If you wear something often enough, do you start to suit it?

[YouWereRight]

I really don't think I look good in hats, but because I loathe the cold and sun I wear one most of the time.

Last night I was chatting with some friends and one commented on how well I pull off hats, when they look odd in them. I think this is because they're just used to seeing me in them, and not themselves.

Is this true? If I took to wearing yellow eyeliner, for example, would people eventually think it looks OK?

No.

These are two different things. One is whether you look good in something objectively. The other is whether people are used to seeing you like that so it becomes part of your look.

If you started wearing a sack cloth to work every day, it would be your look. Someone would eventually say "you pull off that sack really well you know." just because they have become conditioned to seeing you in a sack.

Not to say you don't look good in hats - you may well do!

I think you can sometimes feel more confident in something you were initially unsure of after a few wears, and then the confidence comes through and somehow it suits you better - you wear it rather than it wearing you.