Sorry in advance for the longer post - but I added pictures to make it interesting! Background: I recently started meeting with clients at work and realized I was in serious need of a shoe wardrobe upgrade from the Cole-Hann-level cheapies I'd been wearing. I bought a pair of C&J Westbourne's (348 last) in Chestnut because I thought they would last forever and be super versatile. Beautiful Shoes. After wearing them 3-4 times, I've realized (A) they're not as versatile as I thought (I probably won't wear them with dark suits often because it draws more attention to my feet than I'd like), and (B) I still think about the cost - its not stressing me financially, just still seems like a lot for shoes that I'm not going to wear a ton (I like value/dollar). Shortly after I bought them, I had the need for a pair of much darker brown shoes, but since I'd already spent my short-term shoe budget on the C&Js, I opted for a pair of J.W. Nordstrom brand Adrians in dark brown for $175 because they were cheaper than AE strands' at $375 (in retrospect - a dumb move). They look OK to me for now, but I can tell the quality of the leather isn't there and they'll start to crease or something soon. So now I'm left with two pairs of brown shoes I'm not 100% pleased with. Proposal: I've read some great things about Meermin on SF and some other review sites and they seem like a great value for good shoes without spending a fortune. I'm thinking of selling my lightly used C&J and Nordstrom shoes, and reinvesting the money in two pairs of Linea Maestro Meermins - likely the 102461 or 10164 in dark brown and light brown. If I'm doing the euro/dollar and shipping math right it should run me about $311 per pair (including 1 shipping fee averaged over 2 pairs). Questions: In how many ways is this crazy? Seriously though... 1 - how much could I actually get for lightly used Westbourne's? Couldn't find any good comparables on SF forum or eBay. 2 - How comparable in quality is the Linea Maestro line compared to C&J benchgrade? 3 - Is the Linea Maestro line worth it or are they fairly indistinguishable from the classic line (which run $200/pair) 4 - how do the Meermin Olfe and New Rey lasts compare to C&J 348? Would you (A) do the trade to make the new shoes cheaper, (B) do the trade but buy something different that you would suggest (not really into AE styling), or (C) keep the C&J's as a high quality peripheral shoe and just deal with the Nordstroms till they start to look really bad, then re-asses down the road (but block the Meermin website and try to forget in the mean time).