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How to Dress for Gay Pride Weekend

06/29/2012 07:57 EDT | Updated 08/29/2012 05:12 EDT

They're back! The boys of Songs & Cigarettes are here to enlighten us on dressing for pride, so we'll let them take it away...

For many Torontonians Pride is the event that all calendars count towards. Also known as "Gay Christmas" in the LGBTQIA (lesbian, gay, bisexual, transgender, questioning, intersex, and asexual) community, Pride drapes the entire city with a giant rainbow flag and proclaims loudly to Canada (and our mayor), "WE'RE HEEEEERE"!

With such a vibrant event kicking off on June 22, we at Songs & Cigarettes found it crucial to impart some very important fashion tips to keep you looking the part and wowing Church Street during this festive occasion. Here are Braden, James, and Tim's 10 tips for dressing right during PRIDE.

As the authors are a mix of gay and straight males, this guide is predominantly aimed at that audience of dudes. However, many themes discussed (especially in #2, 3, 5, 8, 9) include some advice for all spectrums of the LGBTQIA community. Enjoy, and remember the biggest fashion tip of all is to be yourself and have fun, that's what PRIDE is all about.

NOTE: These tips do not include anything for people wishing to go in drag. Drag is an art and it is way beyond us to make fashion suggestions to a drag queen/king. That's like asking Will Smith to teach Fred Astaire to dance. We are simply not in the same league.

Dressing For Pride

1. Underwear: Picking out proper underwear during Pride is key. In some cases this is the only garment you are left with at the end of the night. With that in mind, throw away all your tighty-whiteys and restock your top drawer. The underwear market for gay men is a menagerie of colours, cuts, styles, and functions. However, good underwear should have the same effect as a good bra, lift and separate. The end goal is to have your package and buns supported, out, and turning heads. Your underwear during Pride should dictate (no pun intended) your mood that day. Black for night, colours for day. Also, in terms of style always go for boxer briefs. The reason for this is that you want to cover your upper thighs, can you imagine a less attended to part of the body (think of ingrown hairs and pasty skin). Thus, NO MANTIES! As well, stay away from anything grey, no one wants to see your sweaty boxers on stage at Buddies.

2. Risqué Wear: Dressing with a little S&M flair can be fun -- and Toronto Pride can be a great time to try something different and explore a side of yourself you haven't before. Are there a few things you like to wear in the comfort of your own home but are too afraid to take outside? Maybe you've had some compliments from a few pals that your rear-end really is too good to be covered up? Come on, show it off!

But some risqué wear can be a little, well, risky. First off, you're likely going to stand out like crazy -- but maybe that's what you're going for. Of course, some people look smashing in this type of get-up, so if it's your thing then Pride is a great way to wave that little flag. But, don't assume that it's just the "thing to do." But more importantly, chances are it will be a million degrees out during Pride, so if the sun really starts beating down, you'll be doing yourself tons of favours if you just steer clear of full-body leather. Trust me.

3. Accessories: Are you in the mood for a little trip to the dollar store for everything that glitters? Toronto Pride can be a great opportunity to bust out all your little bangles and do-dads that just seem a little silly to wear to the office every day. This is all about fun and celebration, so why not dress the part! Do you love capes? Wear a rainbow one! Do you love shiny tiaras? Make sure it's extra sparkly! And during the parade, you'll have tons of beads thrown your way, so make sure to collect all you can. Really, you can't go wrong with Pride-themed accessories. And just like Halloween, the more topical the better. It might be a little odd to wear a "Bill 13" t-shirt (in honour of the bill allowing for Gay-Straight Alliances), but everybody looks adorable in a Rob Ford mask. Also, Toronto Pride is a great time to affix rainbows on everything. There is no such thing as too much rainbow.

4. Grooming:This is dangerous ground we're treading on now. Do you go clean shaven? Grizzled? Waxed? Lumberjack? Chewbacca? Facial hair is a matter of personal preference -- as every man, woman, and child has given their opinion on the topic at some point in their lives -- so go with your most comfortable. Now, the hair is a different matter entirely. Some look to standout among the great sea of rainbows, awesomely cartoony getups, and people that do a lot more sit-ups than all three of us have or will ever do, so keep this in mind. The eye of the beholder adopts a new prescription for this wild, wacky weekend. Don't be afraid to pull that pompadour another inch higher and to add some colour to that mohawk (how 80s!). Speaking of which, let's talk naughty bits: this is the one weekend of the year where you can get away with something of a pubic masterpiece -- no butterflies, tribal designs or quotes from books you didn't actually read. A mustache? Chessboard? Alarmingly realistic design of the city's skyline? Sounds like someone has taken it to the next level. Of course, in the end, it's that same old story. As said above, the point of Pride is a city covered in glittery goodness yelling in unison "we are here." So, be there. Go with it. Razors be used! Razors be damned! Etc.!

