Yay boxing-day sales!

For all I write about clothing, I’ve been sort of flailing around myself lately without a good sense of my own style. I did a bit of a jump from polo and jeans to smart business casual a while ago, and I think I jumped too far, because while I was still looking presentable I didn’t really look like me, if that makes any sense.

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. 
4.     5. 

I’m partial to #3 myself. What do you guys think?

25 responses to “Yay boxing-day sales!”

  1. #3 is alright, but I personally don’t like the… whatever it is down the side or the way the toes curve up. Don’t know if the curvature would show with feet in them or not. I suppose that might be important. :P I kinda like #4.

    I’ve recently started on the same sort of quest, except I’ve started from the “This guy is wearing a t-shirt, shorts, and sandals into the bank. Who the fuck is he?” place, opposed to yours.

  2. The ones I have are black! (With blue elastic panels, no less.) As much as I love them, I don’t want two pairs of the same boots but in different colors.

    I considered a pair of R.M.Williams jodhpurs, but they’re too expensive for me right now.

  3. Ankle cowboy boots? With elastic panels? They’re Chelseas!

    (Seriously, I think the picture’s throwing you off a bit. They’re not pointy-toed — take off the ankle-boot part and you’ve got #4.)

  4. Sneakers are a whole different story! I’ve got these right now:

    And for next summer I’ve got my argyle shoes:

    Argyle shoes

    but “brown leather casual shoes” is missing from the shoe lineup right now. (Dressier, I’ve got a pair of knockoffs of these in Chili.)

  5. For what it’s worth, I think I like the Ben Sherman’s best.

    Of course, this is coming from the girl who was drooling over Prada boots the other night, so ….

  6. I love them! I’m just not sure I love them with my jeans. They’re pretty pointy and the sole’s pretty thin. The two Bronx ones almost have commando soles and a toe box like parade boots.

    Ben Sherman toe:   Bronx toe:
    Ben Sherman sole:       Bronx sole:

    See? I’m just not sure it’s the right scale for jeans.

  7. I like 1 and 2 best, 2 better. But i don’t know that much about fashion and really, I’m a girl, not a boy. But I’d pick 2 for myself. looks the most comfortable

  8. Since I’m clearly the one who sticks to the fashion trends when it comes to footwear (see handle and/or avatar), my vote would be (in order of preference) 2, 4 or 1. Not really into the bootsy thing.

    Funny, how we’re different in terms of our priorities on this. My wife watches the fashion shows on TLC (What Not To Wear, Queer Eye for the Straight Guy, etc..), and the more I watch those, the more I’d rather send the statement ‘I don’t care’. This is probably why I let my wife decide what I should wear – she gets vetoed on the footwear though. :-)

  9. The boots, mendel… #3 all the way! (Says the guy who has been wearing full-size western/cowboy boots for, oh, maybe 10 or 12 years now.)

  10. Desert boots are coming back this year for sure. Picked up a pair of brown leatehr ones similar to your number 2 at Roots this month.

  11. Hm. I have a pair of Geox-branded shoes that are _identical_ to the Clark shoes in image #2. Anyways, I like all but #2. For you. :-)


  12. Yeah, lots of companies copy Clarks, or base designs on them at least — but that’s mostly just because Clarks has been around for a very long time, and a lot of their styles are decades old. It’s sort of the same way that a lot of dress shoe companies happen to have wingtips and captoes.