Need advice on slowly building a lean wardrobe. Suggestions on shoes and denim?

[Big Iron]

At one time I paid much more attention to the way I dressed. I'd like to get back to that point, this time by actually educating myself. For reference, I'm 32, 210 pounds, medium/muscular build. For all intents and purposes, I'm basically rebuilding my wardrobe from scratch. I don't have to dress well for work or other reasons, I'm doing this for myself

I prefer more classic looks, with a bit of edge. I have no problem pulling off most looks, but due to limited funds, I'd like to start with classic, versatile, casual staples. As money allows, I'd like to buy dressier items, a couple suits, etc. I'd rather invest in clothes that will last than buy cheap and frequent, especially since I tend to wear what I buy for a long time.

At the moment, I really need a pair of 'go-to' shoes/boots for daily wear and a couple pairs of new denim. With $500 to spend right now, I'm wondering if it'd be best to spend $400 of that on shoes and buy a couple pair of Levi's, or some other strategy.

For the shoes, I'd like to take advantage of one of these Green Monday sales, meaning I need to buy today. For versatility, I'm thinking brown would be best, and I'm looking at either a traditional boot or a brown chukka. I live in the rainy state of Oregon, so if I get a leather sole I'll likely have to have topy soles installed. Here are two I had in mind, the first of which I can get for just over $200 with the Amazon coupon. I've also been looking at the Wolverine 1000 Mile boots, which I really like, but I'm not sure if they (or the Frye's) are versatile enough for what I need.

http://www.amazon.com/gp/product/B0...rd_t=101&pf_rd_p=1955672402&pf_rd_i=679307011

http://www.amazon.com/gp/product/B00IFU4W9W/ref=gno_cart_title_0?ie=UTF8&psc=1&smid=ATVPDKIKX0DER

As for the denim, I'm not sure what the best 'bang for the buck' is right now, but that would probably be the best bet for me until I can afford better.

I really appreciate the help, guys!

 

[rbarthel]

For that price point (actually a little less) I like the Chippewa Service boot instead of the Frye: http://www.amazon.com/Chippewa-1901M25-Mens-Service-Cordovan/dp/B00J04NP8G/ref=cts_sh_2_fbt

Unfortunately I don't think Amazon coupon codes typically work on Red Wing or Wolverine 1ks, but it might be worth moving up into the $300 range and looking at Red Wing Beckmans/Iron Ranger or 1ks and just get the one pair leaving $200ish for a couple of pairs of Unbranded raw selvage.

 

[Big Iron]

For that price point (actually a little less) I like the Chippewa Service boot instead of the Frye: http://www.amazon.com/Chippewa-1901M25-Mens-Service-Cordovan/dp/B00J04NP8G/ref=cts_sh_2_fbt

Unfortunately I don't think Amazon coupon codes typically work on Red Wing or Wolverine 1ks, but it might be worth moving up into the $300 range and looking at Red Wing Beckmans/Iron Ranger or 1ks and just get the one pair leaving $200ish for a couple of pairs of Unbranded raw selvage.

That's hilarious you said that. Last night, with no replies here and the coupon expiring, I decided to go it alone and make a purchase.

My decision? The Chippewa Service Boot in Cordovan

Ended up getting them for $181 after the coupon. With my limited budget at the moment, I just couldn't justify spending the extra $119 on Red Wings or 1k's.

Now to find some denim...