Honestly, $200-$250 is kind of the minimum to get a decent pair of good looking boots. Thursdays are pretty good for what they are, and unless you're really hard on your footwear they should last you a few resoles. But if you're looking for something to use daily and last you years and years, I'd agree with most of the other commenters and say you're probably better off going to one of the PNW boot makers like Whites, or Nick's, or JK. You'll have to double your budget, but they're well worth the money hand have hundreds of years of great reputations.

They're super expensive, but a pair of Nick's or Whites would probably do the job for you. They're handmade in the USA, and are pretty much universally agreed to be the best boots money can buy. They also have a bunch of styles so I'm sure one of them would meet your criteria.

Most of the time when you see an expiration date on something that doesn't seem like it would expire, it's referring to the plastic leeching into whatever substance is inside it, rather than the substance itself. Like bottled water for example.