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Shoulder: Laughing Skull Shoulderpads
Chest: Runecloth Tunic
Wrists: Mystical Bracers
Hands: Shadowy Laced Handwraps
Waist: Serenity Belt
Legs: Padre's Trousers
Feet: Veteran's Dreadweave Stalkers
Shirt: Tuxedo Shirt
Main-hand: Defias Rapier
Simon was the most difficult character from Firefly to transmog, though I thought he'd be the easiest. For his weapon, I chose a sword since it seemed to be the only weapon fit for a man from high society, but it is completely optional. I'll admit the belt doesn't really go with the rest of the set, but I absolutely could not resist using it because of its name! It'd be very easy to find an alternative on the auction house, I'm sure.
As with all of the other Firefly sets, the one pictured is meant for roleplay but if you want to use it for transmogging the list of items includes everything you will need. Check out the Wowhead link under the picture to see how it looks.
Check back soon for the next Firefly crew member!