it’s a date

So what makes the perfect date night outfit? What can make you exude the confidence you (or your man) need for that first date. Whether its with a special girl or guy, here are my top tips for date night confidence.

  1. Choose the right location/activity

There’s nothing worse than going on a boring first date. It is best to keep it simple for first dates, so you can really get a sense of the person you’re dating, but make sure the location/activity is somewhere that is interesting and has something you can do.

Some of the best dates I have ever been on, are those that have been at a completely random location. Ever been on a cocktail making date as a first date? Or bowling? Or even something like crazy golf? All these give another element to the date, so that even if you don’t have the instant chemistry you were hoping for, you can enjoy the time you are spending together.

  1. Choose an appropriate outfit starting from underwear

This is a key aspect to any first date (or second or third date). To ensure that your are as comfortable as possible starts by what you are wearing. This confidence will then show through in the date and the person you’re dating.

You don’t have to go full blown formal but make some form of effort. To me a guy who is well dressed, stylist but not overly formal can instantly increase their sex appeal.

Great first date rules for outfit choices are:

A) Wear comfortable fitting underwear. A great pair of boxers or briefs can make the world of difference to your confidence on a date. There is nothing worse than seeing a man wearing skinny jeans and having VPL. Guys, it’s not cool and it’s not clever!
Tommy John has the perfect solution for this, their Second Skin range (see right for the Tommy John Second Skin Platinum Trunk in Grotto colour). Not only does this range fit perfectly (ensuring there’s not nasty VPL) but also comes in some great confidence boosting colours, incase you want to match your undies with your outfit!
You can visit their site here, along with the rest of their products.

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B) Where a shirt. This can make or break a date for me. Not only does this make the guy look smarter, but it also makes your feel smarter and more prepared incase the date goes somewhere fancier. Great shirts include the Grandad Collar (for my previous Grandad Collar post click here), a plain oxford, or what is becoming more popular (especially in the urbanised areas of the UK) are Longline Shirts. ASOS, have great of Longline Shirts, perfect for every first date. The Nicce London Longline Diamond Shirt In Grandad Collar (right) combines the Grandad Collar and the longline aspect, and comes in at a reasonable £45.00.


C) Finally ensure that you’ve got great shoes. Whether its guys or girls, they’ll be checking out the kicks. Why not match the Grandad Collar with the super slick Black Nubuck Leather Brogue Chukka Boots (right) from River Island. As these aren’t patent leather they have a dull tone, but the smartness of any brogue, meaning that your date will clock cool but smart casual look straight away.

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  1. Be prepared.

This is where most guys fall down. Once you have the right location/activity and look, its easy to forget that the person you’re dating will be interested in getting to know you, without you droving on about work and the 24 problems you encounter on a daily basis (it’s difficult I know, but keep that for later).
Keep it simple, keep it positive and ask questions. There’s nothing worse than a guy who constantly talks about himself and isn’t interested in his date!

Keep it cool guys!

This post is in collaboration with Tommy John.


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