I'm not sure I like the way I dress. Today, while walking through Bryant Park, I saw a European man smoking a cigarette and finishing up a cell phone conversation. He was about my age, maybe a year older. Let me break down what we were each wearing:

HIM
Navy-blue wide pinstripe two-button Italian suit with somewhat wide lapels. Dark violet dress shirt and dark pink necktie, impeccably knotted. Shiny black shoes. Wristwatch.

ME
Five year-old faded blue jeans, frayed at the cuff. Shortsleeve, train engineer blue button-down shirt by Paul Frank, a desinger who built his business cute purses and t-shirts with a monkey face on them. Silk necktie around my wrist. Black Chucks. Backpack.

Compared to this nattily dressed European man, I felt like a child — and not just because I was holding a balloon and my face was covered in ice cream cake. Lately, I've wished I had more mature clothing. I often look through my closet in the morning and feel discouraged and embarrassed by how childish my wardrobe seems. I have one pair of shoes reserved exclusively for weddings and funerals, and they're stuffed somewhere beneath more than a dozen pairs of sneakers, and one pair of Gripfast combat boots. Somehow, without realzing it, I've become one of those old guys who hangs out at bars and rock shows alongside normal youths, wearing his moth-eaten BIG BLACK t-shirt and army fatigue shorts. One of those "just grill it" dudes who still gets a boner over the prospect of free hotdogs at his buddy's cookout, or free Dasani mini-bottles in the conference room left-over from someone else's meeting.

I am not even sure I would know how to change. The thought of starting over is just too daunting, but that's exactly what I'd have to do if I were to take decisive action. I'd have to donate a lot of "DO THE BARTMAN" t-shirts to Goodwill, just to wipe the slate clean and make room for wide whale corduroys, Beatle boots and silk blouses, or whatever it is grown men are supposed to wear.

I remember when I first started watching Mr. Show on television. Bob Odenkirk and David Cross began each show by walking out onstage to chat with each other and the audience. Bob would always wear a suit and tie, while David would wear a bowling shirt or "funny" t-shirt, long shorts, and sneakers. (Sometimes he would even add a very unfortunate vintage pork pie hat.) When these episodes first aired and I was 24 years old, I thought David was much cooler, and that Bob was hopelessly corny.

Now when I look at those episodes, remembering that both of them were already in their thirties when the show was on TV, or when I saw David, pushing 40, on the Kimmel show in a Kid Millionaire t-shirt from Urban Outfitters, I actually grow a little embarrassed for Mr. Cross. (Not that he needs me to get embarrassed for him. Or wait. Maybe he does need it.) It's the same kind of cringing embarrassment I felt for myself today, standing next to that European man and his thin cigarette, as I fished a frog out the front pocket of my overalls.

I don't wish to have all the trappings that I imagine come with possessing a wide pinstripe two-button Italian suit — a subscription to The Wall Street Journal, a mini-humidor, a girlfriend with cocaine residue and skin cancer freckles between her overtanned breasts, the relentless pursuit of money for its own sake. (It is probably a further testament to my immaturity that there is still some small part of me that believes these very specific lifestyle choices are requisite for anyone who owns an expensive suit.) I just admire and fear men who can put an outfit together that doesn't include a Swatch.

There is a scene i the film Bottle Rocket that nicely captures the mix of envy, admiration and contempt I feel for men who dress like men. (I'm sure I'm para-remembering it so there will probably be some inaccuracies in my description.) Dignan (Owen Wilson) is wearing a bright yellow jumpsuit and riding a scooter, and he's talking to Anthony, who is just finishing a jog. While they're talking, Futureman (a kind of asshole jock who torments Dignan and his friends pretty much throughout the film) cruises up in his pick-up truck and, after harassing Anthony and Dignan for a bit but before driving off, shouts some sort of unkind remark about Dignan's outfit.

This leaves Dignan feeling a bit deflated, and he becomes self-conscious about his very ridiculous looking bright yellow jumpsuit. To make him feel better, Anthony says [referring to Futureman's uptight jock uniform], "Well look what he's wearing!" And Dignan, still wounded, replies in all seriousness, "Yeah, he looked pretty cool, huh?"