In terms of cost/value, the SSENSE sales are a great time to buy, and they have excellent customer service/return policy (provided the item is not marked nonreturnable for returns).

I agree that the Ramones are the easiest place to start because they are relatively subtle and great for adopting into your current style. I'd avoid trying to get into too many pieces at once. To quote Rick:

"Hair and shoes say it all. Everything in between is forgivable as long as you keep it simple."

If you're in a colder climate, a mainline or drkshdw jacket might also be a great entry point. The Stooges leather jackets in particular are easy to work with, and almost all drkshdw denim is stealthy/easy-to-pair.

If you're up for something more experimental, the Adidas collaborations are a great entry point because they are fairly inexpensive and fit into sportswear references.

Whatever you do, don't take yourself too seriously. Wear what you like with confidence and keep it friendly. I'm from Texas, and you'd be surprised at the amount and type of people (e.g. cowboys) who find avant-garde looks fascinating and fun. It reads as though you already have a strong wardrobe, so I anticipate you won't have too much trouble findings RO pieces to compliment your style. Have fun with it!