Definitely would suggest a basket pipe, corn cob, or estate. An $80+ pipe does, on average, bring a better smoke, but I don't think most people have the budget to jump into a hobby that deep to start. If you're interested checkout some sponsor sites like smokingpipes.com, because they have estate sections and you can find a pretty good pipe for around $40. Also, by spending a little less on the pipe gives you more money to try different styles of tobaccos.
As far as tobacco goes, definitely get a sampler pack with an English, aromatic, perique etc. You won't know what style is best for you until you try a few. A popular starter English would be Early Morning Pipe by Dunhill, 1Q for an aromatic, and I'd suggest Robert McConnell's Scottish Cake for a perique. Another suggestion is look to see if the blend is available in bulk. If it is you can spend less money getting a 2oz. sample.
The last word of advice I could give you is, don't worry. Don't worry if you're doing it "right", or if people look down on you based on what pipes or tobaccos you like. Smoke the pipes you find attractive and smoke well for you and smoke the blends that your taste buds enjoy.