I used to be like you about clothes, and I still am in a way (polo’s and khaki 365 a year). But I found out that in most cases you get what you pay for, so spending the extra now will pay in the long run.

Have a good holiday my friend.

Man, those are some seriously nice pants. And they come in my size, which is extremely rare! [adds to wish list]

Given that you have to put on clothes everyday anyway, it doesn’t take any more time to put on a well-fitted, flattering shirt than it takes to put on a shirt you’ve owned for 8 years with grease-stains on it.

Of course, the “you” in that previous sentence is really me. Heh. The big hurdle for me is getting rid of the clothes that are no longer nice looking (stains, holes, faded colors) or no longer fit right (shrinkage, stretching, gaining/losing weight, etc.) and getting nice clothes to replace them so that everything in the closet is something that looks nice.

Since I’m a packrat, a mess, and an infrequent shopper, my closet is full of clothes that look like crap on me, with a small section dedicated to clothes that look good on me.

I think the big “revelation” for me is that you can tell when a shirt or a jacket is fitting you properly by looking at the part of the shirt where the arm/sleeve part is sewn to the shoulder part. That seam should be at the “corner” that your shoulder/arm makes. It should not hang below your shoulders. This is true for both women and men’s clothes. Once I was told this, it made it easier to see when something fit and something didn’t fit.

For pants, look at as much of yourself as you can see in a full-length mirror from the rear. Heh. I know it’s goofy, but that’s the side everyone else in the world is going to see more of, since they can’t stare down at you when they are in front of you.

I got a bunch of reasonably nice button down shirts, a couple nice ties, a few nice casual jackets, a leather jacket, and some decent shoes. I can’t say I have any “nice” pants, but that’s mostly ’cause I like the sloppy dress shirt & tie + casual painter’s pants vibe.

But that was a HUGE change from how I “normally” dress. The difference? I changed jobs, which meant that on a day-to-day basis, no one really had any expectations of what I “normally” wear.

You still relatively recently started working at Google, so re-establishing your wardrobe isn’t that big a deal. It’s really about breaking that expectation in yourself – the identity that you’re mentally stuck with. The people around you, as a whole, don’t have as much of you invested in your wardrobe as you do.