You need to know that you can get a great great smoking pipe for cheap to start with. Don’t believe the hype about expensive gear. If/when you decide pipe smoking is for you can invest in higher end and more artistic pipes.
Choose a pipe:
Missouri Meerschaum - Ozark Mountain Hardwood Tobacco Pipe - Oval Bowl, Straight Bit
Missouri Meerschaum Country Gentleman Corncob Tobacco Pipe Straight
I recommend a straight vs bent stem to begin with, because they’re easier to clean.
You need a butane lighter with a soft flame, or matches. Any standard Bic will do. Personally, I like the Bic minis for portability. No torch lighters; they can can damage the pipe.
Get some pipe cleaners and some rubbing alcohol to clean your pipe.
Round out your starter kit with a Czech pipe tool - small and durable.
As far as tobacco goes, I recommend you start with Lane BCA or 1Q. These are both aromatic tobaccos (usually sweet with added toppings for aroma). Get whichever sounds best to you to start.
When you can, add Orlik Golden Sliced (Virgina), and Peter Stokkebye Proper English (full disclosure, I haven’t tried this one myself but it is a well-reviewed, simple option). Virginias are bright, grassy, sometimes citrusy, and Englishes are usually a bit more savory, with a smokey wood flavor and sometimes incense-like aromas.
All of these are high-quality tobaccos that will give you a sense of the main “families” of tobacco (aromatics, Virginias, Englishes) and help you figure out what general flavor profiles you’d like to explore next. There are many more genres of pipe tobacco, and blends of families of tobacco as well, but this will get you started.
If you get all this, it should only set you back about $40 or so, plus shipping. Maybe even less.
How to smoke a pipe, demystified:
Load your tobacco however you want, just not too tight. I like to fill once to the top and press it halfway down the bowl, then fill to the top and press to 1/3 down the bowl, then fill one last time, pressing down to just below the rim.
Light the top of the tobacco once, then let it go out (this is a “char light”). Light it again, this time drawing the flame deeper in the bowl. Don’t be afraid or frustrated with relighting whenever you need to. You’ll get the hang of it, and relighting is just part of pipe smoking.
Don’t draw deeply the way you would on a cigar. Sips are where its at to avoid tongue bite and extract the most flavor. You want the smoke to be a cool as possible when it hits your mouth, so puff slowly.
When you’re done, empty the ash out of the bowl. You may need to gently(!) scrape some out. Run a pipe cleaner moistened with rubbing alcohol through the stem, then fold in half wipe out the bowl as needed.
YouTube is your friend for seeing all this stuff in action and getting ideas.
A note about filters: You don’t have to use the filter —I don’t! That said I did at the beginning and tons of people do on the regular. Filters can help reduce tongue bite by taking some of the moisture out of the smoke. Lots of people swear by them. I recommend trying with or without and seeing which you like best. I’ve been thinking of giving them another go in some of my pipes that accept filters myself. Replace every 3 smokes or so.
That’s really all there is to it–don’t overthink it, enjoy it!