I by no means am suggesting go Country Road, just that when you start out maybe you'll like it. It's kind of a symptom of Styleforum that when someone starts out there is this need to create a hierarchy of clothes. This was one of the first things I did, ranking everything on a scale of Lowes>Brioni for suits and Dunlop volleys>Edward Green/Vass for shoes. I immediately assumed canvassed=good, fused=bad and saw everything in terms of dichotomies.
Took a long time to realise that most of this was wrong and led to me never being happy with what I purchased or wore. All the while I was telling myself that I was in to classical men's clothing because I wasn't vainly following trends and fashions like everyone else, when in reality I was just pursuing a different form of vanity trying to live up to the unspoken expectations of a forum on the internet and a clothing hierarchy in my head.
Now, when I walk out the door I try to take a good look at what I'm wearing and ask "am I trying too hard here." Best sartorial decision I've made.
Apologies for sloppy expression on my part. I mean that CR jackets are meh for me in terms of fit.
But seriously, when I was 20 years old, my wardrobe was pretty basic, with the items often used below:
1. Hanes white and black T-shirts;
2. Chambray button down from Sportscraft;
3. Navy wool blazer and tweed blazer (both thrifted);
4. Levi's 501s and CR chinos;
5. Doc Martens black leather and brown nubuck.
6. One suit dark greenish (from Roger David, I think) worn probably two to three times per year.