A Guide to Side (Boob)

My transition from wearing ambitiously padded bras to none at all was quick, comfortable, and somewhat subconscious. I used to chase the push up pad, vying for some sort of lift to measure up to my better endowed friends but then I began to embrace the sartorial freedom that came as a consolation prize for my boyish chest.

Although my bare naked ladies enjoyed the new view that a lack of shelter provided, those around me started to take offense at the sight of my acute counterparts. My pass at nonchalance had become an unwelcome distraction.

I found an answer in both Braza’s silicone petal pads and the more acceptable anomaly that is The Side Boob. My affinity for anything backless introduced me to the former and the latter came with the outfit’s territory.

Urban Dictionary defines side-boob as: A view of the female breast seen from a side; generally under loosely-fitting clothes. Very titillating (pun intended) and sexual without showing any overt nudity. Or as they say in the common tongue, inviting the lobby bartender to your hotel room and then pretending like you didn’t. 

By no means is the piece of edge-flesh as controversial as bearing the nipple, and yet on more than one occasion the men in my life have politely asked me to “cover up,” (to this, I consistently and passionately respond, “why you wanna put my boobs in a ghetto?” but that is neither here nor there). Side-boob should be celebrated for its ability to be both sexy and tasteful. It provides the perfect counterbalance to a modest high neck and remains romantic while leaving room to the imagination.

The side boob reveal is akin to the high-slit trick favored by Angelina Jolie and her evangelists. Many of my bigger breasted friends exalt the look for being cleavage’s more unassuming cousin. And while Cara Delevingne and Miley Cyrus plea with Instagram to #freethenipple, I just want to be able to make a case for side boob without making it onto a tabloid’s fashion faux pas page.

But where do you stand — do you want to see the nipple go rogue, or are you content with the red carpet dissemination of side boob? Is the edge flesh attractive, or does it just look like the anatomical equivalent of “forgetting to tuck your shirt in”? In the words of ye olde trusted US Weekly, is side boob HOT or NOT?

-Esther Levy

Visit Esther’s blog, The Philosophy of Windex here and follow her ass on Instagram here

Side boob may just hint at this being the Age of Transparency in Fashion. And, if you’re trying this look, you may want some boob tape to go with it! Or, you know, forgo the type and let your Flappin’ Annies flap freely!

  • Ana González

    Side boob: hot. For some reason is easier to free the side boob and even when you are showing something, is not vulgar… well, it depends!


  • I’m all for sideboob.

  • mojomartini

    if you have small boobs, do it. And if you’re under 36. Oh, and if you’re going somewhere fancy (not to your corner bar). And if you don’t have to wave, vote, change an overhead lightbulb, or milk a goat while wearing side-booby outfit.

    • Esther Levy

      mowing the lawn?

    • Sarah Gepner

      My husband had to mean mug someone when I did side boob at a dive bar. Apparently I was being ogled.

  • Bonnie

    Side boob it. It’s the sexy peek-a-boo without all the lipstick and rouge.

  • Aubrey Green


  • GapToothedGirl

    I’m a little shy about side boob…if it transforms into a complete one??

    XOX, Gap.


  • Side boob is really a thing these days. http://mystilettolife.com/style/2014/7/14/on-the-road

  • Jelena Keravica

    Hot! I also think a tiny tattoo right next to the boob, on the ribs, is super hot. You can be bold and show it off every once in a while, but still manage to pretend it was unintentional while looking effortless and that is super super hot 🙂

  • monkeyshines
  • Iris Nguyen

    Side boob: hot, when everything else is relatively covered.

  • The side boob can definitely be sexy if done tastefully. If you can get “the girls” to stay in place without exposing their pointy mates, I say go for it!


  • Kc O

    *A Guide to Sleavage

  • Sarah

    As a fellow member of the boyish chest club, I love a side boob. I can’t show cleavage in the usual place, so why not celebrate my braless freedom from an angle which is only shown at certain moments? It is elegant and not in-your-face. As far as amount of side boob goes, a sliver is likely the most tasteful option.

