Fashion 101: How I Went From an A to a DD in One Day

Image via WENN

“Statistics show (and Oprah said it too) that 85 percent of us are wearing the wrong bra size,” according to Jené Luciani, author of The Bra Book: The Fashion Formula to finding the Perfect Bra.

I had heard this and similar statistics before and was a little skeptical. How is it possible that so many of us could be so clueless? But after doing a quick survey of all the bras I owned, I was not too impressed with the fit of any of them. Had I become so complacent in bra buying that I had never once questioned my current size- 34C- that I had been wearing since high school?

To make sure I was getting the most out of this basic but crucial undergarment, I decided to go on a quest to find the perfect fitting bra.

1. The Default

I started off my journey at what I assume is ground zero for bra shopping in this country: Victoria’s Secret. A very friendly young girl with a headset greeted me as I entered. “I need a good bra that looks great under clothes.” I said to her.

“Why don’t you try our Body by Victoria bras?” she smiled. “All the way in the back to the left.”

I was expecting this. The Body campaign was the currently the main push of the brand. All over the store, not to mention the TV and the subway were gigantic posters with captions reading “A Body for Everybody” in front of an image of 5 skinny girls with identical bodies. Another caption exclaims, “I love my Body,” accompanying a photo of an impossibly proportioned teenager. Really. YOU love your body? You, a 15-year-old Brazilian with a washboard stomach, huge boobs and a bubble ass, you love your body?! You go girl!

So, okay, I entered Vickie’s a little annoyed already. But it wasn’t just the ads; I couldn’t help but have a little resentment for the big guy – er, gal. Victoria’s Secret dominates bra and underwear sales in this country, yet no one I’ve talked to ever seems completely satisfied with them. Many of us shop there by default because they are ubiquitous and relatively cheap.

I made my way to the Body by Victoria section and looked around waiting patiently for some help. When none came, I grabbed a couple of bras and went directly to the fitting room attendant and asked to be sized.

“Of course,” the young, cheerful woman smiled and took out a tape measure and wrapped it around my chest with my t-shirt still on. “34, or 36 C.” She said. “Or maybe a D.”

“Maybe a D?!” I exclaimed. I knew I had gained some weight this winter, but that seemed ludicrous.

“Well,” she said. “Just try both and see what you think.” Then she smiled and went on her way.

I was now on shaky ground. I had no idea what size I needed. I tried on some Cs and Ds in a few styles, and most things seemed to fit all right. A few styles gave me the dreaded 4-boob, and most of them had pads. That was really surprising to me. Why would a size D bra have pads? I know we all want big boobs, but a padded size D bra is a bit obscene, no? I was starting to feel a little overwhelmed. All of the bras were around $42. Not exorbitant, but enough that I wanted to be 100% about my purchase. The attendant was helping someone else now and I really needed a handholding through this process. I was now in unfamiliar territory. Messing about with Ds and pads and push-ups and multiway- I had no clue what I was doing. I felt like she had dropped a bombshell on me, and I had been abandoned with my now suddenly giant boobs, and I had no idea what to do with them. I decided that to get the attention that I craved, I’d have to go more upscale.

2. The Safe Bet

Next I headed to Bloomingdale’s, determined to find some answers and some one-on-one attention. I took the elevator to the 4th floor and headed straight back to the lingerie section. After ogling some pricey Cosabellas, I decided to search the more sensible (and cheaper) Calvin Kleins. After several minutes, the saleswoman came over and asked if I wanted to start a room.

“Can you size me?” I asked. “ I have no idea what I’m doing.”

“Yes, we do sizing,” she smiled. “Follow me.”

I followed her into the dressing room where she immediately whipped out her measuring tape and wrapped it around me.

“Um, don’t you want me to take my shirt off?”

“Nope,” she said, “It’s fine.” She studied the numbers on the tape, then glanced up at me. “So, it looks like you are a 34 or 36 B.”

“B?” I asked, confused.

“Or A,” she answered, sensing my discomfort. “Depending on the brand. Why? What do you usually wear?”

