The definitive guide to dressing for a date

 

Ah, the date. The excitement, the mystery, the drama, the pressure, the sweating, the trepidation… we know the feeling. In this most high pressure, high stakes of situations, wearing the right thing is critical but knowing what that right thing is? Not so easy. We’ve pulled together a little guide so whether it’s your first date or your umpteenth, at least one thing is for certain: you’ll look great. And some might say, that’s all that matters…

 

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The first date

It may be the result of a hasty swipe right or it may be the work of several months of planning, either way, the first date is nerve-racking and has a lot of potential for pitfalls. Outfit-wise, the way to think about it is, start with a great jacket. First impressions are the most important and your date will notice your outerwear first. A bomber jacket says easy cool and a heritage number speaks of sophistication and confidence. Pair with a tee that’s not skin-tight but not too baggy, and some great tapered jeans.

Boots are your date power player. They add a few extra inches and help you stand up tall (looking confident). At this point in proceedings, play it casual with a rugged, aged leather pair. Keep accessories minimal and groom and groom again. A spritz of cologne will do all the talking – even if you’ve run out of small talk.

 

 

 

First date

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The third date

By the third date chances are your rendezvous are becoming lengthier. When it’s a whole day date, you never know what’s going to happen. An art gallery trip may turn into a food market tour, which may turn into waltzing into some swanky hotel, which may turn into drinking till dawn. In such open-door scenarios, plan an outfit that covers all bases.

A checked shirt speaks of casual and suave at the same time. Layer a roll next underneath if it’s chilly, or wear over a t-shirt if you want to look more relaxed. A smart overcoat will work for a myriad of daytime shenanigans and will make sure you don’t get turned away if classy evening venues beckon. Smart jeans again follow this same logic and a comfy pair of chukka books will complete your ready-for-anything ensemble. 

 

Third date

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The fifth date

By the fifth date, it’s time for a surprise. Unexpected dinner prepared? Impromptu cocktail class arranged? The fifth date is when your outfit needs to say commitment-ready. You want to demonstrate your mature side, your dependable side, and the side that says ‘consider your boxes ticked’.  

Start with a great roll-neck. It’s the sophisticated king of knitwear that manages to look insanely cool and smartly cosy at the same time. Accessorise well. A great watch will show your credentials (suave but not too flashy). Swap your jeans for tapered chinos and your boots for classy, minimalist trainers. A chalky colour palette is your best friend but if want, add colour with your knitwear. Swooning, on your date’s side, will come part and parcel with this get-up we reckon. 

 

 

Fifth date

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The designated date night

Been together a while and got a specified date night in the diary? A long time spent together doesn’t need to equal less time spent getting the outfit right. Instead, when your partner knows your wardrobe in and out, it’s time to throw in a new piece. 

Take a modern approach to the suit by wearing the jacket and trousers with a clean-line knit or t-shirt. Wear some great loafers with a thin black sock and pull out your best watch. Put a bit of extra effort into grooming – you want them to notice. You don’t want to be the guy that just flurried straight from work in his unusual get-up. You want to be the guy that everyone in the restaurant notices and the guy that takes their partner by surprise. This will be you, my friend, we guarantee.

 

 

Date night

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