perhaps the most informal of all scenarios – a few hours on the wine will probably loosen both your tongues. Of course, just how informal the date is will depend on where you go (and this will subsequently depend on the girl and how fancy you want her to think you are), but you probably aren’t going to be attending the Savoy.

However, being an inherently evening based event, at an establishment in which you will be surrounded by other people, you might want to make more of an effort and make yourself stand out from the crowd a little bit more.

Following one simple mantra: ‘keep it simple, keep it clean’, you can ensure you aren’t overdressing, under dressing or just making yourself look silly. Direct your outfit to your venue and stick to the basics that will always produce great looks. A pair of tailored trousers are a fantastic way of adding some subtle individuality to an outfit, they are still a hugely under appreciated item and early adopters will be giving themselves a big boost.

If you want to show your fashion forward side, leave the under layer and just wear a v-neck jumper tucked into the trousers. A bold belt can be a great focal point for your outfit and a pair of classic white trainers will tie the whole lot together without looking too forced.

Along the fashion forward lines you could also try a bolder print shirt to generate that instant wow factor that will dazzle your date into submission. I’ve received numerous compliments on my bolder printed shirts simply because they stand out more and catch the eye. They also exude quiet confidence.

  • Reiss Jupiter Merino Wool V-neck JumperReiss Jupiter Merino Wool V-neck Jumper
  • Topman Grey Vento Tweed Skinny Suit TrousersTopman Grey Vento Tweed Skinny Suit Trousers
  • Reiss Windslow Suede Embossed BeltReiss Windslow Suede Embossed Belt
  • Converse All Star Ox PlimsollsConverse All Star Ox Plimsolls
  • Allsaints Daito ShirtAllsaints Daito Shirt
  • Shore Leave Grey ChinosShore Leave Grey Chinos
  • Topman Starboard Penny Boat ShoeTopman Starboard Penny Boat Shoe
  • Braun X Dieter Rams Bn0032 Stainless Steel WatchBraun X Dieter Rams Bn0032 Stainless Steel Watch
The Dinner Date
Outfit Inspiration

Men's Dinner Date Outfit Inspiration

I have heard that girls can sometimes be intimidated by guys that dress well. They want the security of knowing that they are by far and away the most stylish and fashionable part of the relationship, and they want a man that they can shape and mould into their perfect partner.

This is clearly poppycock and, quite frankly, who would want to go on a date with someone like that anyway? (In my experience, 80% of girls do not have a concept of what is and isn’t stylish anyway.) We men should be able to tout our styling talents whenever we should wish, but whilst this should form the basis for our everyday lives, there are times when we should exercise our need for restraint.

Again, this is a situation in which the venue will play a big role in your outfit – the more formal the restaurant, the more formal your outfit. A look that focuses on British heritage is a great way to cover most bases, from informal to just below true formal dress codes. Mixing textures is an easy way to add some flair to your outfit and show off your style without shouting about it, while a tie can be another way of drawing attention to your face and spark conversation (a key part of any date). Make use of Matt Allinson’s tie tying alternatives to add another level to the outfit.

You could also make use of one of your suits – dressing it down with more casual shoes, a colourful pocket square, no socks and a roll of the trouser hem.

  • Reiss Clinton Lightweight Patch Pkt BlazerReiss Clinton Lightweight Patch Pkt Blazer
  • Allsaints Corunna ShirtAllsaints Corunna Shirt
  • Richard James Check Woven-cashmere TieRichard James Check Woven-cashmere Tie
  • Nudie Jeans Thin Finn Organic Dry Twill Skinny JeansNudie Jeans Thin Finn Organic Dry Twill Skinny Jeans
  • Asos Slim Fit Suit In Blue Herringbone Italian FabricAsos Slim Fit Suit In Blue Herringbone Italian Fabric
  • Uniqlo Men Fine Cotton Slim Fit Long Sleeve Shirt+e1Uniqlo Men Fine Cotton Slim Fit Long Sleeve Shirt+e1
  • Richard James Camouflage-print Cotton Pocket SquareRichard James Camouflage-print Cotton Pocket Square
  • Topman Teak Suede Tassle LoafersTopman Teak Suede Tassle Loafers
Final Word

So there we have my suggestions of how to look good on a first date. By creating outfits that are simple, easy to wear and practical you make yourself feel more comfortable, more relaxed and better to be around as a person. Your date will go much smoother if you don’t spend the entire time worrying about how you look and you just relax into what you are wearing.

The confidence you gain from being appropriately dressed will be multiplied ten fold into your interaction with your lucky partner and hopefully your date will be a success.

Let me know what you think and offer up any useful dating tips for those devoid of tekkers in the comments below.

Will

[* For our American readers: Tekkers = Technique]