Jeans - I've spent 150$ on some MEK and True Religions back in the day. Not like a great pair of jeans. I'd spend up to 200$ if I really like them, but you can get a great pair for around 100$
Shoes - I've spend around 280$ for Bally's and for Yeezy's. Not going much more than that.
Sunglasses - I'm usually able to get good shades for under 100$ at Saks and Nordstrom Rack or Ebay. I do regret not getting some Gucci Shades years ago.
Watch - I've spend 250$ on a Movado watch, but I'd go around 500$ for one I love.
Jeans - Willing to spend how ever much I need to if I want them bad enough.
Shoes - Same. The most expensive pair of shoes I own were $600 regular price. Got them for $300 on sale.
Sunglasses - Same as you. Saks Off 5th, Nordstrom Rack and Neiman Marcus Outlet have treated me well over the years. Still got Gucci Aviators I bought 15 years ago from Off 5th for $150.
Watch - Not a jewelry or watch person at all, but I would spend $5000 or so for a Rolex or something if I really wanted one (I don’t).