It’s a little hard for me to believe, but back in high school I was actually voted “Best Dressed.” This surprises me not because I dress like a slob these days, but because I dress like, well, a dad.

When I was a kid I remember thinking that my dad’s casual clothes looked pretty boring, but now that I have kids of my own I understand why. There are always a million things I’d rather spend money on – the mortgage, things for the kids, groceries – than new duds for myself. Whenever I’m tempted to go shopping I tell myself I’ve already got perfectly fine clothes at home. Perfectly fine, of course, except for the fact that many of them were bought before the Obama Administration. Some even before the Bush Administration!

The other day I was out in public when a well dressed guy in his twenties pointed at my T-shirt and said, “What’s ‘The Dive’?”

“It’s a submarine themed restaurant Steven Spielberg opened in Century City. I got this T-shirt when I ate there a few years ago.”

“Hmm,” the guy said. “I’ve never heard of it.”

It was only on the drive home that it occurred to me that Spielberg’s restaurant had closed down. I Googled to see when and saw – TO MY SHOCK – that it closed down in 1999! Not quite “a few years ago” as I’d told the well dressed dude. Thankfully, he didn’t know that, otherwise I would have been busted about wearing a T-shirt that was at least fourteen years old (though I’m pretty sure I bought the T-shirt when The Dive opened in 1994).

The one part of my wardrobe that’s especially hurting is cool clothes. Back in the day, when I was single and would go on dates or to clubs, I had my fair share of cool clothes, if  I do say so myself. At this point, though, I pretty much have a single “cool” shirt left, and it’s over ten years old. I actually bought it for my first date with Heather back in 2002, and have worn it many, many times since then.

Thankfully, I don’t have too many events these days where I have to look cool, so it hasn’t been an issue. But recently Heather and I were invited to a birthday party at an off the hook club (do the kids still say “off the hook?”) and I went through my closet looking for my “cool” shirt. I finally found it dozing in an easy chair with a newspaper on its lap.

“Cool shirt! I need you!”

Cool shirt woke with start. “Eh? What’s that, young man?”

“I need to wear you one more time. I’m going to a club!”

“A club? No, no, no. I can’t do a club. I’m not cool anymore.”

“Nonsense! You’re still cool! You can do this!”

“Pfft. I haven’t been cool in six years.”

“Not true! You’re timeless!”

“Do I even fit anymore? That gut of yours isn’t exactly in 2002 form.”

“Let me worry about the gut, alright, cool shirt? Now what to do you say? Will you go?”

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Two old timers: Me and my cool shirt

I’m pleased to say that cool shirt agreed to come out of retirement and accompany me to one more club. I think I looked good, too, as I turned a few heads! At least that’s what I told myself – I’m pretty sure they were actually gawking at the ancient relic that is my cool shirt.

There will come a time when I need to break down and buy some new clothes. You know, sometime between now and when James goes off to college.