Rags Against The Machine
I'm a slim woman in my early 40s—successful in my field—and I am always in jeans, a vintage ripped t-shirt, and boots. I mean, ALWAYS. Granted, I have an extremely expensive handbag and perfectly highlighted blonde hair, and I always wear winged eyeliner. My friends say that going "underdressed" like this is disrespectful and inappropriate for (corporate-type) business meetings. Are they right, or is rocking your own thing no matter what a sign of confidence? (P.S. I'd kill myself before I'd wear a blazer.)
—Punk Rock Corporate
There's actually something to be said for a person who goes into an important business meeting dressed like one of their LinkedIn endorsements is "Aggressive Panhandling."
Sure, to a lot of people, it looks like career suicide in progress. However, research by Harvard Business School's Francesca Gino suggests that rebelling against norms for business attire can make you come off as higher status than people who dress all junior CEO.
Gino ran a number of experiments that led her to this conclusion, but my favorite is from a seminar on negotiations she taught at Harvard to two different groups of bigwigs in business, government and philanthropy. For each session, she dressed in the requisite "business boring" — a dark blue Hugo Boss suit and a white silk blouse. But then, for her second session, she paired this outfit with a pair of red Converse high-tops. As she made her way to the classroom, a few fellow professors did give her the WTF-eye. However, seminar participants, surveyed after each session, guessed that she was higher in status and had a pricier consulting rate when she was wearing the red sneaks.
Gino explains that a person who is seen to be deliberately violating workplace wardrobe norms sends a message that they are so powerful that they can shrug off the potential costs of not following convention.
Anthropologists and zoologists call this a costly signal: a trait or behavior that's so wastefully extravagant and/or survival-threatening that only the highest-quality, most mojo-rific people or critters could afford to display it. This, in turn, suggests to observers (whether predators or predatory executives) that it's more likely to be legit—and not false advertising.
So, it seems your dressing all hobo honcho could actually ramp up your status in others' eyes. And let's say someone suspects you're dressing this way because you've lost it on some level—psychologically or financially. Gino writes in her book "Rebel Talent" that to signal status, it's critical that people believe an individual is "consciously choosing not to conform" and willing to assume the possible costs of that. Well, with that pricey handbag (plus the megabucks highlights and Instagram influencer winged eyeliner), you swat away any suspicions that your poorgeoisie-wear reflects actual impoverishment. Just don't be surprised if, post-meeting, as you're making a call on a bench outside the building, two kindly old ladies drop a Ziploc in your lap with socks, a granola bar, and directions to the nearest shelters.
Eye Will Always Love You
I've long been a "Shallow Hal," attracted to women's youth and physical beauty and less concerned with integrity. Not surprisingly, I keep getting into relationships with women who aren't very good people. How can I stop being so superficial?
—Man With Eyes
It isn't wrong to initially be looks-driven: "Now, she's a woman I wanna have sex with!" — as opposed to "Now, she's a woman I wanna debate on Jeremy Bentham's views on utilitarianism!"
Also, you should no more feel guilty for being drawn to young women than you would for having your taste buds be more "All aboard, baby!" for chocolate cake than for a "burger" made out of broccolini. This preference evolved to solve the "How do I pass on my genes?" problem for our male ancestors. (And no, the answer to that would not have been "Date grannies!")
However, it helps to understand what psychologist Daniel Kahneman has explained as our two thinking systems—fast and slow. Our fast system is emotion-driven, rising up automatically, and is often home to toddler-like demands: "Gimme cake!" Our slow system, the home of rational thought, needs to be forced to do its job—examining our impulses and assessing whether it's wise for us to run with them.
In other words, your problem comes from running with your initial impulse without putting it through the Department of Reasoning. Though it's natural to be led by your eyes, you need to implement a next step—assessing the character of these foxerellas before you turn them into girlfriends. (This starts with generating standards so you can determine whether a woman meets or misses them.) In short, when you tell some babe, "Honey, everything looks good on you!" one would hope that you don't eventually learn whether "everything" includes a police-issued spit mask.