I lifted up my shirt and waited for her to correct her error. I studied her face. Blank. It’s not that I was insulted, just utterly perplexed. Now, I don’t have a huge rack or anything, but there is no way you could mistake me for an A cup. I waited for a moment for her to say something like, “Oh, I’m sorry, I was using the metric system. Silly me.” But I got nothing.

“C!” I shrieked. “I’m a C cup.”

“Well,” she said, “If a C has been fitting, then I’ll bring you a C.” She then proceeded to bring me a nice assortment of Calvin Kleins and Elle Macphersons. They all seemed to fit ok, but none of them wowed me. And the price point was around $40, the same as Victoria’s Secret. But the sizing debacle left me a little skittish. Before I plunked down another $40 on a bra, I wanted to be sure.

3. The Fantasy

I first heard about Agent Provocateur the same way you probably did – in the tabloids. Sienna Miller, Kate Moss, David Beckham or some improbably cool Brit is always spotted leaving this London lingerie outfitter with fancy little shopping bags under each arm. So I decided to give it a try.

The moment I entered the store I was greeted by a very attractive, petite woman in a pink wrap dress, a sort of nurses uniform costume. She was covered in tattoos and had a warm smile.

“Hey darlin, how can I help you?” she grinned. God, I loved this woman already.

From looking around the store, I knew this was not a place where I was going to find a basic nude-colored bra. The store looked like the back stage of the Moulin Rouge. The mannequins and racks were adorned with crazy costumes, sexy outfits, lace, leather, bras, panties and teddies.

“Um,” I said sheepishly, “I just want something that will look good under clothes.”

“Well,” she smiled. “All of our bras look good under clothes.  Do you want me to pick you out a selection of all our styles and you can try them?”

So she did. And I tried them. And I loved them. They were all gorgeous. Neon orange lace, pink-and-black-striped satin, denim, mesh, push-up, demi- they were dazzling and fantastic. The made me feel gorgeous. They made me feel like a high-class hooker, but you know, in a good way. I looked at my warped old Playtex bra on the ground. If that was a wife bra- these, these were mistress bras.

“How much?”

“$175.”

And just like that, the fantasy ended. I could maybe understand shelling out that much for a good basic. But for a neon orange lace balconette, I just couldn’t swing it.

4. The Authority

I had heard a story from a friend about a little shop in the Bargain District in New York’s Lower East Side, where a husband-and-wife team of Orthodox Jews could size you up and fit you in the perfect bra in 5 minutes flat. After all of my adventures, this is exactly what I needed. All of these choices were getting me nowhere. I wanted an authority to tell me exactly what to do. I had no idea what this place was called so I typed in ‘orthodox’ and ‘bra’ into Google was immediately directed to The Orchard Corset Shop.

I walked in and, as promised, an Orthodox Jewish man at the counter told me that I would be helped in a minute. Then, from behind the curtain, a tall, strikingly handsome woman peeked out and told me to come back. The store was like a warehouse. Dozens of unmarked shoeboxes lined the wall and the 2 dressing rooms were just sheets separating us from the rest of the shop. I was instructed to take off my top. Finally, I was going to get some hands-on help!

“Turn around,” the woman said briskly as she studied my back and then front, giving me a careful look. She then slipped her hand into my cup very quickly and nodded her head.

“You don’t have bad boobs.”

“I’m sorry?”

“You don’t have bad boobs,” she said again. “Just a bad bra.”

Now, before this moment, it had never occurred to me that ‘bad boobs’ might be to blame for my ill-fitting undergarments. But, I was nonetheless relieved.

“So you can help me?” I asked, hopeful.

“Of course,” she smiled. “I’m a perfectionist. Wait here. I’ll be back.”

She returned with a non-descript black bra. I lifted my arms like a baby, and she helped me into it.

“This is a 34C,” she explained. “Now, go walk to the mirror and back.”

I did as I was told, and when I made my way back she was shaking her head.

“Your left one. Too much jiggle! I don’t like that.”

“Oh I know, I’m lopsided,” I said sheepishly.

