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Red Wing Irish Setters are what I wear everyday. Comfy, waterproof, (important on the farm), good traction sole, and you don't have to spend a fortune to get a decent boot.
I wear Milwaukee riding boots with the zip up rear entry. Size 12 with a nice ortho insert and I can wear them all day. But like any leather boot or shoe, there is a break-in period as they soften and mold to your foot.
The Red Wings that are made in the USA are great boots worth every penny. I wear the logger style, and I am in construction and on my feet 8 to 12 hrs a day in the heat or in the cold. They are comfortable as hell. I have tried others but they just don't hold up or aren't as comfortable. If your buying them mainly for riding they will be the last pair you will ever need to buy.
I own a 3 brands of boots........... Chippewa engineer boots(made in the USA) Timberlands(there ok, not the best) and a pair of WESCO BOOTS(logger type) by far the most durable, most comfortable boots I have ever owned. expensive(around $500.00) but worth it.............
Never had an issue with my full leather Santa clause style Harley boots, but for me the best comfort is when i have no inserts at all. Not even the thin stock one's.
7 Surprising Harley-Davidson Products that Are Not Motorcycles
Slideshow: The bar-and-shield logo shows up on far more than motorcycles, some of the company's most unexpected products have nothing to do with riding.
Slideshow: From the troubled AMF years to modern misfires, these bikes earned reputations for reliability issues, questionable engineering, or disappointing performance.
Crazy Bunderbike Build Looks Amazing, But Is It Impossible to Ride?
Slideshow: The Swiss custom shop has taken a Harley Softail and stretched it into something so long and low that it looks closer to a rolling sculpture than a conventional motorcycle.
Engraved Rebellion: Inside Bundnerbike's Glam Rock II
Slideshow: A standard cruiser becomes an intricate metal canvas in the hands of a Swiss custom house known for pushing Harley-Davidson platforms far beyond their factory brief.
Slideshow: Harley-Davidson's challenges aren't abstract; they show up in dropping shipments, shrinking dealer traffic, and strategic decisions that aren't yet translating into growth.