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Free Stylin'
Start a fashion trend by crafting each of the following stylin' hats listed below.
Free Stylin' is a 5-point achievement that requires you to craft all four Stylin' hats by first obtaining their low-drop-rate patterns from specific Outland dungeon sources.
Learn Outland Leatherworking
Before any patterns will drop for you, learn Outland Leatherworking. All four patterns are gated behind this specialization, so obtain it before farming any dungeons.
Farm Stylin' Purple Hat Pattern
Enter Shadow Labyrinth and defeat Blackheart the Inciter to obtain 
Pattern: Stylin' Purple Hat. This pattern requires Outland Leatherworking (50) to use. Farm on Normal difficulty, though the pattern also drops on Heroic.
Farm Stylin' Adventure Hat Pattern
The Pattern: Stylin' Adventure Hat drops from Durnholde Rifleman and Don C and requires Outland Leatherworking (50). Farm on Normal difficulty for the best results, as the pattern also drops on Heroic.
Craft All Four Stylin' Hats
Once you have all required patterns learned and the necessary materials gathered, craft each hat to complete the achievement. Materials include items such as 
Heavy Knothide Leather, 
Cobra Scales, 
Primal Shadow, 
Purple Dye, 
Rune Thread, 
Primal Life, 
Black Dye, 
Primal Fire, 
Red Dye, and 
Primal Earth.
Tips
Because Wowhead drop rate data includes non-Leatherworkers, the listed drop rates appear lower than they actually are — patterns only drop for Leatherworkers, so your effective drop rate is higher than shown.
Normal difficulty is the recommended farm mode, but Heroic difficulty also drops all four patterns if you want an additional lockout attempt.