  • yunijmk

    Love sideboob. Love free the nipple. I also have a rather small chest and never fell for extra padding but I now will actively remove any removable padding. #fuckthatshit #lovemasmallboobs

  • Ajnira Muminovic

    wonderful, i love seeing it everywhere, but im thinking ppl should start talking about dress code 😀 U know u cant do that in the sch but u sure can at the night out 😀

  • Suzie

    I don’t have a small chest, and if I go bra-less I end up looking like the old women in the getting older greeting cards. As such, if anything shows on me it’s side-bra, which is like having low-rise pants with granny panties. If it works for you, though, go for it!

  • nopenopenope

    Nope. 30E here.

  • jill rubinger

    “Side boob is the new cleavage” – Aristotle

  • bong
  • Lauren Ann Long

    Side boob is necessary every once & awhile. Although when it comes to freeing the nipple completely, I say leave some things up to the imagination.

  • ombeline

    Now the question is : what size of boobs is acceptable in order to show side boobs? Somehow this may create another complex – i’m small breasted, should i not wear a bra, show a tiny side boob, but actually seeming that i have no boob at all, and feel like a 12 yo teenage girl not a voluptuous grown up women?

    • Isadora De Andrade

      I feel like all sizes are acceptable. The size of the shirt is the only thing that changes, really…

  • Natascha Elizabeth

    I love it! Unfortunately my boobs are to the bigger side… But I think it looks so sexy, yet classy, with the right outfit and attitude!

  • Tamara

    depends. this is where we members if the IBTC have our advantage. A-B cup = hot. bigger than a B = not. (in my small breasted opinion…)

  • I like the crash of cultures here. You americans are unconfortable about showing the belly button, but side-boob is acceptable! I’m brazilian and i walk around with my belly button showing with no worries, but I imagine a side-boob would shock some colleagues here…

  • Geli

    I say yes to sideboob. What about going sans bra/having your nips show?

  • atelierjen

    Being another member of the boyish club, I haven’t worn a bra since I was a desparate flat chested teenager. I moved on to “sod it I’d rather be comfortable” at college – I was at college in England when punk was at it height, so nipples were pretty much de rigueur. Side boob, within reason – great. I don’t worry about my nipples (really I’m more worried about sorting out my Rosé for this summers photos), but it does depend on what you are wearing, the finer the fabric the more obvious…

  • I am notorious for side boob, except people always tend to comment and inform me of it. I can never understand why they seem to think I left the house not knowing. Jen Lawrence’s recent side boob was fantastic, just need to take a moment to appreciate how good it was.

  • donn

    hot style , but nice

    tas ransel wanita

  • Silvia Catarina Schneegans

    Side-boobs are awesome! If I weren’t so unhappy with the shape of my boobs (giant, bulging nipples and not much more than that), I would totally go bra-less and, why not, showing off my side-boobs.

  • Ray, L

    Esther I believe I am the inspiration for this post as I can’t count how many times I’ve said “Esther I see your Boobage go put on a sweatshirt”……

  • time1865

    Great for the slut look. Bet you would be a hit at a family get together.

  • user6

    For smaller and moderate size breasts, especially if there is a substantial distance between breasts, it frequently looks even better and more attractive than “traditional” cleavage

  • Brashy Couture
  • Catalina

    not all side boobs are created equal, but for those that are god speed

  • Isadora De Andrade

    one of the mysteries of the universe: at what point in life do we stop seeing nipples as the best things ever and start thinking of them as aggressive? I’m always dumbfounded by people who take offence when they get a glance of the “pointy” part of our boobs.
    Like you don’t have one (men and women, folks)? Did none of you breastfeed? And now you’re all like “that’s yucky, get it away from me!”.

  • As someone who barely has enough to show a visible amount of frontal cleavage, side boob has been really fun to show off. I recently did a photo shoot with my roommate who’s a photographer and I had the chance to display it in a new floral cropped jumpsuit. I’m hooked!



    Image no.2!! does anyone know where that top is from?