I’m sure this will be a point of contention between the “too cools” the “don’t want to be too cools” the “old-schools” and the “Wuertle Fan Club” (if that exists). But I am interested in stepping my headware came up from running hats to the technical trucker hat. I am bald and a hat is a must. Traditional running hats are not super flattering and hell, I’m only 31, so might as well look “cool” on course too, regardless of the importance to others. BocoGear seems to be the leader at least in marketing, but they have non-matching kit colors so I’m in search of other options. Who wears a trucker and likes what they have?
You still need sunblock with a trucker hat. The mesh isn’t sun protective.
Trucker isn’t aero.
Go to PacSun. Buy a trucker hat that looks ‘cool’. Buy it. Rock that shit.
I wear a Quicksilver trucker hat. Whopping $10.
You still need sunblock with a trucker hat. The mesh isn’t sun protective.
Doubt the air vents in my running hat are either, but I’m going with the some protection is better than no protection line of thought. I use sunscreen regardless.
Trucker isn’t aero.
Nor is my body unfortunately.
Love my North Face hat (Mudder Trucker) and black matches everything 
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Also: More room for ice on those super-hot days maybe? Thinking of giving it a try as well…
Definitely not a “trucker hat” but I got a fishing hat with a neck veil to get protection from the sun. It probably doesn’t meet the “flattering” or “cool” part for you though. Background: I’m 29 and don’t really care about the “cool” factor and am married so don’t have to worry about impressing the ladies.
…married so don’t have to worry about impressing the ladies.
Well, there is the one… 
Have you seen the Patagonia duck bill trucker? Might be what you are looking for.
I had a friend go to the Austrailian Open a few years back and he got one of the ball boy hats which were a nice athletic hat with fabric coming down on the neck. BEST THING EVER. I coach soccer and during the summer months I wore that hat like 5 hours a day. It saved me. Now I need to find another one. I also wear hat backwards if I have sunglasses to protect neck too. But not the same. And I actually think they look cool!
The one I have is made by Columbia. It works great to offer protection when out on a run.
Patagonia makes tech. trucker hats:
http://www.patagonia.com/us/product/duckbill-trucker-hat?p=28755-0
Headsweats makes one.
Spent a whole $9 on this plain black and white one on Amazon:
Wore it in the Galveston 70.3 and loved it. Lots of extra room for ice and it breathes well. I may put a patch on it or something, but I like the simplicity of it. Matches my bike and kit colors.