Welcome to May where it rains all the time, at least in New England. Is it raining outside your window right this very moment? According to my iPhone, it looks like rain all week. Remember that saying "April showers bring May flowers?" That's bull -- April showers bring May showers. Don't worry though, I've got everything you need to safely trek out in to the storm. And what the hell, might you ask, do I know about rainy times? Well, let's just say my high school mascot was the Amherst Hurricanes.
Put a Sweater and Some Wool Socks On
Before you even think about water-wicking outerwear, you should make sure you've got the right stuff on underneath. You might think a sweater and socks are a no-brainer, but actually what I'm really saying is "Don't wear a hoodie and cotton socks." As cozy as a hoodie is, it will soak up all moisture, get heavier than you thought humanly possible and stick it directly to your freezing cold body.
Sames goes for your socks. If you end up in a situation where you have to lay your socks out to dry at work, cotton socks will take hours. At least wool socks will dry fast and even stay a bit warm while they're wet. If you want to go super advanced (or it's really cold) you can get smartwool, fleece or other synthetic fabrics designed for skiers. This time of year a lot of stores are having huge sales on sweaters, so it's a great time to buy. Obviously if you live in a place where there are warm showers you can skip this sweater step. (But not the sock part, wet cotton socks are seriously gross.)
Put a Raincoat On
Does this seem obvious? Perhaps it is. You're really looking at three types of raincoats: trenchcoats, athletic raincoats and anoraks. I avoid the ever-present rain poncho because it doesn't usually keep me as dry as I think it will.
If it's not raining too hard, or if you have to be somewhere fancy, you can never go wrong with a classic trench. When shopping for a trenchcoat, look for one that covers your butt and comes to at least mid-thigh, and is made of gabardine. For a femmier look, you can get a trench in a fun color with rounded shoulders, a smaller belted waist and a fuller skirt below the waist.
For a more butch look, go for a boxier cut trench in a neutral tone. I always advocate for tying the belt like a bathrobe as opposed to fastening the buckle. This is particularly true when you're going for a more masculine-of-center look. Double breasted is in style for now (especially for masculine looks) but just wait, single breasted coats will come back. They always do.
A word of caution: good quality men's trenchcoats can be extremely expensive, so it might be worth getting a more basic trench so it won't go out of style. The original trechcoat (as well as gabardine fabric itself) was invented by Thomas Burberry, and Burberry trenches remain the holy grail of rain gear. Unfortunately no one can afford them.
The Athletic Raincoat
If you're not going anywhere fancy or if it's pouring cats and dogs, you can go for a waterproof athletic cut raincoat. These are the type of raincoats that tend to have an eye less towards fashion and more towards purpose. They also tend to be the kind you can scrunch up real small in a suitcase. You want to go with this lightweight, waterproof jacket because the rubbery Mackintosh jackets (think Paddington Bear) get sweaty. In my opinion, Patagonia, Columbia and North Face make the best, longest wearing athletic raincoats, but you might find others that fit you better.
I also particularly like athletic raincoats because they tend to be pretty gender neutral. In fact, regardless of where you land on the butch-femme fashion spectrum, if you're smaller you can almost always get away with buying a little boys jacket for half the price; just watch the length of the arms. Sometimes (the best of times) these jackets come with a soft fuzzy zip-out fleece that makes them just as useful in the fall. One adorable trend in athletic raincoats is the half-zip pullover with a kangaroo pocket.
The trendiest type of rainwear these days is an anorak. An anorak (which is basically synonymous with a lightweight parka) is like a long athletic raincoat that someone sewed a shitton of pockets onto. Sometimes this is a half-zip hoodie-style raincoat with a kangaroo pouch, others it's more like a waterproof military-style jacket with a string-tie at the waist.
These coats tend to have the coverage of a trencoat with the rain resistance of an athletic coat and the pockets of cargo pants. Like trenchcoats, the more butch anoraks have a boxier shape. They also have a tie at the middle as opposed to more femme anoraks which tend to have an elastic at the middle. These coats are durable and practical, so it's worth picking one up before they go out of style. They're usability will far outlast their trendiness.
Use an Umbrella
I've noticed no one ever seems to want to carry an umbrella. But holy shit! There's water falling from the sky and you can buy something to prevent it from falling on you. Why run from awning to awning when you can carry an awning above you? While in reality you can, of course, get by without an umbrella, I believe one is critical if you're going anywhere slightly formal (such as a job interview or a wedding). You spent a lot of time getting the perfect fauxhawk and it's worth protecting. Also, a nice big umbrella is the perfect way to get closer to someone cute.
