Throwback Thursday: Captain Dapper Made Fashion Mistakes in 1999

It's time once again for a little stroll down Captain Dapper's memory lane. Today we're marching back to 1999. I was a baby faced 23-year-old when this photo was taken. I had only been living in Chicago for about a year, having moved from Ohio with a friend on a whim ... and with a lot of idealistic expectations.

I think one's 20's are a perfect time to be more daring with styles. You're young enough that people will find multi-colored hair and daring fashion cute. At least, that's what I was thinking in 1999. Actually, that's probably not what I was thinking. I was probably thinking that wearing a soul patch was my nod to 1960's jazz culture, the at-home streaked bleach job I did on my hair was killer and, although you can't see them here, the big, wide legged raver pants and oversized striped shirt I was wearing were totally hip. And I guess they were kind of cool at the time. I certainly wasn't the only person wearing pants that had legs so wide I could fit my whole body into one of them.

That streaky hair - well, it was a look. But, you know, It's fun experimenting with your hair when you're young. When it came to my hair, my mantra was always use it while you've got it. Frankly, I'm glad I did. Let's face it: as a middle aged man, my days with hair are numbered. I used my teens and twenties to make my hair do all sorts of things in all sorts of colors. Now that I'm in my thirties, I just want to preserve what I have left!

I've also left trendy styles in my past. I think that once a person reaches their thirties, they should start dressing with a little more class. Oh, I still squeeze myself into skinny jeans and follow other trends, but I try to keep it age appropriate. While I would have worn short shorts in my twenties, I don't go above mid thigh today.

And now, dear reader, I think you should share the fashion mistakes you made in your twenties in the comments. I'd love to hear what you wore then and how you dress now!

Image: Jason Loper, snapped by The Mister the first week we met with an old school, film camera.