5. Tight, tight, tight: Everyone has that part of their body that is just a little too soft/flabby/wiggly. None of this matters during Toronto Pride as the week celebrates everybody, regardless of shape or athletic ability. Of course, it doesn't hurt if you've got washboard abs (and if so, it's nearly a crime during Pride to cover up what deserves to be flaunted.) But, even if your stomach isn't particularly flat, there's no reason not to show it off. Have fun, and enjoy yourself! Oh, but you're a little too prudish? Then throw on an extra tight tee and consider yourself covered. Extra points if it still bares the belly (mesh is always a crowd pleaser, too.) If you really want to show things off, go nearly naked in a speedo. Usually it's hot enough! Just remember the sunblock. More on that below.

6. Dressing for a Float vs. Dressing for the Street: Functionality is an important consideration when dressing for Pride. By far, the biggest time to peacock and show off your drool worthy outfit is during the parade. However, there are different standards depending whether you are on a float versus on the street. When you are on a float (usually dancing) all traditional fashion faux-pas are thrown to the curb. You have full reign to put on your lime green thong, jump in a vat of glitter and wear as many boas as your neck can support. On the other hand, if you're on the street you are restricted to dressing in the usual skanky casual. If you find yourself on a float be prepared to compete with the TD Bank and Trojan Condom floats full of chiseled male models and ripped muscle men. Remember, what you lack in muscles you can make up with enthusiasm, DANCE YOUR HEART OUT! Oh...and be sure to bring a change of clothes for when you step off of the float.

7. Grindr: For those that don't know, Grindr is an app geared toward gay men that -- using the magic of geolocation and bravery -- allows unapologetic, no holds barred, hookups. There's a reason this doesn't exist (or, you know, shouldn't) for straight couples because history has proven that straight dudes are kind of the worst thing to happen across all of time and space (and for that we are sorry, ladies). But, I digress. Grindr at Pride is a dangerous game. I'm told that simply turning on the app during the weekend will actually cause your fancy smartphone to self-destruct in an explosion of messages, from the playful to the downright bold faced -- like a Baskin Robins' of gay men throwing all 31 flavours at you in one fell swoop. Besides, it's Pride, you guys! Who wants to be looking at their phone all weekend? Moreover, using a machine for the act of sex just seems so 3 a.m., right?

8.Your Parents: The best thing to wear during Pride? Love! Aww. . . . barf, barf, barf. But, it's true. Sure, Toronto Pride is a great opportunity to show off your abs and your tiara, but it's also a great time to "wear" a little family support and bring out those closest to you and show them what it's all about. If you've got friends and family who love you, but have never taken a walk down Church Street, this is a great opportunity to open their eyes to a beautiful, loving community. Sure, you might see someone in a tight speedo and oversized Rob Ford mask. But, you'll also see a wide variety of families, ages, backgrounds and histories coming together and having a great time. Nothing will look as good on you as a little love and support.

9.Sensible Items: We are in the midst of a heat-wave, Toronto, let's be sensible. Yes, it will be hotter than Dante's vacation in hell out there. Yes, you're going to be outside for the vast majority of the weekend; this includes patios, parades, parks and so forth (clothing optional, duh). Can we all ensure no one suffers from a third degree sunburn on their magic bits this weekend? Sunscreen, sunscreen, sunscreen. And don't be one of those goobers that say "Well, I'm just hoping it'll turn into a tan!" because if you haven't brought your A-game to Pride at this point, you're sure as hell not going to magically turn into a tanned Adonis/Aphrodite/other attractive Greek deity. Everyone loves everyone during Pride, just not your lobster-coloured thighs. Let us not forget how important sunglasses are, too -- particularly if you plan on scoping the sights without anyone knowing you're scoping the sights *wink, nod, thumbs up*. Double points for lowering your shades over your nose with one hand and saying something horribly, wonderfully catchphrase-like.

10. Condoms: The Ultimate Accessory:This one is pretty straightforward. However, with the amount of condom varieties available these days you should pick something flavourful and colourful. This is Pride, be safe, be happy, and get out there!

Have a safe and swell Pride from all of us at Songs & Cigarettes.