What To Wear On A Date

I’m confused. This may not surprise you much, since if you have read my previous posts some of the few things you will have learnt about me is that I know bugger-all about women, even less about fashion, and that I’m hopeless at dating.

And now I have been asked to write about all three of these tricky subjects by Miss X. I’m even more confused as to why – she seems to think that it might be interesting if I were to give you a primer on how to pull a chap like me. Is she trying to get rid of me? Surely this is not a good sign…

I asked her about this, and it seems that her boundless generosity to you, dear readers, extends to trying to reconcile some of the misunderstandings that often occur when men and women get together (it’s like Men Are From Mars, Women Are From Venus). Note that this might only be relevant if those men happen to be ones who misunderstand things quite as often as I do, and I am rather convinced that I am pretty much unique in that department. Probably not a great start then.

But here we go anyway with “What To Wear On A Date“. For those”Dos and Don’ts on the Date” keep an eye out for the next blog post.

1. Throw on something and don’t be late

Whilst you may spend hours agonising over your outfit, and trying on several in front of the mirror, this is a total waste of time. If you were to do this in the presence of a man he would say ‘That one looks nice.’ Then you would change into something else, and he would say ‘That one looks nice too.’ Just put on pretty much anything and get on with it because being late is not attractive. You can even turn up in tight jeans and, combined with a glimpse of whale tail, it’s super sexy in a slightly slutty but actually really hot sort of way.

2. To culottes or not to culottes?

As far as most gentlemen are concerned, the list of verboten clothes is extremely short. In fact it starts with shorts – no culottes or those abominations they called city shorts a few years ago. Women are only permitted to wear one kind of shorts and those are Daisy Dukes (which tend not to be appropriate on a date).

3. Say goodbye to shoulder pads, dungarees and silk scarfs

Apart from that, I think shoulder pads and dungarees pretty much round off the list. Oh, and I’m really not sure you should wear a silk scarf – it makes you look like an airline stewardess from the 1950s, or just that you are in your 50s yourself. There. See how easy it is? The date is about you, not your wardrobe, so relax.

4. It’s all about the heel

Again, don’t over-think it. Flip-flops, Crocs and ballet pumps are not sexy. Nor are those clumpy old spinster quarter-heels with buckles on the front. Apart from that trainers can even be quite acceptable if you’ve gone for a casual look, otherwise pretty much any pair of reasonably high heels is great.

Want to really seduce us? Go for something with strappy bits running up your legs, or the failsafe but very provocative allure of kinky boots. If you do need to walk to your date in some more comfortable shoes, just don’t spoil the effect by pulling the good pair out of your handbag and changing into them in front of us.

And there you have it. Simple, isn’t it? Just don’t try too hard to guess what you imagine we are going to like. Basically, we don’t want to think that you are going to over-complicate life, or that you lack self-confidence. We interpret that has high-maintenance and needy. All we want is a nice, independent and easy-going, fun girl with a sense of humour who doesn’t come across as being quite as unfathomable as most other women do. Someone a bit like Miss X, really.

Read more about Single in the City here.


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