How to Dress Better as a Guy

One of the biggest roadblocks I run up against when advising guys on fashion is the idea that dressing well is somehow at odds with the rest of their lifestyles. Guys will claim that they’re too busy and poor to shop for new clothes. Or that they’re math grad students. Or that they live in San Francisco, where blazers are only worn ironically. But dressing well is not fundamentally about buying expensive brands or donning outlandish getups. I firmly believe that you can wear a hoodie every day and look put together, so long as it’s 1) the right fit for your body type and 2) of a consistent formality with the rest of your outfit.

I mention fit first because it’s both obvious and difficult. Style blogs hammer on fit. Men’s magazines hammer on fit. Yet fit is often hard to distinguish. Where is the line between body-skimming and skin-tight? Where should the cuff of your pants hit your foot? And what about all those trends – the baggy jeans trend, the oversized sweater trend, the boyfriend shirt trend – that seem predicated on, if anything, anti-fit? Read the rest of this entry »


Negativity can ruin the atmosphere faster than a can of freon, mostly because being around gloomy people is a miserable experience. One guy used to ask why I never invited him to play basketball with me. He’d see some of my friends shooting around and comment about how he hadn’t been included. Later that week, if I asked how things were going, he would mention that things would be better if people didn’t exclude him all the time. So why didn’t I invite him to play basketball more frequently? The answer is pretty clear. Not only was every interaction with him sour, he clearly did not like me.

Before you complain about how “there are no attractive women at Harvard,” recognize that it sounds a lot like, “women don’t want to date me, so there must be something wrong with the women.” The trouble with being negative is that you come across as bitter. My most romantically successful guy friends rarely find fault with their love interests, even after rejection, and my smartest friends are the least likely to grumble about a bad professor or an unfair class. No one misses the fact that you are trying to justify your failure by blaming someone else. Read the rest of this entry »

Drinks Conversation

Last night, a friend and I were discussing the oft-hilarious results of non-science people talking about science: in particular, a newspaper article referring to the different sizes of infinity. “There are an infinite number of multiples of 3, and an infinite number of multiples of 9,” the article goes on to say, “but there are more multiples of 3.” My friend found this highly amusing.

At the time, I laughed along. We were at a party; it was drinks conversation. But the more I thought about it, the less shocking it seemed. The idea of countable and uncountable infinities is not exactly intuitive. The idea that there exists a one-to-one correspondence between the multiples of 3 and the multiples of 9, and somehow that means they’re the same size, is also not intuitive. There’s no reason to expect that someone without a math background would be able to get it right, just like there’s no reason to expect someone who’s never had sex to make love like a porn star (although there is reason to expect a newspaper to hire a competent fact-checker). Read the rest of this entry »

Plagiarism and the Personality

Very little is new when it comes to social interaction. Your handshake, your humor, even your laugh, are probably culled from those around you. So why not make it completely explicit? The best way to gain social skills is to look to people who have them. Look, and then steal shamelessly. Don’t worry about being original, don’t worry about being creative; in fact, when you’re just starting out, chances are the things you think are unique (that crazy tall-tale, that special t-shirt), aren’t. When you’re comfortable with the rules and mores that govern how we interact, originality and creativity will follow.

My own starting point was a high school friend, two years my senior. He was a charismatic theater guy who won monologue competitions and took the lead role in all the school productions. Every day, I heard his voice over the intercom reading the morning announcements and cracking jokes. So I signed up to read the announcements along with him. During the months of October and February, we would arrive together in the school office, divide the messages about club meetings and sports games between us, and pass the telephone back and forth as we spoke into it, ushering in third period. Read the rest of this entry »