[[SPOILER]] Hey, dude check this thread out. The total budget is a bit higher than what youre aiming for but it might give you some good ideas about where to splurge and where to save. http://www.styleforum.net/t/167456/the-5-000-wardrobe
What size are you and what are your measurements? I cant decide between S or M. I could probably swing a S in the regular fit. Im at 39" chest and typically a 48 in most fashiony stuff. Thanks for your help!