"Milwaukee's winter makes us appreciate summer!"
"Milwaukee's winter makes us tougher!"
"Snow is pretty!"

Yeah, right. Winter sucks, and you can't trudge your way through the next few months without a plan.

But with a plan, you can be toasty warm when the temperatures drop well below zero.

Of course, if you have an unlimited budget, this is easy. You can buy some technologically advanced, super-high-end gear that will keep you warm. But for the rest of us, you have to pick and choose.

I first undertook this experiment in 2014, and have tweaked it each winter. I kept this entire list to under $550 (more, if you opt for the "secret weapons" at the end), and all of the following products are available either locally or easily through major online retailers – I've included the best prices at the time of publishing. But this is just one man's guide. Hope it helps.

Outerwear:

LL Bean Baxter State Parka ($279): My quest began with scoring the ultimate winter coat. I spent a ridiculous amount of time researching down fills, as well as getting opinions from reviewers, Twitter and Facebook friends.

Everyone said that the faux fur hood makes a big difference. While some friends said I should look into the Canada Goose brand, I couldn't justify spending $1,000 on a coat. I also studied parkas from North Face and Patagonia. In 2014, I bought the Marmot Thunder Bay Parka. It was warm, but not warm enough.

Last winter, I upgraded to the LL Bean model, which is rated to 45 below zero.

I'm really glad I did. So far, it's been very, very warm – on a day with 15 degree temps, I stuck my arm out the car window into the blowing wind. I felt no cold whatsoever. My friends were right, the faux fur ruff makes all the difference. My only complaints are that with so many pockets, I sometimes can't find my car keys, and it's easy to overheat when wearing the coat indoors. This is strictly a below-freezing parka, although when the temperature drops below zero, you're still gonna need something warm under the coat.

Sorel Caribou Wool Boot ($170): When your feet get cold, the rest of you will follow. When I originally wrote this, I opted for a less expensive boot, the Columbia Men's Bugaboot ($110). I now regret that purchase, because my feet still got cold, the Omni-Heat lining was scratchy, and they were pretty ugly. Last year, I upgraded to the Sorel and haven't looked back. The sherpa pile snow cuff and wool inner boot make the difference, and they look retro cool. These are definitely the warmest boots I've ever owned.

Cheap trapper ski hat ($21): I picked up a couple of hats between eBay and Amazon, all cheap, all ugly and all effective. The truth is with the warm faux fur hood of the parka, anything else is almost overkill, but there will be times this winter when you want more peripheral vision. These trapper hats are very silly and Soviet looking, but when you drop the ear flaps, they are quite warm. People may laugh at me when I walk down the street wearing one, but the only thing I'm laughing at is winter.

Clam Ice Armor Edge Mitts ($34.99): I had a few challenges in the glove department. Every time I bought a pair of gloves that looked warm, once the temperature dropped below freezing, my fingers started getting chilly. I noticed that all of the gloves I had bought had the same 40 grams of Thinsulate. To get way more insulation stuffed, I'd have to go with mittens. Finally I found these beasts, designed for ice fishing. With 150 grams of Thinsulate, they are so warm that my fingers started sweating inside them after a few minutes. They're also completely waterproof: I ran the gloves under the faucet with no ill-effects. Of course, mittens are bulky, and don't bother trying to check your phone while wearing them. But boy are they hot, and you can find them locally at Farm & Fleet.

Socks and underwear:

Duofold Men's Thermal Mid Weight Wicking Bottom ($14): I bought three different pairs of inexpensive long underwear on Amazon, but the softest, cheapest pair from Duofold is my favorite. Obviously, you can spend a lot more on long underwear, but under jeans, I haven't been cold yet – in fact, I've been a little warm in the office. My second favorite pair is the ColdPruf Men's Basic Dual Layer Base Layer Bottom, for $11. Not much of a difference, really.

Duofold Men's Mid Weight Wicking Crew Neck Top ($15): Thermal shirts feel a little like too much to me, especially because you could wear a T-shirt under my parka and stay warm. But nonetheless, I picked a very thin long-sleeved thermal shirt from Duofold, mainly because it's not like those waffle-patterned, scratchy long underwear I had as a kid. This shirt is plenty warm for me.

Wigwam Boot socks ($12.99): I bought a bunch of socks at Farm & Fleet, Marshalls and online. My only criteria was that they'd be cheap and warm. I kept my budget between $5-10 per pair, and each is doing its job nicely, especially when under the Sorels. I quite like the Woolrich Ultimate Merino socks, but the Wigwam Boot socks (rated to -40 degrees) are warmer.

Secret weapons:

Mr. Heater Big Buddy Indoor Safe Propane Heater ($109.99):  You ever try polyurethaning a table in your garage when it's 20 degrees outside? I don't recommend it. Instead, pick up this propane heater. It takes one-gallon tanks and can be used indoors for emergencies (with proper ventilation). It busts out 18,000 BTUs, which was plenty to heat up my garage, but it's not as powerful as heaters that hook directly onto a larger tank – although with an adapter, this one can. I'm a big fan on this little heater. I plan on using it tailgating or on my deck this winter. It heats up safely, in a hurry, and lasts about four hours on its highest setting.

Zippo A-Frame Hand Warmer ($14): This is a crazy invention. It looks just like a regular Zippo lighter, but a little bigger. Amazingly, it stays lit and smoldering for the entire 12 hours you have it filled up and inside your pocket. When operated correctly, it gets quite hot. It's a little clunky, however. Filling it is weird, it smells like lighter fluid, you can't really (deliberately) extinguish it, and most importantly, it goes out by accident a lot. However, there are many tricks online, and at under $15, it could become your finicky best friend this winter.

Soft Heat Micro-Plush Top Low-Voltage Electric Heated Queen Mattress Pad ($147): Where has this been all my life? It's just so obvious. If you heat your bed from below, none of the heat is lost from above like with an electric blanket. With two separate heating zones, this pad allows us to turn down our heat at night and crank up each side of the bed. Don't think about it. Just buy it this winter.