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Ah, Valentine's Day

Ah, the always unnerving 'what to wear on a date' scenario.  It's a tough time for a man; trying to blend what makes you feel comfortable with the expected dress code of the venue you're about to enter.  That is without even trying to factor in what they will be wearing.  And one particular day of the year becomes the cherry on top of what is already a sundae chock-full of confidence issues, low self-esteem and performance anxiety: good old St. Valentine's Day.  

So what do you need to start thinking about when it comes to dressing for a date on Valentine's Day?  Well, you want to make sure that whatever you wear, you feel comfortable.  This will ensure that you won't be focusing on other things such as how uncomfortable and awkward you feel, because this will translate in your body language.  More importantly, keep things simple.  You don't want to wearing anything too outlandish, outrageous and attention grabbing for two reasons: one, by toning things down and dressing in simple classic manner will bring your personality to the forefront - you're a man that's wearing the clothes, not the other way around.  Two, this special day happens to be all about him or her - so don't try and show them up, ok? Other than that, it's about dressing for the situation.  

Left to right: Reiss SS12, Aqua by Aqua SS12, Calibre SS12

Drinks and then a night out is probably the one scenario where you can really dress however you want, because it will depend heavily on where you're heading.  Saying that, why not take it up a notch for a change?  My go-to here would be a pair of skinny jeans and a white Oxford cloth shirt.  I'd probably top it off with a black leather jacket and some form of colourful socks.  But you could of course substitute to suit your own style.  If in doubt, stick to neutrals.  This is especially true of black and grey because they are always appropriate for evening events, communicate sophistication/elegance and can hide the inevitable strains that come from a night out brilliantly.

Left to right: Berluti AW12, Massimo Dutti '12, Banana Republic '12

The fancy date usually requires a reservation to be made at least a couple of months in advance.  This is normally at a restaurant, with the possibility of heading to a fancy bar for a few drinks after.  In this situation, I would suggest wearing a suit.  But do let me explain.  Don't dress it like a suit.  Skip the belt, the tie and loosen up a couple of buttons.  Opt for a suit with a bit of texture - such as grey tweed, khaki cotton or brown hopsack - in order to cement the off duty aesthetic.  Pair them with a simple striped shirt, a colourful pocket square and some burgundy or brown loafers.

Left to right: Allsaints AW12, Allsaints AW13, Calliope AW12

And of course we have the cinema date.  This one is a lot easier to dress for, as you'll spend a lot of the time in the dark anyway.  I would probably still wear a blazer, or at least a smart jacket, as it shows that you want to make the effort.  You don't have to go over the top with a formal version - why not opt for a more casual knitted style or a deconstructed cotton version?  Pair it with a neutral tee, a pair of casual chinos and some desert boots.  Of course, this is just a general suggestion for the majority so again substitute to mend your own style.  For those who want to dress down but dress well, try substituting the blazer for a shawl neck cardigan, classic trench or Harrington.  Oh and try not to be cheap on the popcorn and drinks!

Generally speaking, that's all there is to it.  Just be mindful of where you are going and the sort of expectations your lovely date has and you wont go wrong.  Then its just a matter of relying on your personality to get you through the evening.  Which is such a ball ache, right?  Why do they think we got into menswear in the first place?  So we could snare girls (or guys) with our fancy clothes and not have to worry about things like small talk and being interesting, of course.  What other reason could there be?  As for me, I will be spending another Valentine's Day alone (get the violins out already!), so if you want to join me watching Bridget Jones over and over again while sobbing into a wine glass, do let me know.  



Lucy Coogan said…
Love this.. I wish my Valentine was a man who dressed like one of these and knew when it was appropriate.. Rather than a book who won't cuddle me.. Haha.. Hope you had a good sob :P