My analog tools don't change much. I've bought many, but in reality I use only a handful. These are the ones I now stick with.
Sketching Pens and Markers
PIlot Hi-Tec-C 0.4mm (black)
This is the black gel pen I carry in my pocket. Always with me, and unforgivingly hard and fine. It's my preferred tool for small thumbnail sketching in my pocket sketchbook and on my 8-up sheets, where I work in small areas on mostly abstract boxes and arrows. I like it for general sketching (non-work related) because the fine line makes me work light and loose in the beginning to capture an essence, but then work up details around that. On my desk, I have the Hi-Tec-C in CW&T's Pen Type A aluminum housing. If you're looking for an inexpensive, smooth-rolling, medium point pen for writing, I also like the Pilot Easy Touch Fine 0.7mm point. That's the one I use in the kitchen and for filling out forms and such.
Pentel Sign Pen (black)
These are an overlooked gem. I was a user of these for close to ten years when I lived in Park Slope, Brooklyn, until the stationery store that carried them around the block from me closed. They're soft and flow smoothly, like a 2b pencil. I love these because unlike Sharpies, they don't bleed through the thinner weight of sketchbook papers.
Sharpie Fine Point Permanent Marker (black)
This is the standby that almost everyone I know uses. It's great because the lines are broad and perfect for rough thinking. When I sketch with one, I imagine being something like a 3-5px tool or very fat 2-3b soft pencil. They bleed through most normal notebook/sketchbook paper that's under 70#. I like that using it forces you to go forward and restart if you make mistakes rather than get fussy. My Sharpie is topped with a More/Real capacitive tip cap.
Moleskine Pocket Squared Notebook
I still use the squared notebook when I'm not using my own. Since they're available at stationers everywhere, and are the perfect size for desk and bag, it's an easy choice, and well made. I prefer the hard covers over the soft ones.
Midori Traveler's Notebook
This one is a luxury, and one of those objects that I feel like I will carry for my lifetime. It's beautiful and simple—one piece of leather over a squared book inside. My only wish is that the porportions were exactly to the Moleskine Cahiers so I could replace with those. It's a little narrower and taller, which I like, but it means having to get the exact replacements. I have it in two sizes and have been using it lately for my sketchnotes. If you are in New York City or San Francisco, you can get them locally at Kinokuniya.
Loose Graph Papers
If you've been following along on this site, you know I love minimalist papers made for the job. The Wireframe and 8-up sheets are the hardest working of the graph papers I use when I'm at a desk.