What this left me with was no idea what to shop for. I felt I was overdressing a bit for work because it's really a t-shirt-and-jeans department, except for upper management who dress quite conservatively business-casual. I'm not very conservative. So I found myself trying to find some sort of anchor, and I found it in a couple pairs of jeans.
The problem, as I see it, was that people here dress very casually, but without a whole lot of care: pleated Dockers and a poorly-fitted polo or button-down, that sort of thing. It doesn't send an "I care" message, and that's the message I do want to send. The first time I tried to fix this I did it by buying inoffensive but nice business-casual: brushed-cotton chinos, dress shirts, that sort of thing. But that felt out of place around my jeansy coworkers and it felt like I wasn't wearing something that I'd usually wear.
But I picked up a couple of pairs of jeans lately, dark and raw denim, slim straight fit (at Bluenotes, of all places -- for $30 and $10), and while trying them on with some shirts in my closet I had an "Aha!" moment: If I dress up chinos-and-a-shirt I don't feel like I fit in with my coworkers, but if I dress up jeans and a shirt then I'm getting somewhere. This sort of look, without the tie, and not as.. posed.
So with that in mind and the abovementioned $10 jeans on, I went out shopping last night, picked up a couple more shirts from America (for $20 and $30, regular $70), and a peacoat from Club Monaco ($100 off), and it was the easiest and most fun shopping trip I've had in ages, which makes me think I'm on the right track.
So yay! But I need new shoes and I'm having a hard time deciding what I want. I want brown boots or shoes to wear with slim jeans, stacked or cuffed.
My current options (click for details):
1. 2. 3.
I'm partial to #3 myself. What do you guys think?