For my first thoughts here I've gone with old style typography to get that old school honest feel. I've used handwriting in the slogan to separate it from the logo and make it 'sound' like it is coming from the owner to create a sense of trustworthiness. The whole thing looks like it is made from metal to signify the strength that you guarantee in your products and the colours are, as you've requested, very masculine.
Any feed back on this design would be most helpful but I'll also start putting some more thought to the sporty and colourful aspect that you've requested.
#7 Here's another concept, this time using towing flags. I thought I'd put this one together as it gives a reason to add strong colour to the brand name.
I would like to see number 9 so that it would work on black, grey, and white shirts. Stands out very well on black but not sure how well it will stand out on grey and white. Also would like to see with maybe a logo with it....
Thanks for your patients, I've finally gotten the time to work on this for you...
#58 #59 Are variants of #9, showing the design on grey and black as requested.
#55 #56 #57 Show an evolved concept with a stand alone logo as requested. #52 #53 #54 Are the sam but in grayscale, a format that is often handy for stantionery and press and etc.