T-shirt Design Project

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This customer received 24 t-shirt designs from 11 designers. They chose this t-shirt design from DC Pro as the winning design.
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T-shirt Design Brief
We need a t-shirt design for a promotion around our roofing accessory products (ridge ventilation). Our company, Benjamin Obdyke, makes construction products for the roof and wall. Ridge ventilation is very competitive and there's very little differentiation across products. We'd like to see if we can stand out from the crowd by offering a free t-shirt with every purchase (will be instant-gratification style - in the product packaging itself). If this promotion is successful, we would offer a new t-shirt design every few months to keep the contractors asking for our product.
The company culture is that of "take the work seriously, but don't take yourself too seriously". We'd like to show more of this personality in our marketing efforts as it is rare in the construction industry. (if you look at the website for reference, all I can say is, WE'RE WORKING ON IT :)) We've done a t-shirt in the past with the phrase "Roofers Like it On Top" and it was a huge success. It was 10 years ago and we still have guys ask if we have any stowed away.
For the roofing contractors as a target audience, it is okay to bring humor & fun into the design/tagline. The most desirable design will be clever and playful without crossing into the overtly sexual, raunchy, chauvinistic, or demeaning. Would the average blue-collar joe be excited to get/wear this shirt?
Updates
re-uploaded logos again - used firefox this time per DesignCrowd support suggestion. Hoping they are working now!
Added Tuesday, August 06, 2013
Industry/Entity Type
Construction
Look and feel
Each slider illustrates characteristics of the customer's brand and the style your logo design should communicate.
Elegant
Bold
Playful
Serious
Traditional
Modern
Personable
Professional
Feminine
Masculine
Colorful
Conservative
Economical
Upmarket
Requirements
Must have
- Benjamin Obdyke logo on at least 1 side of the shirt.
interesting illustration - don't rely on just typography
stick to 1 or 2 colors, please
new tagline
Nice to have
- Product names:
Roll Vent, Rapid Ridge, Cougar, Xtractor Vent
OR just "RIDGE VENTILATION"
Should not have
- the same tagline as used in my example. Looking for a new idea