Hi everyone, this is my first post. I've been wanting to update my clothes as I know I probably look horrid to most anyone with fashion sense, but not so bad that anyone says anything... Before getting to my question, I'll try to give you an idea of my current wardrobe/style. Levi's 501 jeans, brown belt, brown Vans(currently short, brown leather converse all stars), white socks, shortsleeve button up untucked, fawn brown drivers hat. Pretty much the same thing everyday except I change my shirts. Problems I'm having is that I realize I should have been wearing brown socks all along... Also the jeans and shoes barely last me a year. I've always been a tightwad and consider $50+ for shoes, and $40+ for jeans to be extravagant. But the more research I do, I realize that the cost difference in say raw denim Gustin's will likely out way the cost difference. And a pair of quality leather shoes that can be resoled could last me a lifetime, so even if the cost $300, they would pay for themselves in 5 years. I'll be 30 this year, and it's past time I got my act together. So this is my proposed new look: proper leather shoes/boots. Brown socks. Gustin or unbranded Jeans, brown belt, long sleeved shirt tucked in, I'll probably keep the drivers hat. Would it look funny if the tan/fawn hat is lighter than the shoes/belt? Basically I'm going for this look , but I'm not Asian, I'm a bearded white guy So now to my question, finally :/ I need help with shoes. My limited research has brought me to Clark's desert boots and Allen Edmonds Strand. My thoughts/concerns/questions: * Can DBs be resoled? If so could I expect a lifetime of use from the waxed ones? Are they too casual for the occasional need to wear kahkis when the grandparents invite us to dinner at the country club? * Will the AE strands look to much like cowboy boots with jeans? Too dressy for jeans? Any other models I should consider for my purposes with a similar toe point? * Any OTHER brands/models I should be looking at that could go well with jeans and Kahkis, and can be resoled and used the rest of my life? Oh, and I should mention I don't like having to choose an outfit everyday, so the only thing that will be changed on a daily basis will be my shirt, socks, and underwear, so the shoes will be worn 300 days a year.