Escaping boob jail is most prevalent on summer nights: coming home after a long, lacklustre day, you lug a bag chock full of nothing and old receipts in one arm, a boulder of groceries in the next. Taking your final, fateful steps towards peace and tranquility, you reach the entrance of your castle: your front door. With two free fingers you fumble towards the depths of your pocket, reaching and stretching past some bullshit iPhone and business wallet as you fish out your keys, letting them slide into the open, patient, longing lock. Bliss.

Entering your castle, you dump the bags by the doorway, ripping off a sweaty shirt as you stumble towards the bedroom. As you unbutton your pants, you eye a flannel PJ set like it’s your long-lost sister and, maintaining eye contact, you reach behind your back to unclip a sticky, suffocating bra. As the hooks come undone, you fall into a hurricane of escape and release. The distinct twinge of freedom consumes you. You have escaped boob jail once again.

Despite all being “vaguely” familiar with the above scenario, most of us still continue to allow daily imprisonment through uncomfortable, ill-fitting bras. In a 2014 report, Women’s Wear Daily cited 64 percent of women regularly wear the wrong bra size, with 73 percent of those same women admitting that wearing an ill-fitting bra could ruin their day. Yet only 29% of women wearing the wrong size knew they were committing a size-related felony against their breasts. Beyond begging questions of whether or not most of us are secretly masochists and/or helpless victims of Victoria’s Secret blowout sales, the results conclude a majority of women do not know what a proper fitting bra is supposed to feel like.

As it turns out, given the low amount of prevalent, readily available information on bra size, the statistics aren’t surprising. Other vital everyday garments have historically placed a public emphasis on comfort and fit: shoes get their own orthopaedic doctors and specialty repair shops; jeans come with a glamorous, Levi’s-approved pass to try on dozens before finding the perfect fit; and entire business are created with the sole purpose of cleaning winter coats. This, compared to a handful of small-scale women’s wear boutiques (if you’re lucky enough to live near one) offering proper bra fittings to customers, pales in comparison. In the world of boob-support, it seems we’re out of luck.

Still, the problem of misfitting bras goes further than a lack of availability to proper fittings and sizes. From an early age we’re taught, encouraged even, to believe that bras are not supposed to be comfortable; they are supposed to be sexy. From our first training bra— a half-tank top situation that likely touted something to the effect of neon piping and planet shapes, to our first pushup, a gaping mess of hot pink satin from the sales bin at the mall—our introduction to the world of bras is rocky at best. Like most things distinctly female and pubescent, a budding relationship with bras simultaneously stands as a milestone of adulthood and of grave, deep-seeded embarrassment: celebrated in a hushed whisper, then promptly dismissed and never acknowledged again.

But it’s our propensity to disregard and overlook the importance of a proper-fitting bra that has led us here: to boob jail, where over half the population resides without so much as instructions on how to apply for release on bail pending appeal.

This is why I spoke to Anita Owen, co-owner of Toronto-based Tryst Lingerie and bra-fitter extraordinaire, to try and understand why, when it comes to boobs, we keep getting it so wrong. As she gave me my own fitting, she explained that a well-sized bra is nothing if not comfortable. Knowing that I was, in fact, wearing the right size courtesy of my fitting at Victoria’s Secret last Christmas, I nodded, telling her about how I knew that of course I was wearing the right size, but I was here just to help others figure it out. Informing me that my bra was too big in the back and too small in the cup, she instructed me to try on a different size. As I slid the foreign measurements onto my chest I instantly felt as though my upper half was floating. And, being truly released from boob jail for the first time, we spoke about the obstacles preventing others from doing the same.

Why are so many people wearing the wrong size?

Anita Owen: A lot of reasons come into play.

Ignorance and the fact that they don’t know any better is one; their parents or mother didn’t show them how to shop for bras so their misconceptions are perpetrated over the years. If you don’t know how to shop for a bra you’re likely just going to wing it and self-shop. Boutiques are not readily available in parts of the world or country. Even in some of the boutiques in smaller parts of Ontario, for example, they will have less stock. And because they have less stock, they’ll fit people for the sizes they have. That’s what usually happens in stores like La Senza or Victoria’s Secret. So you get a lot of women coming in and saying I’m a 46DDD and you put them into something that’s smaller in the back but bigger in the cup.

The other thing that’s really interesting is, because people don’t know how the sizes work and how the back and letters work together, they’re more afraid of going up in the cup and think “Oh my gosh I’m a double D, I’m a triple D, I’m an F cup” and that’s scary, those letters are scary. But, they’re not afraid to go bigger in the back, which indicates a broader, wider, bigger woman. Once you explain it and say, “You’re wearing something for a much bigger, broader woman, you’re not that big.” Then, they can understand that the bigger bust is not the issue.

I know a lot of people might think a stranger in a store measuring their breasts is a situation to avoid. What would you say to those people who might be avoiding getting fitted because they’re worried they’ll feel uncomfortable?

Anita: It depends where you’re going. A lot of the newer boutiques are less old school and hands on. No one’s actually touching your breast and we’re never seeing you unclothed. You always have a bra on. So, it’s not different than being at the beach or being seen in your swimwear. Some women do have a problem with even that but we’re pretty matter of fact about it. We skip to the chase and say things like “This is your size,” “Let me see it,” and, “Does it fit?” So it shouldn’t be uncomfortable. But, depending on the customer, we can use even more discretion. The only problem is if we can’t see what they’re trying on, we can’t fix it if it’s not the right size. So you kind of have to get over that if you want to be fit in a properly fit bra.

How can more women start wearing the right bra size? Is there anything we can do?

Anita: To start you can tell your friends if their bra size looks wrong. The front of the bra should be equal to the back of the bra. So if you see your friend with their bra all the way up their back, you know they’re wearing a back too big. If their breasts are spilling out, the cups too small. A lot of girls want their breasts pushed up and that’s not what a properly fitting bra will do. If you see your friends and their breasts are pushed way up, you can gently tell them, “I think you need to get a bigger cup.” But since that’s a look a lot of young people want that anyway, it’s a little tricky.

I was pretty confident I was wearing the right size when I came in here and had no idea I was wrong.

Anita: Well, every woman has a window of one cup size because measurements fluctuate so much within style. If you go into somewhere like La Senza and say, “I’m a 32D,” they should know that will fluctuate depending on the style. The problem is that they only have a few bra shapes. So they’re going to try and make you fit into their shapes. Somewhere more specialized can go into all the different features and benefits of all the different bras and identify which shapes and styles work best for you. The first test you can do to find out if you’re wearing the right size is try to fit two fingers around the circumference of your bra: you should be able to snugly fit two fingers around where your ribs are. If you can fit any more or less, you’re wearing the wrong size.

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Claudia McNeilly is Toronto Standard’s style writer. Follow her on Twitter.

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