| will - I think you're reading the wrong sort of things into clothes. As MrFluffs alludes to, clothing is more about you as a person, and certainly should not be thought of in a way such as "certain clothes work in a certain location".
Your clothes should enhance YOU.
There are three things you should be taking into account for every outfit you wear.
1) Your physical attributes. What size should you be wearing? What colours suit your complexion/hair colour/eye colour etc. etc?
2) Your personality. If you're a surfer-dude who is laid back to the point of being almost vertical, you might pull off the board short look. If you're a legal trainee you may look (and more importantly, feel) more comfortable in a suit or some smart-casual clothing. No hard and fast rules here, but you should wear things that you're comfortable in and this usually means wearing clothes that are true to yourself and your background.
3) Context. If you're going to a really posh big-city cocktail bar, don't go in ripped jeans and a tee shirt. If you're going to some grimy indie club with sweat dripping off the walls and sticky floors, don't go in your best suit. None of the clubs near me are really the sort you see in the films, where people go in wearing smart suits and suit around supping expensive liquor (certainly not the ones I go into anyway!), so fittingly, the smartest I ever go out is usually a dark pair of jeans and a nice button up. Very often I will be less smart than that, because that wouldn't fit in at the sort of club I go to.
It doesn't matter how much your clothes cost, where you got them from, or even what they look like. If you buy really expensive, really 'cool' clothes from some high end retailer, but they are the wrong colour and don't suit your complexion, you wear them to the wrong social occasion and look out of place, and you actually feel a bit uncomfortable in them because they're not really "you", then they're going to have the exact opposite effect of what you thought buying expensive clothes would have.
Alternatively, if you buy cheap clothes, but make sure they fit well, are good colours for you, are true to your personality and are appropriate for the context and setting you'll be wearing them in, then you'll look a load better than the bloke I described in the last paragraph.
Clothes don't make the man, but they certainly can break him if he looks bad and certainly can help him both in appearance and because his confidence soars when he looks the business.
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