Any of my major sartorial purchases have turned out extremely well. Spending over $300 for a pair of shoes is a must if you want them to last more than 1 year. Indeed, anything over this price range will certainly look excellent in 10 years from now. My favourite pair of boots,
these Alden Indys, still look amazing 2 years, and probably 150 wears after I bought them.
Any suiting by Samuelsohn (Canadian) also holds up extremely well at the price.
Flame away.