To Nipple or Not to Nipple? Kendall Jenner Weighs In on the Debate

There are few things that can divide a fashionable crowd so effectively as when you discuss the appropriateness of going braless in the summer. There are many times where the situation is unavoidable (hello, tricksy cold-shoulder dresses and tops!), but there are also times where it's a conscious style choice—something that, for many women, can add a certain je ne sais quoi to the proceedings. It's not 1864, and you'd think we'd have moved way past such controversies, but it's still a topic that generates plenty of discussion.

Some women are entirely pro, others vehemently against, and a few in the middle who kind of, maybe, perhaps, at some point, want to but feel too secure strapped into a nice, reliable bra that it'd be a great risk to do it on any old given day. Only this week did Kendall Jenner throw her hat into the ring, stating on a post featured on her app and website entitled Free The Nipple that she really doesn't "see what the big deal is with going braless!" Her take? "I think it's cool and I really just don't care! It's sexy, it's comfortable and I'm cool with my breasts. That's it!" 

"Ultimately, unless you’re wearing a totally sheer top, where’s the harm—or offence—at showing the natural shape of your chest? Men have nipples too, after all. I think as a generation, we have become increasingly prudish about them. What kind of world accepts belfies and plumped-up cleavages, but recoils as the sight of nipples covered by a T-shirt?

"As for when to go bra-less, I can’t think of a situation when I wouldn’t. I’m not a massive fan of ultra-tight stretch jersey, so I’m usually wearing a looser-fit Breton or knit (because British weather), which definitely makes an erect nipple less noticeable anyway. But I do wear silk shirts sans bra, even in the office. If every French woman that was ever born can get away with it, why can’t we do the same this side of the Channel?

"I actually very rarely notice male attention directed to my chest—short skirts have a far more noticeable reaction—but my younger brother does give both my mum and I a lot of stick about it. We ignore completely him, of course."

"I have never not worn a bra. Unless I'm sleeping or showering. Putting on a bra is as much a part of getting dressed as is putting on bottoms. Or shoes. Now I'm not talking the Wonderbra inventions that exaggerate your breasts to Kardashian proportions, and I'm not a full-bosomed woman—so I could totally get away without wearing one or choosing those light-as-air lacy numbers that look great peeking out from under an Equipment shirt—but I'd feel naked and inappropriate even though I never look at anyone styling out that combo and think such a thing.

"I actually love that French look of nonchalance—free from underwire worn under a silk button-down or fine grey marl T-shirt. Or even a Kate Moss–esque totally bra-less outing. I get it, it's sexy and screams that you're easy-going. Too busy having fun to be worrying about bra fittings. But I'm the kind of woman who freaks out if you can see a bit of bra peeking out the top of my blouse, let alone it being a runaway boob. Would I like to be emancipated from my selection of sensible Marks & Spencer numbers? Truthfully? Yes. It's a definite case of Stockholm syndrome."

So, is the transition really such a big deal? If you want to get on board, take in a few of our top tips below…