Prep is good, whatever Jimbo had to say on the subject.
The whole bloody idea of 'Ivy League'/'prep'/'trad' if you will/casual American dressing is to appear affluent, educated, urbane, witty, nonchalant, insouciant.  In other words, far removed from the look/attitude of the average English c**t with his beer belly, nylon football shirt and piercings.
Viva Pete Campbell's old man!

Wouldn't you?  Why not?

On a clothing level - If you can afford to go out and buy the best, or most expensive. I know they're not the same thing - how much thought are you actually putting into it?

I'm sure we've all met some very well off people who dress like tramps. Or who have all the money but no class or taste.

I don't think affluence comes into it really.

This is where we need the input of a former poster like Brideshead - or, possibly, Uncle Ian.  Brideshead, from what I remember - and it is a good few years ago - lived in a very modest house (possibly in a London suburb) and spent much of his disposable income on his clothes.  He may have been one of the first men in England to wear Ralph Lauren and certain Italian labels. 
I'm sure my father always bought the very best he could afford - like Church - because he believed in making a sound investment.  But he was a working class man at a time when working class men wanted to dress well - pretty much as a matter of course.  Well, some did.

I could probably think of others.

Brideshead is from my neck of the woods and in our youth our paths crossed via pubs dancehalls clubs and clothes shops. An interesting poster with a clothes obsession like most of us here. He was more 'mix and match' when it came to Ivy, Italian, English and I think he may have become more interested in a more English look.Would be good to hear from him.

Cola desert boots, blue or off-white CVOs is the only way to go, for me! Maybe I might get some sand desert boots one day.......though the look reminds me of that guy dancing in The High Numbers (the Who) videos with the stripey long sleeve top....a good look!

Money does not bring happiness, but it does make being miserable easier to accept. Not having enough can be very stressful.

Jeans (5 pocket trousers) v tailored trousers.

Tailored trousers - with the exception of military type chinos, put you straight into old man territory. It doesn’t matter whether they are wool, corduroy or any other smart fabric that I can’t think of, these days they come across as dated in an uncool way, as opposed to dated in a way that is cool. I haven’t expressed that very well but most of you will instantly gather what I mean. They now look staid, stuffy and just don’t do a lot for any man.  Again, although you might dress for your own enjoyment, you have to consider what is worn in the real world.

Jeans - not just blue denim but any 5 pocket cut, be they twill, corduroy, moleskin, impart a different shape, if truth be told a more masculine shape, definitely a more cool silhouette. A pair of light coloured jeans worn with a natural shoulder jacket introduce that dash of informality that can be key to achieving an Ivy look.

I was watching ‘Girl in a Spiders Web’ last night, enjoyable hokum about a motorcycle riding punky Swedish girl of indeterminate sexuality who uses her skills as a hacker to do good against international criminals (Russians naturally).

Anyway, a character in the film, played by LaKeith Stanfield, was a NSA agent and to establish his credentials as a hip, go it alone maverick working within the conservative environs of DC government, he wore a brown corduroy sack jacket over a green and white Viyella type shirt, collar buttoned. I thought it was a cool look and one that I shall try to replicate when it gets cold again. Of course not being young, black and handsome might be a drawback, but I’ll do my best.

‘Tailored trousers - with the exception of military type chinos, put you straight into old man territory. It doesn’t matter whether they are wool, corduroy or any other smart fabric that I can’t think of, these days they come across as dated in an uncool way, as opposed to dated in a way that is cool. I haven’t expressed that very well but most of you will instantly gather what I mean. They now look staid, stuffy and just don’t do a lot for any man.  Again, although you might dress for your own enjoyment, you have to consider what is worn in the real world.‘

Complete nonsense.

Properly fitting trahseez look so much smarter. The added bonus is decent pockets, so you don’t have to contort yourself to remove items.

‘Old man territory’ should be embraced. It gives licence to a much better wardrobe.

Standing outside a football ground having a drink and watching the world go by- nearly everybody was wearing trainers, or that horrible footwear with a light coloured sole against a dark upper. That is even before glancing at grown ups in polyester team shirts bearing advertising.