While I’ll not profess to be an expert of any kind, I have a few thoughts about what consitutes a well dressed man:
Dress as if you care about yourself.Don’t expect anyone to care about you or take you seriously if you don’t appear capable of dressing yourself or taking care of yourself. Nothing screams lack of self-respect than letting yourself go on the basic stuff. Does your hair look ok? Are you shaved and clean? Are your clothes clean and undamaged? That’s a good starting point.
Up your game by moving to button-up shirts instead of sweatshirts and t-shirts. Dress your age. For a man of 40 that doesn’t mean dressing like a man of advanced age, but it also does mean not dressing like a teenager. No huge logos, acid-wash jeans or sports apparel. Observe how some clothes don’t even look good on teenage boys and consider how much worse they’ll look on an adult man.
Anything promoting a company has to go. There has never been a promotional piece of clothing that looked good. Unless you’re a F1 driver or a pro footballer wearing your team colours, you’re not earning money promoting anyone either. It just looks silly.
Brand name clothes are allowed a subtle logo, but no more than that (given how research has proven that brand-name recognition can work in your favour when meeting new people).
No pre-worn or pre-torn jeans allowed. If you’ve bought expensive raw denims and worn them in yourself, you’re ok. That’s giving the clothes character. Only up until the point where you have a hole in the knee though, then it’s just scruffy.
No trainers or sports shoes, unless you’re training. Simple rule, but broken all over. I don’t care if you’re wearing rare vintage sports shoes, you’re still not appropriate. Go for some solid shoes that will, if you take care of them, last a long time. A pair of Dr. Martens can be a good start at a reasonable price.
When it comes to having nice clothes, put in the effort to take care of them. They will cost a bit more, but will pay that back by lasting longer. Learn how to iron your shirts (once you start wearing them daily, you’re better off doing this yourself), polish and look after your shoes, hang up your clothes and so forth. Invest in some shoe trees and clothes hangers.
So, basically, don’t be a slob.
That would be my take on things, as a quick summary. Sounds a little on the boring side? Be tidy and neat and happiness will follow? Hardly, this is where it gets fun. There is a world of style and clothing out there, there is lots to discover. Hopefully I’ll be able to bring a few readers along with me.