Let's lighten it up with a fashion question!

[KatZee]

And for the record: the examples of links you gave with what you wear is personally what I look for when I am out in the city. Laid back, comfortable, yet put together, and actually damn attractive.

[GemmaUK]

That video reminds me of Glastonbury and Reading festivals.

 

Well made good fitting khaki combats are a staple for that kind of thing - quick to dry and keep their shape better than jeans.

 

The shirt pics you posted are a little dull, maybe try a t-shirt with a shirt worn open over it.

 

I don't think a pair of Doc Marten boots can be beaten for casual or dressing up a bit in jeans. Those dress shoes look a bit like pull on trainers to me.

 

 

Good well fitted jeans with a belt and a good quality fitted white long sleeved shirt (one which the end of the shirt does not hang below your bum) plus the DMs and a nice watch - perfect for a night out!

A black shirt is equally good - get one of each (at least one of each).

Get a stainless steel watch for dressed up nights and a leather/black rubber strapped watch for chilled weekends.

Make sure your watch is up to date. You then don't need the rest of your kit to be 'trendy' as the watch will update the look.