How to dress?

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I have always wore Jeans and sneakers.

This summer when it was warm I took the plunge and started wearing shorts.

I have to wear a uniform in work.

I have come to the conclusion that I feel too old for Sneakers and Jeans.

Any opinions how should a 40 year old man dress?

Maybe I'm wrong, but I feel that in this day and age sneakers and jeans is something that's perfectly fine for 40 year olds to wear. They can even be some of the smarter looking types of sneakers and jeans if you like.

Gone are the days when our parents or grandparents' generations were expected to look stuffy and conventional and "age appropriate. I see much older men and women than 40 wearing comfortable sneakers and jeans at the weekend. Why not? They are comfortable and timeless items.

You could shop for some of the slightly more formal looking sneakers or shoes that have similarly soft and comfortable rubber soles and cotton uppers?

And jeans can be found that look very pressed, dark wash, and smart, rather than baggy and faded.

And there isn't actually anything that says they are strictly the province of the young. People of advanced age who run ranches or similar still wear jeans because they were the original tough wear for labor. Sneakers can also be sports shoes and all ages play tennis, etc. There's nothing to say these are teenager's clothes or anything.

If you really want to give up jeans though, maybe smart Dockers khakis? Those are still casual but look nice. Here are some.

Last edited by BirdInFlight on 02 Oct 2014, 4:29 pm, edited 1 time in total.

Psh. I'm 25, and I wear animal hats in public. I don't think you should worry about what you wear. I mean, I wore my Rainbow Dash wings and hat in public once I got them, and I could careless what people think. I dress however I want because I'm comfortable with the way I wear my clothes.

My mom dresses in clothes fit for a teenager, and she's close to her fifties. She's shorter than me (I'm 5'4, she's 5'2), and she doesn't care how she dresses either.

There's an older man I work with who I think always looks good (ok, I might have a little bit of a crush on him)
He wears casual cotton trousers in neutral shades, tan leather shoes (not the business kind - more casual in style) with ankle socks (I know, but it kind of suits him)
He wears smart cotton collared shirts with checks or other patterns worn loose, not tucked in. Sometimes he wears some of the surfie style brands like Billabong etc which look good also, but expensive.
He also wears cologne which smells really good - and I can't normally stand scents.

Go for something you've always wanted to wear. I saw some cool older guys last week. Their style was really slick and unlike anything around.

I used to wear trainers/sneakers for comfort a lot and wanted to switch to something smarter like desert boots, but none fit. These did and they're a middle ground between comfort and smart casual. I've worse them for interviews, even.

My current shoes:

^ Nice.

Reading all the replies thanks.

I'm not even a guy but those are nice shoes! They look comfortable.

Baggy brown t shirt and baggy jeans, can't go much wrong tbh.

They are and that's definitely something you've got to look for. But these were actually really cheap.

And what also sticks with me is a line from The Shawshank Redemption when he switches his prison shoes for the wardon's without anyone noticing because as Red says "I mean, seriously, how often do you really look at a mans shoes?"