Photo to T-shirt design for historic landmark

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This customer received 36 t-shirt designs from 19 designers. They chose this t-shirt design from Fajr. as the winning design.
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Need a t-shirt design for a local historic bridge. I picture a Comfort Color Shirts with white line drawing, use the attached photo for art. Crop out big unnecessary buildings on photo, and convert to line drawing. The sailboat passing under the bridge is a multi-hull, if it could be a sleek monohull that would be better.
Shirts will be resold.
Include Text:
TARPON DOCK BRIDGE
Connecting the Cove to Downtown since 1910
Target Market(s)
Ages 16-56, mid to higher income, male and female
Industry/Entity Type
for retail sale
Font styles to use
Colors
Designer to choose only greyscale colors for use in the design.
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
- line art of the bridge with sailboat passing through
Nice to have
- image designed for back, with Tarpon Dock Bridge, connecting The Cove to Downtown since 1910 underneath
Should not have
- cartoonish drawing or fonts