A passport. I can't remember how much I paid for it, originally. They're about $120 in the U.S. now, and I would definitely recommend it at that price. Get one while you don't need it yet, because it takes a while (even longer in the U.S. now, what with Trump and the pandemic f'ing up the State Dept). If you're already planning a trip abroad and don't have your passport yet, you're already up against the clock and might have to pay extra to get it expedited. In the U.S. do pay the extra to get the little wallet-sized card, which serves as a Federal ID. I have to get mine renewed, it expired a few years ago. Come to think of that, get it renewed well before it expires. I heard through the grapevine of someone having their passport rejected as they were boarding a plane, because it was less than 60 days before its expiration. I'm unable to verify that story, but do you want to be the person who finds out the hard way? Even if it was just some donkey of a boarding agent overstepping their authority, what are you gonna do, call your Representative/MP while you're in line at the security gate?
Yeti travel mug. $30, I think. I have two, one at the office and one at home. Effectively contains spills on the off chance I knock it over, enough that I'm confident having it sitting right next to my keyboard. Pretty sturdy, too. I've dropped it onto a concrete sidewalk from a standing height, and it didn't crack or chip or anything. The little sliding piece that covers the drinking hole flew off, and I thought, "well, f***", but it turns out that it's magnetic and you can just pop it back on (being able to remove it easily makes it easier to clean around the spout, too).
Propet ankle boots. $70-$80, I think? That was years ago, and I only just wore them out. I may get another pair. They wear like shoes, but they're warm and waterproof. Great for winters in the city. You would think the ankle-height is too short, that you'd get slush and cold water slopping in over the top, but I really didn't. Once in a while, I did have to dodge around one of those pond-sized puddles that I'd just walk through with regular boots, but again, not as frequently as I would have thought. You might still want proper, tall snow boots for the day or two after it snows, but I find the ankle boots much more comfortable. Also, it's true for all shoes, imo, but doubly-so for Winter boots: Don't buy online and don't buy cheap. Go to a shoe store, try on some pairs, pay the money for good ones that fit well. Even if you live in a warm-weather climate and only occasionally visit the frozen borderland outposts of civilization like New York City, Copenhagen, or Toronto in Winter, a good pair of boots could last 15 years.
Soundbot SB221 wireless bluetooth headset. $28. I bought them a year-and-a-half ago, I use them 6 hours every day, and they're only just showing signs of wear around the folding joints. I hate earbuds, for the feel and the sound quality (you can tell audiophiles by the fact that they don't use earbuds, they use proper headphones). These have pretty decent bass, and I like the behind-the-neck design more than the over-the-top design. The battery far outlasts the battery in my phone; I've never seen the battery charge get below 80%. They fold up into a pocket of my shoulder-bag. The only complaint I have is that the bluetooth gets a little spotty when I'm walking through a big, open area like a park, but I'm not sure that wouldn't happen with any wireless headset.
