There are plenty of affiliate links to choose from below. Full disclosure – I own ALL of this gear myself, and it’s taken me about three years or so to acquire it all. So don’t go hog-wild on a binge shopping spree, frugal friends, UNLESS you’re serious about pedaling to work and errands. Some of this gear will get you started on DIY bike repair and maintenance, which I highly recommend for long-term savings.
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You’ll note that I’ve excluded bike shorts and shirts. Starting out, it’s A-OK to wear whatever is comfortable. If your ride is more than say 10 miles, invest in some padded shorts. Find a good deal on a shirt and want to look cool? Go for it. But for the first two years of cycle commuting I did just fine with my Hanes white undershirts. (They make for decent rags later on…)
For sweet bikes that are highly versatile for street, trail, and touring, I encourage you to check out the Surly line. I ride the Surly Straggler, which is a disc brake version of their popular Cross-Check model. I got both mine and Mrs. Cubert’s off Craigslist for half the list price.