Split the difference, get a safety razor. Like 10ยข per blade, and the razor/brush are dirt-cheap if you buy them off a shaving forum.
My biggest splurge item is a Canada Goose parka. I know, I know, they're trendy and expensive. But I often walk to work in -30 temperatures and holy fuck that thing is warm. For most temperatures, I only need a toque and gloves to keep me warm; perhaps I'll throw on a scarf and light fleece underneath for extremes. I used to arrive into work with my ears frozen, face pink and nose running, but now I can stroll in having barely noticed just how fucking cold it was. I have no qualms with a long wait at the bus stop with that thing on. The coyote fur trim really does an amazing job of keeping the wind off of your face. There's a reason those things were invented, and it wasn't for fashion. Plus, the dead animal's soul puts a spring in my step. The price is up to you to justify, but I like that they're made in Canada, not China. My only complaint is that the thing is too warm sometimes, so it can't really be used while doing anything more intense than mild exertion (unless it's really no-shit cold). If you can find them for cheap online, it's almost certainly a fake.
A decent cell phone case Recently I marched bravely into this decade and aquired an iPhone, which I like, and because I've treated my past, cheap-ass cell phones less than kind I bought the Lifeproof case for it, which costs as much as a lot of cellphones on their own, but the thing is awesome. It's completely waterproof, REALLY thin and can stop a tank bullet. The screen is no less sensitive. Love it. UnderArmour hoodies. Hoodies are a great tool: all season, and they help college kids conceal their embarrassing new physiques. I'm not the typed to get tricked-out in this overpriced sportswear, but their hoodies are really awesome even for the steep price. They cut a cold wind in half-- I often don't wear a coat in the winter because of them. They have a weird fabric threading that tends to creep people out but I always have at least three. I'll second Parker's nod to headphones, but I'm disgusting: $195 Stanton Pro. 100% Noise cancelling and you could hear the band doing lines in the control room during the recording of the song. Forgive me: I need the kind that will cancel the buzzing in my ear I get from shriekey drunk women whispering siren-esque lute strums of Xanadu in my ear like "ARE YOU GONNA FUCKIN' PLAY LOVE SHACK OR WHAT, MY FRIENDS AND I ARE LEAVING SOON YA...YA...YA FUCKIN' GUY!!!" Tell me shit like that doesn't want to make you pull a Double Van Gogh on yourself. And I have good reason: I have used only one pair with my business, I bought them in 2004. These guys: ...as a bonus, they have the cool little bee-booping lights on the side that are timed with the music's bass.
I bought a pair of Klipsch headphones with a mic a few years ago for about $100 and I love 'em. Our office is cramped quarters, so the noise level can get very distracting. I'll put on a compilation playlist of "concentration music" (light classical) so it blocks out the office chatter and provides the perfect background to allow me to stay focused when I'm writing case notes, running reports in excel, etc. I also wear them when I'm doing yard work (although sweat is an issue) and when I'm in the kitchen cooking and one of the kids is in the family room either playing a PS3 game or watching one of those unreal housewives shows that make my hair hurt.
Since I'm never going to put a real blade by my neck unless I'm tired of living, I had my parents drop a pretty penny to get me this bad boy. Comes with its on cleaning, oiling and charging all in one dock. Spoiler Makes me not hate shaving the few pubes I have grow on my face every 3-4 days. Also if I don't feel like shaving, shaving, the trimmer does a great job of giving me a 5pm shadow first thing in the morning.