The Story of Your Life, As Told By Your Bras

1. Training Bra

For as long as you can remember, your chest was just a chest, but now, suddenly, it is “in training.” Training for what, exactly, remains to be seen, but it seems that triangle-shaped safety nets are a crucial part of navigating the impending obstacle course. Potential hurdles include, but are not limited to: acne, mood swings, smelly armpits and unrequited love. In the midst of this turmoil, you take comfort in the daily ritual of donning two, interconnected cotton hammocks, ready and waiting to cradle the middle-school evolution of your budding boobage from puffy paint circles to Hershey Kisses to kiwis, at which point those trusty hammocks start to protest.

2. Honest-to-Goodness Practical, Skin-Colored Brassiere

Congratulations! It’s time for something with more support – a real, honest-to-goodness brassiere with hook-and-eye closures in the back and adjustable straps – skin-colored, because mom is still buying and it is an unspoken rule that all moms must remain steadfast in their appreciation for the practicality of flesh-hued undergarments. The fun news is that no matter how big your boobs are, the transition from training bra to regular bra makes you feel like Marilyn Monroe underneath all your clothes. Joke’s on you, mom.

3. Victoria’s Secret Push-Up Bra

You’re finally old enough to start purchasing your own bras unattended. Hallelujah. At the mall, the siren call of Victoria’s Secret’s pullout drawers beckons you. After you and your friends finish spraying each other with bad perfumes and giggling at the lone male shopper trying to buy an anniversary gift, you scurry into dressing rooms, arms overloaded with purple polka dots, synthetic lace trim, complicated cross-back straps (“it’s like five bras in one!” the saleswoman tells you) and, most importantly, your very first push-up. The gelatinous padding lifts your chest like a cheerful buoy on the crest of a wave. “Cleavage” is no longer just a mythical possession of television actresses and older female cousins. Your posture has never looked more regal. Scoop-neck T-shirts are about to take on a whole new identity.

4. Bralette

With college comes the age of the bralette, or occasionally, its tubular sister the bandeau. Ushered in by the rise of musical festivals (whether you actually attend them or not) and pretty much singlehandedly facilitated by Urban Outfitters, this phase often coincides with an affinity for high-waist jean shorts and gladiator sandals. Since bralettes are essentially bras that tread a fine line between underwear and outerwear, they can easily double as the crop-top cherry to your denim cutoff sundae. Comfortable, cute and timesaving: the collegiate dream.

5. Fancy, Grown-Up Lingerie

Once out of college and freshly launched upon the “real world” of adulthood, you feel an itch to invest in some fancy, grown-up lingerie, otherwise known as a matching bra-and-underwear set made of a nice-ish material like silk or satin (none of that synthetic business). You go to a boutique with a French-sounding name and select a few things to try on — maybe a “balconnet” bra and matching briefs or a demi-cup with lacy boy shorts — elegant, but not boring. You slip them on one by one inside a white-walled dressing room with a lavender curtain and soft lighting while you take sips of sparkling water offered in a tall glass. You purchase the demi-cup (the “balconnet” was a little too expensive). The first few times you wear it underneath your work clothes, you feel as though you have discovered the best-kept secret to feeling put-together, and suddenly “adulting” doesn’t seem like the world’s most ridiculous made-up word after all, even though it still annoys you when other people say it out loud.

6. That One Black Bra

A year later, you’ve lost the underwear that matches your blah bra, or you realized the bra wasn’t that comfortable anyways, or you got tired of hand-washing the both of them. You find yourself gravitating toward a single black bra that is pretty without being fussy and looks good with everything from tissue tees to cocktail dresses. You don’t even bother putting it away in your underwear drawer anymore because you know you’re going to wear it the next day anyway. It’s a lot like the philosophy around not making your bed – why do it if you’re just going back to bed 12 hours later? Instead, you hang the bra on the post of a shelf or drape it across the lip of your hamper. You realize you should probably wash it at some point — because you’ve been wearing it for months — but who even knows what the proper cadence is for bra-washing?

7. …Back to Square One

Like most things in life, your bra preferences come full circle. Midway through early adulthood, it dawns on you that, truly, no bra has ever been more comfortable than the training bras of your late childhood. So you ditch underwires and revert back to the stretchy triangular hammocks of yore, except these are intended for the audience of your older self and therefore are a touch more attractive. You’ll occasionally opt for an athleisure-style sports bra, because what are sports bras, really, except for slightly tighter, thicker training bras primed for (100% optional) cardiovascular intent?

Watch out for the next phase, though. Those flesh-colored bras you hated at 14 are lurking, inevitably, on your middle-aged horizon. And so the cycle continues.

Illustration by @CrayolaMode. 

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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