Dress to impress

Clothes maketh the man, or so they say (whoever “they” are). This was never a problem for me in my previous life. I had four types of clothes: work clothes (suits, shirts), wedding clothes (with a little work clothes crossover), daily clothes (jeans, t-shirts) and nice clothes (nicer jeans, nicer t-shirts).

The latter group was mostly the smallest; I rarely went places informally where I needed to dress to impress, and the few items of clothing I had did the job. Only now, that section has become the most important in my wardrobe. As First Dates has taught me, no-one is going to be attracted to someone who looks like they’ve wandered in after a day out at the football.

Add to this the fact that mostly I didn’t buy my own clothing in the past and you can see the dilemma I found myself in. My ex had a particularly strong fashion sense (the closest thing she ever got to a hobby probably) and would regularly present me with new shirts, new trousers and more, usually because that meant she could hide the fact that she had spent three times as much on herself at the same time.

The week after we split I genuinely found myself wandering a department store looking for clothing. I found the campest shop assistant I could and simply told him I needed to buy things. I didn’t know what things, but things. I even TRIED STUFF ON! Truly, my world was changing.

Now I’m the proud owner of an evolving wardrobe (the quality and coherence of which is up for much debate), but this is presenting new problems. As someone who has rarely thought about clothing so much, what do I wear on an informal first date?!

I’ve gotten over this sometimes by going straight to meet them from work. That gives me a ready-made excuse and entirely eliminates the need for me to make a decision. I often dress fairly sharply for work – suit and tie with matching pocket square (Tom Haverford would no doubt be proud). This can very easily be worn on a date over some cocktails or a light lunch.

Otherwise I’ve found myself debating between a shirt with sleeves rolled up or a t-shirt, between light coloured trousers or dark, between which jacket I wear on the way there. It’s exhausting. But at the same time, it’s forming part of my preparation. It’s giving me the chance to look at myself and remind myself that I need to present the best possible version of me on the off-chance we are in any way compatible.

I’ve been on very few dates. Fewer still have resulted in second dates (in fact, at time of writing only one has). At this stage, with such a small sample size I’m not blaming my clothing choices; I hope I never get that desperate!

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