Bit over your budget but id strongly recommend the Canada West Romeo Insulated boots.

Those are actually resolable due to the GYW rather than the injection molded style of chelseas. Wide toe box. Made in canada.

For a cheaper option id recommend the Jim Green Stockman. Resolable. Not insulated but ive been perfectly fine wearing them in cold boston winters with a pair of darn tough socks.

My favorite injection molded chelsea are Mongrels. I have blundstones and redbacks, but the mongrels imo are far superior. Nice wide toebox, durable, grippy sole, affordable, and made in australia.

Keep in mind that none of these will replace laced winter boot. I use mine for short walks to work, around town, etc... nothing extreme.