Which of these work shoes is the better value?

The first is a fairly standard athletic shoe (New Balance, if that helps), save that it is fitted with softer rubber cut into a slip-resistant series of triangles. It costs about USD$70. The last pair endured for about 5–6 months before the sole came unglued.

The second is a leather boot (Red Wings, if it helps any), stitched together instead of glued, with a polyurethane sole (for slip resistance) with an uninspired tread. It costs about USD$200. I don’t know how long it will last, but the guy at the shop projected a working life of about a year and a half.

I like the idea of the boots, but my main concern is spending my money wisely.

Additionally, how long is the break-in period for a pair of work boots?—I’ve tried them on, and they’re not as comfortable as the sneakers; I suspect that it’s a matter of in-breakage.—