Thanks for the replies so far guys! I'll address some of the comments below.
Originally Posted by Roscius
I have read that shoe makers recommend to allow 24 hrs of rest for shoes so that they are allowed to dry/remove moisture. Shoe trees aid with this. Im sure I read it on the menswear subforum.
But I think one pair of shoes will not suffice for work and casual occasions. Never mind all the sub categories for casual occasions.
So what you're saying is that not only do I need to spend more money, but that I need to spend even more money? Oooooooh, I'm dyyyying!
As far as work/casual/subcategories of casual; they are all the same in my life. If I wear a button up shirt to work with my jeans, people ask why I'm all dressed up. It's a very casual office/cube farm. Getting "dressed up" for me, is putting on a pair of khakis to go to dinner, because my grandparents country club doesn't allow jeans.
At least this far in my life, I've gotten away with one pair of shoes, one pair of sandals, and one pair of black cap toes for interviews, etc.
If I did get a second pair of shoes "because they need to rest for 24 hours", it would likely be the exact same pair or very similar.
Originally Posted by AAJJLLPP
Brown socks?? Where did you get that idea? Seems like a poor idea, I would stick with black/navy/grey.
This whole resoling will pay for itself us kinda nonsense. Resoles usually costs 70+ I beleive, depending on a bunch of factors. You can buy a fresh pair of clarks on sale for that or two pairs of vans on sale. DB's can be resoled but its another debate whether its worth the money for cheaper shoes.
Your 501's should last almost as long as a pair of gustins which are double the price.
What I'm saying is, don't kid youself into thinking you will save money, im not saying dont buy this stuff, im saying buy it for your own enjoyment not any monetary reasons.
Also if you want to keep the drivers hat, be honest with yourself if you can pull it off. IMO too many people look like tools in them.
Well, I can see your viewpoint since I've seen it suggested to match either your pants or your shoes, but I grew up matching my shoes when dressing up for more formal stuff, so I just stuck with that theme. I don't, however, understand your suggestion for black socks with jeans and brown shoes. That seems to go against everything I've ever known...
Well, yes, I guess the resoling was more in reference to expensive AEs. I think if I got clarks, I would just replace them as I currently do with vans/converse. I also understand a resole would basically be the cost of a new pair of shoes, but I would think good leather soles would last a bit longer than the rubber soles that I currently wear out in a year or less. Actually, even the soles themselves aren't quite worn through, it's usually that they all start delaminating around the year mark. So if I have a shoe that's not laminated, it should go longer, and the leather I think would take longer still to wear through.
So, instead of $60/year what I'm currently paying, it would be $300 now, then $70 ever 2 or 3 years?
Also, getting a nicer pair of shoes isn't so much that it would be cheaper in the long run, as it would be a nice pair of shoes that I could keep and appreciate forever. Something worth fixing and taking care of, instead of treating them as disposable.
Jeans, yes, Gustins are about double the price of 501s(if I get them on sale), and perhaps you are right, they may not last twice as long, but I suspect they would last quite a while longer just by the fact they are a heavier denim, not to mention that they haven't been pre worn out(washed). Considering I currently wear through a pair of 501s in about a year if I have 2 pairs to rotate every week, I'm considering at least giving the Raw Selvedge a shot and seeing how it compares. Who knows, maybe it turns out it isn't cost effective, or I just plain don't like the fit/wear, I could always go back to 501s.
Like you said, I am mostly looking to change because I want to/like the look. I don't think I'll actually SAVE money. I'm just trying to justify the cost increases to myself and wife. I'm not the type to buy $300 shoes if I'm going to replace them every year like I do with my $60 shoes. That's just extravagant and I can't afford it. I CAN afford it, however, if it reduces my recurring costs in some way.
Driving hat/flat cap: Well, I think I pull it off. At least noone has said I look like a tool. I think it works for me with my beard and thick hair. At least, I think my brothers look good in them, and we aren't that different looking. I'm currently growing my hair out too, so it has to look better than my in-between stage, unruly hair. I've tried fedoras, but I definitely look like a tool in those...