Wise Guys: Is There Such a Thing as Too Much Cleavage?

cleavagephoto by Stefan Andrej Shambora

Advice from three of our guy friends. This week they answer the following: We know that men love boobs, but is there such a thing as too much cleavage? At what point — if any — does it become tacky to guys? Is it all about the situation and context?

Straight Married Guy (Matt): Yes, I guess there’s such a thing as too much cleavage. If I took a date to a wedding and she rolled up with 3/4 of her boobs out, I’d be a little embarrassed (and, okay — it’d probably turn me on at the same time). You see, my inner ape is endlessly fascinated with boobs, and seeing cleavage is always appreciated. But sometimes it’s inappropriate or tacky. I think all guys are a little schizophrenic about this. It’s like, man, that is a ridiculously cheesy outfit… but I wish I could see the rest of those boobs.

Straight Single Guy (Colin): I fall in love all over again with cleavage each day, but I guess when you really get down to it, there are a few specific contexts when it’s time to cover up. The scenarios are hard to distinguish. If you’re meeting my family, it’s a no-go on breast exposure, whereas if you’re meeting my co-workers, it’s totally okay. If we’re going to dinner, take them out, but if it’s Sunday brunch you might want to keep them concealed. If you’re a woman with real class, you’ll always find a way to pull it off. But please, double check with a friend who’s not afraid to hurt your feelings before you try something like J-Lo’s 2000 Grammy dress.

Gay Committed Guy (Terence): There’s no such thing as having too much cleavage. Showing too much cleavage, however, can be a situational no-no. As the bible says, there’s a time for everything that is done on earth. Let’s look at it this way (my way): Billowing cleavage in the grocery store at 10am and I crack a wry smile. Billowing cleavage in a dance club at midnight and I break into a shit-eating grin. It’s the same as a guy with his shirt unbuttoned down to just above his navel. There’s a time for everything. The bigger question is, who can pull it off well? That’s a matter of personal taste, but I bet we all can pretty much agree on whose cleavage/chest needs some covering up when we see it.

Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. Colin Adamo is an undergrad at Yale University where he directs the biennial Sex Week at Yale; the other two are a little shy.

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21 Comments on "Wise Guys: Is There Such a Thing as Too Much Cleavage?"

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I agree wholeheartedly with A. As a proud owner of a pair of natural 38DD’s, almost any top that I wear will show cleavage even if I’m not trying. That said, I am well aware at how much attention serious cleavage garners and at times I use it to my advantage. In fact, I have some shirts that I only save for special occasions when I’m TRYING to get that attention because they’re so revealing. I dont understand the women who wear sexy tops and then complain when men stare. Hello? Don’t tell me you left the house wearing that… Read more »
I am a straight girl and even I like to look at a nice pair of boobs its just something about it. It’s just very attractive. Yes there is a point where I bet even guys are like okay just put some of that away. But for the most part if it’s a time when it really doesn’t matter, not at like a family dinner, then unless your just letting it all hang out then your most likely fine. Just watch around other girls cause there catty and will call you a slut and other bad names because there upset… Read more »
I actually get (part of) Jane’s point. A woman with a nice pair on display will literally get stared at – or bothered – by every single straight guy who walks past them all day long. I can totally understand not wanting that kind of attention or that much attention. Of course, I can ALSO relate to women who get massive validation – or sexual arousal – from having guys drool over them all day long. What I don’t get – and we’ve all heard this before – is women who sport the cleavage, but then act offended by the… Read more »


Only a few women can pull it off well–like Sophia Loren or Tyra Banks, for example. For them, somehow cleavage is part of their style and fashion and they don’t look like they’re desperately soliciting oggles. As a woman, I strongly dislike cleavage. Yes, I am well endowed and have had men stare at my breasts covered. What happened to modesty? Everyone is saying it’s a sexual turn on. Knowing that, why would you want to elicit those feelings from someone who is not your partner. Do you want your son’d friends, teachers, dirty old men having sexual thoughts about… Read more »

For the person who said “if you get mad at guys for staring then you are showing too much” your theory doesn’t stand up. I have natural 32F breasts and any slight dip in the neckline of my shirts and my cleavage pops out. Girls with big breasts cannot hide cleavage unless they wear a t-shirt of turtleneck. I guess by your books I am always showing too much. Staring is not a problem, but leering is and it’s my right to get mad – if men can leer, I can get upset – we all have our own rights


Beauty is in the eye of the beholder. I believe God meant for women’s breasts to be a sexual attraction. But, personal control is a definite help. I’ve been married to a large breasted woman since the 80’s. She is never upset with my personal enjoyment but is justifiably angry with men who gauk. So guys, please use controlled actions when observing. Be kind.