Stormtrooping

It rains a lot here in NYC. For some of you in places where you drive everywhere, a little rain ain't a big deal. But here in Gotham — having to mostly walk everywhere — it's hard to escape the elements. Come rain, the subways start dripping overhead with liquids of dubious origins and practically every entryway pools with a biohazardous mixture of dog poop, urine, food stand meat juice and all kinds of street grime sloughing down from the street. Basically, the whole city becomes a giant petri dish where every known and unknown microorganism is having a raging party.
And that's just in warmer months. In the winter, it's a totally different kind of disaster. On sidewalks, you have to tread through slush cocktails flavored with snow, dirt, salt, and aforementioned smears of dog poop, urine, and meat juice (plus some occasional puke if you're lucky). But the real dig comes in when you miscalculate the depth of the slush pooled in every street corner as you cross the street. Next thing you know, you're ankle-deep in frozen filth.
So finally after a decade of personally suffering through this aqueous debacle, I decided to take action by investing in a pair of Hunter tall rain boots, or "wellingtons." And man, had I known how life-changing it is to own a pair, I would have done this years ago. In fact, my entire perspective on stormy days have pulled a 180. The rain and I have now become friends, and I look forward to whistling through the winter slush ahead.
There's a Buddhist teaching that goes something like this: Instead of expecting to cover the world in leather for you to walk on, cover your own feet in leather. In other words, stop complaining about getting your feet wet with muck and put on some damn wellies!
So let's take a look at some rain boots to get your feet dry and happy no matter how sinister the deluge. I found many different styles to fit varying tastes and personalities, so hope you'll find something you like. Once you get a pair, I promise you'll be glad you did. So here's the lineup....
TALL BOOTSTall boots are best because it offers the maximum amount of elemental protection. This is a great chance for you to find an excuse to wear tall boots without having to be a horseman or biker. Wear these with slim fit or straight leg jeans or pants for a rugged but sleek look. And seriously, stay away from meggings (watch this video if you don't know what they are)

 

Luxe: The Ralph Lauren Antony Rain Boot (above) is crafted in Italy in dark brown rubber and burnished calf leather trim. This is the most elegant boot I've seen as far as wellies go. If you're a man of refined taste and want to look well-studied even in the middle of a torrential downpour, hit this style.
Hunter Wellington Boots
Scottish brand Hunter is famous for their appointment as waterproof footwear suppliers to the Royal Family of England. They've been around since the 19th century and produced rain boots for the British Army for both World Wars. They're enjoying great popularity these days especially here in the US and offer many different styles, most of which are unisex. If you're out for a pair of rain boots, you really can't go wrong with this brand. I'll be covering a lot of their styles here because, in addition to their solid quality and craftsmanship, they truly offer the most choices in terms of great style and design.

Classic: The Hunter Original Wellington (above, left) is the brand's most classic model and comes in various colors. I have this in black. I love it. You'll love it too.
Equestrian: The Hunter Regent (above, right) is the one I'd like to get next. If you want a more sleek and fashionable alternative to the Original, this is it. It's simple yet sturdy and has just the right touch of streamlined sophistication for a more regal, equestrian/military vibe. 

Rugged: The Hunter Balmoral line (above and below) offers several masculine styles for a more testosterone-friendly aesthetic. Besides walking in wet city streets, these boots are also meant for outdoor sporting activities like hunting, shooting or fishing, making you impermeable to occasional "sissy man" accusations for wearing special "rain shoes." Apart from the Sovereign model (below) which comes in black and brown, the rest of the line comes in one color only: an outdoorsy/militaristic dark olive.
Military: The Hunter Balmoral Classic (above, left) strikes the perfect balance between ruggedness and style. Other models in this line such as the Bamboo Carbon (above, right) are twists on the Classic design and offer a more muscular sole and higher levels of heat insulation for cooler months. The bright red piping on top gives it a stylish edge.

Biker: According to the Hunter website, the Balmoral Sovereign (above) is "the most exclusive field boot for use in all weather, all terrain and all temperatures. A boot that turns heads in the field and town." In addition to its sturdiness and good looks, the biker vibe injects a good dose of attitude.
SHORT BOOTS
If tall boots aren't your thing or you find them cumbersome, short boots should fit the bill. Short boots are much easier to get in and out of and offer more versatility. Most guys already have some experience with wearing work boots, hiking boots or high-top sneakers, so wearing these rain boots shouldn't be such a novel idea. The best way to wear these boots is to loosely tuck in the hem of your jeans or pants in a nonchalant way.
The Hunter Original Short (below, left) is basically the Original model, but shorter. The Original Lace (below, right) is more or less the Original Short, but with laces. Your choice is simply a personal preference.

Hybrids: Hybrids are a great option if you don't want a style that's fully constructed in rubber and you want a more multi-purpose boot rather than a strict "rain boot." These half-shoes-half-utility-boots have more intricate styling details and resemble more to work boots than galoshes, allowing you to feel more like you're wearing work boots.
Classic American outdoor apparel brands have been making a comeback lately, and L.L. Bean is certainly in the mix. The Bison Bean Boot (below, left) is made of premium full-grain bison leather meant to shed rain and snow, with a supportive steel shank and rubber chain-tread bottom for superior performance. The 6" Bean Boot (below, right) is a shorter version of the Bean Boot and comes in a different type of leather. These boots offer a practical marriage of classicism, utility, versatility and solid good looks.

Sneakers: Swedish brand Tretorn has also been pushing to make a comeback, reinventing themselves as more than the simple canvas sneakers that made them so famous in the 80s. With their expertise in rubber-made products, they've been coming up lately with rubberized shoes that look like sneakers.
These two are my favorites in that they go beyond the hybrid styles above to looking more like everyday shoes. The Tretorn Klipporone (below, left) is just a good looking boot with distinct Swedish design sensibilities. It has just enough rubber on the sole and toe cap for maneuvering through inhospitable city terrain. The Strala model (below, right) looks like a simple slip-on sneaker that requires no thought except to just slip them on and walk out the door.

 
DON'TS: With all this talk about rain boots, it behooves me to cover a couple of Don'ts. I'm really sad to have to diss Converse here, but I've mulled over this boot for a few days, trying super hard to like them. But alas, I've reached the unfortunate conclusion that I can't get behind the Converse All Star Rain Boot (below, left).
As much as I love the Converse brand, heritage and products, they really laid an egg on this one. This boot minimizes the iconic All Star High Top to kitsch, looks like a toy and a cutesy mockery of itself. There's no way I can take a guy who wears them seriously, and if you do wear them and see a chick rolling her eyes to the back of her skull, that would be...uh...me. I'd better stay away from the L train to Hipsterville to avoid this boot sighting.
And as for the UGG (below, right), it's exactly what it's called: UGG. No matter what, just don't be "that guy" in a pair of UGGs. Period.