Let's make an umbrella plan. You can really go two ways with umbrellas. You can get a really nice, big umbrella and commit to carrying it around in your hand everywhere you go when it might rain, or get a ton of those little cheap ones and stick them everyone (at the office, in your car, in your bedroom, tied to your dog). A nice umbrella can cost a ton of money, so I can see why you might be avoiding that plan. On the other hand, a good quality umbrella will usually have a larger span and be more durable in heavy winds. Nicer umbrellas also have the interesting side quality where girly umbrellas look extremely femme, men's umbrellas look extremely butch, and the solid black umbrella is the ultimate androgynous, gender neutral rain tool.
You can also go for a sort of hybrid umbrella plan where you have your nice umbrella for nice occasions and obvious downpours and cheap umbrellas for unplanned rain attacks.
As a side note: you shouldn't carry your umbrella in a heavy thunderstorm though an open area. This increase your chances of getting hit by lightening and that would be terrible.
Do Something With Your Feet
Of course there is no amount of umbrellaing that will protect your feet from getting wet. Here's a bad idea: wearing leather shoes. They will get ruined and you will cry. Here's a worse idea: wearing canvas shoes (like Toms). They will instantly soak through and you will also cry.
Here's a really good idea: wear rain boots! Rain boots are the ultimate form of rain protection. I talked about rain boots in my Queer Boots 101 article and gave you a bunch of styles to choose from. That article mostly covers the knee high brightly colored femme rain boots, and I neglected to talk much about what to do in the rain if you're more butch. While tucking your pants in to high rain boots keeps your pant hem from getting soggy, it's a pretty femme look. Personally, I think a great butch rain-look is a slightly rolled up straight leg pant over a lower-rise rain boot in a military color. This looks particularly good with old school style two-tone lace-up boots like your dad used to wear to shovel the walk. This way, your feet stay dry while you're outside, but you still look fresh inside.
The major downside to rain boots is that your feet can get extremely sweaty inside them. If you're lucky enough to live in a place with warm rain showers, you might be happier in sandal or other shoe that won't get ruined. There are tons of options when it comes to rainy day sandals. The key is not to have any leather or cotton on your sandal that will take longer than a minute to dry. For a more femme look, jellies are basically the cutest shoes ever. Alternatively, a rubber flip-flop or a Keen-style open sneaker might look cute. Some nice looking sandals will promise up and down that their leather sandals are waterproof, but I would still tread carefully. Pun intended.
Regardless of your sandal choice, you should keep two things in mind. First, if you're not wearing a skirt or shorts you should definitely roll up your pant legs. Even if it's nice and warm and the rain feels good, when that soaking wet hem cools down, you're going to be miserable. Secondly, you really shouldn't go outside in sandals if you're going any place fancy. Even if you plan to change your shoes when you get there, it's really unprofessional/not classy to show up with soaking wet feet and wet flip-flops in hand. Additionally, even in warm showers your feet will soak up some water and get a bit shrivled which can make it feel weird/uncomfortable to wear dress shoes right away.
Rain Themed Accessories
Sometimes you just have to go over the top when you embrace a rainy day. I really think that nothing brightens up a rainy day like a few rainy accessories. I mean, I would seriously swoon if I showed up on an awful night and my date had on a umbrella tie clip.
Putting it All Together
I know it can feel like a drag to even bother dressing yourself, but that doesn't mean you can't bring your A game dapper cuteness to the table. Your best bet is to incorporate all your rainy day elements in to one cohesive outfit.
For example, if it's warm out you might want to wear jean shorts, a lightweight grey wool cardigan, jellies, a brightly colored athletic rain coat and carry a bright polka-dot umbrella. If it's pouring but you want a girlier look, you could wear a long anorak that fully covers a short dress and rain boots with a clear bubble-style umbrella. Alternatively, for a butcher look, you could pair fitted black pants (less fabric to get wet), a white button up and a black vest with a dark colored trench and a navy umbrella for the ultimate dreary day look.
Think about what you want your outfit to say about you and about the weather. The key is to embrace your rain coat and boots as featured articles in your look. Maybe you want to wallow in the dismal grey mist. Maybe you want to look like you totally didn't even know it was raining outside and your cute outfit just magically totally works out. Maybe you want to be the bright burst of color on a dreary day. In just the right raincoat you can be somebody's spot of sun. Yes, I'm aware it's a bit Rachel Berry, but it's a metaphor and metaphors are important. Your rainy day outfit is how you tell the world "Rain? Whatever, I got this."