Edgy Liberty Clothing Line Launch Design

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This customer received 17 t-shirt designs from 7 designers. They chose this t-shirt design from AngryBear as the winning design.
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T-shirt Design Brief
I'm launching a brand new Clothing Line soon focused around Liberty, in more of an angstier rebellious sense than patriotic. The brand is called "DethroneTX," and should come from a young, edgy angle (take metalcore, hardcore, and deathcore (music genres) fashion for inspiration)(lots of black, whites, and brooding energy). The only real color palette adherence will be black, white, and yellow, or red in sub of yellow. Convey angst and tension, if that's at all possible, but please keep it contemporary at the same time. I made some attempts by myself to convey that message in the added files, so feel free to use it as a guide, only assumedly yours will look way more professional than mine! As far as the exact imagery, either a snake (to be on the safe side) or really anything that comes to mind is fair game! Refer to the "DARKO US" Single cover as well which takes more of a disturbing Sci-Fi direction. Ultimately, whatever direction you choose, I urge you to take that direction with all your effort, just make sure it is modern, edgy, and says something about liberty/freedom. (FYI, I'm situated in CST.)
(Realize now that a lot of designers from foreign countries may work on this project. If you have any questions about the theme, don't hesitate to contact me!)
Target Market(s)
Ages 20-30's of both sexes who are into Libertarianism & darker, moodier apparel
Font styles to use
Other font styles liked:
- Creepy OR Striking
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
- imagery and text, at the minimum. Prefer if it was only a few tones (white, black, yellow, ____) dark colors.
Nice to have
- I imagine a really great place to start, if everything I'm saying is confusing, is the Gadsden Flag ("Don't tread on me" flag). A rendition of that, or just utilizing the snake and the slogan is sufficient enough for me.
Should not have
- Should not be vibrant or bright.