Friday, August 30, 2013

Learning how to look good.

I am terrible at dressing myself, and one of the things that Girl Scout Fiancée wants me to do for the wedding is pick out my own clothes. We have some general guidelines (it's going to be late Spring/early Summer in Florida, so something lighter, cooler, and with a touch of whimsy, as she would say) and I have some vague ideas, but this is a huge problem for me, because I literally have no idea what looks good. I've dressed myself like a programmer for my whole adult life: lots of jeans and cargo shorts, t-shirts, maybe a button-up or polo shirt if I want to look nicer, but that's about the extent of it.

If a rumpled Black Sabbath t-shirt is good enough for Robert Downey Jr., it's good enough for me.
I've lost a lot of weight and was forced to go shopping for new clothes recently, as I was basically swimming in my old clothes (I wore some old khaki shorts until the point where even my belt wouldn't keep them from falling down my ankles) and realized just how deeply in trouble I am when it comes to dressing myself. I took Girl Scout Fiancée to the store and she picked out some shirts and jeans and shorts for me that, in the end, did look pretty good on me, but I have no way to gauge that for myself. I've accepted the fact that I have no fashion sense, and that it's a miracle that I can dress myself at all. Of course, when you work in an office full of gamers, just wearing a button-up shirt and slacks suddenly makes you the most well-dressed person there, but I've definitely been eying the kinds of things some of the executives in the office wear to try and get some kind of idea.

Lucky for me, mens' fashion is basically unchanging, but it's more a challenge for me to figure out what looks good on me.  Couple that with the pressure of having to look good on my wedding day for photos that we will be keeping close for the rest of our lives, and I'm mildly freaking out. So, I've decided to start small with some basic concepts, and then try and figure it out from there.

Ladies.
I am pretty sure I want to wear a light gray suit, which should go nicely with the more casual tone we want to set and is likely to be a lighter, cooler option in the Florida heat. Girl Scout Fiancée has suggested a yellow and green tie of some kind to match the other wedding colors, including the green that she is planning on using in her dress, but that's all I really know. I have no idea about style or designers, and there's no sense worrying about it until early next year when I've reached my weight goals. Still, it doesn't hurt to think ahead.

Of course, while a lighter suit is more casual, it doesn't by default say, "whimsy" in any way. I've seen lots of photos of guys wearing vests instead of jackets (not my style), suspenders and hipster glasses (despite my residence in Seattle, this is also a no-go for me), hats, etc. None of that really does it for me. The one thing I do think I want to try is some kind of saddle shoe; I've never been able to pull that off before without looking like a schmuck, but I think in the right outfit I might be able to look good.

I like the look of this, but maybe it's just the orange...
This is going to be a struggle for me, I can already tell. Trying to figure out how to look good, after fifteen years of not caring at all, is going to be tough, and frankly not something I am likely to enjoy. Still, I owe it to Girl Scout Fiancée (and myself) to look my best, and it would be nice for someone to look at our wedding photos and be able to say that I cut a handsome figure.

UPDATE: Girl Scout Fiancée liked my idea, and found a style that might work for me.

This is the Giorgio Brutini Trentt shoe.

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