Now everyone has contributed, here are my answers. I hadn't thought of my own answers when I asked the questions so it has been an interesting procedure ... Do you want to look like you fit in with what you perceive 'your type of person' to be? ‘My type of person’ is a gay man in his sixties who works in further education, sings in a choir and works in an amateur way in theatre and indie movies. I put the ‘gay’ in there as a descriptor of me, but not of my fashion choices 99% of the time; I wear comfortable, fairly nondescript clothes that suit the worlds I work in – chinos, button-up shirts and trainers for work, the same for choir (we have a ‘uniform’ for performances) and, to be honest, the same for theatre work. I ‘fit in’ in the sense that I don’t stand out – I’m never the smartest or the scruffiest in the room and rarely wear anything particularly eye-catching. I’m an introvert and like comfort and like to look approachable and ‘ordinary’ – and that’s how I dress. The type of person I am is expressed by my clothes. Do you want to stand out from others who are 'your type of person'? 1% of the time I do like to ‘stand out’. I might be performing in a music and/or spoken word context, in which case I may wear something that’s a bit of a costume. I might be attending a performance I’ve worked on or a screening of an indie movie I’ve been on the team for, in which case I will want to look a bit special, but these aren’t posh events so ‘dressing up’ means wearing a nice shirt and jacket rather than a suit or anything too formal. If I feel I deserve to stand out (and with performance, I do!) I will wear something that marks me out a bit. But my ego tells me I want to be seen first, before anyone notices the clothes. I am the picture; the clothes are the frame. Do you want to look strong and dependable? I am 6 ft 3, which gives me a bit of authority without me having to project anything, but I am not sure I look ‘strong’. I’d like people to think I’m dependable but I am not sure my clothes signal that, necessarily.

@Canyon Rehbein That's a good start. One leg per trouser leg, got your shirt on the right way round, that kind of thing ...

Do you get those trousers professionally cleaned? I like pleats but find them impossible to iron - I have ruined pairs in the past. Your friend is spot on with the grey - Cary Grant in North by North West springs to mind.

@Brian McGuire I learned to always iron pleats through a cloth so they don't get shiny. I never seemed to be able to get them quite as good as when the trousers were new.

Stick to your natural colour. No chemicals, no expense.

@David Ginsberg Nature is more refined than any dye job.

You're allowed in, it's OK.

@Robert Woodhouse Blue is always reliable for me.