“Everyone is!” she corrected me. “Yes, to some extent everyone is. I have a celebrity client, she is 2 sizes difference on each boob!” I found this very reassuring. (I decided to show some restraint and not beg her to tell me who it was.) I knew this lopsidedness was an issue for some other people, but I had no idea it was so widespread. According to The Bra Book, one way to deal with this in extreme cases is to get a padded bra, then remove the pads in the larger cup. Other times, simply adjusting the straps can help.

The women brought me back a 36C, adjusted the strap on my small boob and voila- it fit like a glove.

“How much?” I asked.

“35.”

“Done.”

And so I made my first purchase of the day: a plain black bra that looks great under clothes. No cleavage, no pads, no 4-boob, and no annoying line under my shirt. Honestly, I was pretty happy. I could have been done right there, but I had one more stop, and this place books your credit card and charges a fee for missed appointments, so I was not about to skip it.

5. The Game Changer

I first heard about Bra Tenders from TV. It is the specialty shop that Clinton and Stacy always take the makeover subjects to on TLC’s What Not to Wear. Without fail, the people on the show are always wearing the wrong size. Because I had just come from a fitting, I was pretty sure that the clerk would be impressed with my level of preparedness. I was not like those clueless women on TV. I mean, I had done research!

I entered the shop, which is on the second floor of a building in the Theater District. In addition to outfitting TV makeover shows, Bra Tenders does the under things for many of the costumes on Broadway. They don’t have a storefront and are appointment only. The shop was very welcoming. I was led into a roomy dressing room with couches, mirrors and memorabilia all over the walls. I glanced around and quickly spotted several camisoles that had been signed by the likes of Kate Winslet, Kim Cattrall, Amy Sedaris and even Gloria Steinem. Ok, so, at that moment I knew I was buying whatever these people were selling. I mean, Gloria fricking Steinem would not tell me to buy a bad bra.

The sales woman came in the room and told me to strip. She asked me what size I wore and nodded as she took it all in with her eyes. She asked me what I was looking for, to which I answered the same as I had before. Something that looks good under clothes.

She returned with a crème colored demi cup with some nice flowers on the edges. The straps looked thick and sturdy. It was not the sexiest bra I had ever seen, but certainly not the plainest. She guided my arms through the loops and scooped my breasts with her hands, resting them gently in the cups. Even though there were no pads, I had mega cleavage- like an insane amount. I started to giggle.

“This is awesome.” I grinned. What size is this one?

“32 DD.”

“No!” I squealed. “That is insane.”

And truthfully, it is insane. DD is for people with big boobs. I do not have them. For a minute I started to question this whole place. Sure, great plan, tell women they are 2 sizes bigger and of course they will shell out and buy some bras.

“Um, is this right? I mean, will this translate into other brands, or is this just a special sizing thing you guys got going on?” I asked, now utterly confused.

“I can’t speak for other brands,” she said. “But we carry everyone here.” She then proceeded to tell me that most people have too big of a number and too small of a letter. Having a wider cup lets more of your boob fill it out, and the smaller number gives you less strap to work with, so essentially it is the same size. I wondered why and how they are the only game in town that seems to know this. Something seemed off, but as I studied the fit of this new magic bra, what she said made sense. It wasn’t tight. It fit well. And I had cleavage up to my chin. Perhaps it was vanity sizing, but worked, so I decided not to question it.

“What else do you got?”

I proceeded to try on a few more styles and designs. I ended up walking out the door with 2 amazing bras; one basic and one ‘fun’ bra with a checkerboard pattern and bows on it. The basic was $60 and the fun bra was $40. A little pricey, but I knew that I would be wearing these every day from now on.

The advice I would now give is this: Seek out an expert. Try Yelp or ask a friend. Don’t be afraid to venture into the unknown and let a stranger cop a feel. The more they grope, the better job they will probably do. And don’t be afraid to ask questions. Also, try the cup size advice. Try going up a cup size and down a number size. You just might find a better fit. Also, don’t forget to bring a t-shirt with you to try over your bras. There are some amazing bras out there, but the key is how it looks under your clothes.