I saved this one for Friday because it seemed like kind of a Casual Friday look to me. (Full disclosure: these pictures were taken on a Tuesday.) I feel like if I were a guy, this would be the kind of oufit I’d try to get away with most often. Not that he doesn’t look great, but there is something to be said for comfort.

Alec

Button-down: GAP, Shirt: H&M, Jeans: Levi’s 511s, Shoes: Clarks Chukkahs, Glasses: Warby Parker

I feel like this deserves a caption but I don’t even know what to say.

How would you characterize your style?
Cool guy? I don’t know. My style is beyond characterization.

What are you influenced by when choosing clothes? Is there anyone whose style you admire and try to replicate?
I feel like I’ve succumbed to consumerism, but I honestly am influenced by what I see on TV and in movies, and in catalogues during the short walk from my mailbox on the first floor of my apartment building to my trash can on the fourth floor.

Is there any one person whose style I admire? No, not that I can think of. Maybe John Slattery. He is the coolest. But that’s more of an, “I wish I could dress like him,” than a thing I actually try to do. Oh and Jimmy Fallon. He has the best suits and his ties are nice too.

What’s your fashion philosophy? Do you prefer classic or trendy pieces, or a mixture of both?
I definitely do not think about fashion enough to have a philosophy. I like to be comfortable. I also like things that look sort of weird, I guess? Things with lots of buttons and zippers. But then I end up never wearing them.

Trendy vs. classic, I’m not sure. I don’t think I pay enough attention to wear trendy things, but occasionally I’ll see somebody wearing something and think it’s cool and want it. That’s how I found out about desert boots — I was at a stand-up show and the comedian was wearing them and I e-mailed him after basically saying “Yeah, yeah, good show, real funny, where’d you get those shoes?”

Also, usually when I get to something, my dad or someone older will say something like “Oh, we used to wear those when we were kids!” Mostly with shoes: Converse, which were my high school jam, and Clark’s, which are my thing now. And I’m like, “Sh*t, I thought I was being trendy for once!”

Do you have any hard-and-fast rules when it comes to fashion?
Uh, wear your size. Guys should not be showing skin except maybe a tiny part of their neck with a collared shirt. ONE BUTTON UNBUTTONED. Oh, and always always always slim-leg/skinny-leg jeans and pants. No pant legs flapping around.

What are the rules that you follow to make sure that what you’re wearing is office appropriate, yet not stuffy or super corporate?
My rule at the office for a while now has been to dress as casual as possible without getting in trouble. So far, so good. Yes, that means the occasional/not-so-occasional polo in the summer. The last time I tucked in a shirt and didn’t have a meeting to go to was a long time ago. But in terms of rules I follow to be office appropriate, they can basically be summed up with “no shorts, and close-toed shoes.” A friend at work told me a few weeks ago that nobody can get away with dressing like I do for work but me. I don’t know if that’s true, but I still beamed with pride.

Name a fashion trend that you hate.
This isn’t a trend as much as it’s a Thing That Has Been Happening For A Long Time And Always Will: dressing up fancy in the summer, when it’s a hundred damn degrees out there. Can’t we just have a gentlemen’s agreement to just dress down when it’s hot? We all want it, but we all just decide that yeah, we’ll all be equally uncomfortable when we could all easily just be comfortable. If we all wore jeans and polos to meetings, nobody would think it was weird! And we’d all be so happy! But instead we are morons, sweating in suits and ties.