Gear

Running should technically be the least expensive sport but there's a million and one ways to spend money on gear.

I'm not a gear fanatic. From other pursuits I know that sort of behavior can be distracting and isn't too much of a deal breaker. Choose a decent pair of shoes, clothing with decent mobility and breathability, and you're good to get started.

Shoes

Currently I'm wearing factory second (allegedly cosmetically flawed but I don't see it) New Balance M3190v2 shoes that cost me $50 out the door at the New Balance Factory Store in Boston. They're assembled in the USA, lightweight and have just the right padding.

They're fairly durable too. They still have a bit of life left in them after 200 miles — 15 of which was the intense Double Dipsea trail run — and they're just starting to show some wear on the outer edges near my smallest toes touch up against the fabric.

Shorts

Go for comfort and utility here. Are you planning to want to put anything in pants pockets? Make sure your pants have a zipper. I have a pair of Brooks shorts that have a big zippered pocket on the side which I prefer to the smaller back pocked that can't hold much other than keys.

Shirts

Avoiding chaffing is really the most important factor here. Bloody nipples are a real thing (mine haven't done this but they've gotten pretty sore).

Socks

So many people with some many different opinions. Find socks that don't cause your feet to get soaked/blistered. Different materials work for different types of people.