When to buy new gear?

Well depends if you want cheaper last season gear in selected sizes.. or new season full price in all sizes...

This is a tricky thing to time and a lot of factors go into it. I feel like the 2017 stuff is getting discounted heavily right now and the 2018 gear is starting to come down in terms of pricing but isn't getting blown out yet.

If you're looking for a high demand item or a really common size it might be sold out without need for heavy discounts.

What size and what particular gear are you shopping for?

If you’re in Ontario, Corbetts.com or their online/eBay store is Asogear.com are great. The 2017/18 skis have already been on sale the last month(30-40% off) so check if there is stock on skis or bindings you’re looking at in your size still.

Lots of places close during the summer like Corbetts does and they reopen in late August and will have more stock on new 2019 gear on sale(and super blow out deals on remaining 2017/18) and better stock for custom boot fitting.

So skis now if you can find them and boots late summer.

^^^^^Asogear is the shit. Their prices rock on ebay

As other said, Corbetts is the shit. Sporting life has a few sales going on too, but their prices are significantly higher.

Boots in Sept or Oct. You always want the most stock.

If you know the ski you want and its popular sept or Oct too to make sure you get them

Bindings whenever they are cheap.