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Money-wise, I don't think there is anything to gain by buying expensive shoes. I was never sold on the benefits of resoling expensive shoes vs discarding cheap ones and buying another pair of cheap shoes. And unless we're talking dirt cheap (and most likely we're not), adhesive construction shouldn't be that bad these days, meaning that the shoes shouldn't fall apart in a month or a season or so.
I will start this off saying I am happy to be proven wrong, indeed I just purchased a pair of Allen Edmonds so I would like justification on why I am wrong, but hear me out.
As a lurker I have often heard people say that it is cost effective to buy a pair of nice shoes vs cheap shoes. The typical reason is longevity, and that the nice look is simply icing on the cake and not the real reason to purchase nicer shoes. I would argue that both on a convenience side and a cost effective side buying even affordable 'step up' shoes fits neither of these.
For cost effective shoes I will use these dockers:
http://www.shoebuy.com/dockers-gordon/9180/837628
or
http://www.shoebuy.com/dockers-flagler-oxford/689975/1414167
I have worn these shoes for the past four years, and will be basing this off my experience, your results may vary. They are both currently available for $40 or less right now, and I have even seen them dip into the 30 dollar range, but will use $40. I know that these shoes last about 1.5 years with no care what so ever (with 2 pairs). They even claim they are full grain leather on their website, I have my suspicion though. They have also never caused me any hurt feet, hurt knees, hurt back, etc..
For nice shoes I will use allen edmonds:
http://www.amazon.com/Allen-Edmonds...&qid=1426424722&sr=1-1&keywords=allen+edmonds
or
http://www.amazon.com/Allen-Edmonds...&qid=1426424722&sr=1-3&keywords=allen+edmonds
The best price I can see for park aves online currently are $299, and the McAllisters are $279. Again you may find these for less, but I want to use common numbers, not the once in 2 year pricing. I have no experience so I will go based on what I have read on these forums that with a 2 pair rotation you can expect about 3 years before they need to be resoled, and that they can go through 2 resoling.
The first topic I will hit on is cost. The argument goes, yes, you will pay more buying the nicer shoe, but that in the long run the shoe will last so much longer that you will end up saving money. Taking that at face value we have $289 for the shoe (average of the two shoes above) + 2x resolings at $100 a piece (allenedmonds.com), coming out to 589 for 9 years of wear, or about $59/year for ownership per pair. Comparing this to the dockers you are looking at 6 pairs in those same 6 years. $40*6 is $240 or $24/year for ownership per pair.
The price differential doesn't stop there though. You need to add in that the dockers do not require shoe trees ($25 dollars for a pair, or about $3/year per shoe), something you don't need to worry about on the dockers because you'll be throwing them out before the leather really starts to wear from excess moisture or they develop wrinkle issues. Same thing with shoe polish, with the nice shoes you will be using $10-20 dollars worth of shoe polish and leather cream a year (adding $15 a year for those keeping up with the math) where with the dockers you can go several years on a cheap can of shoe polish.
Running tally: $77/yr for nice shoes, $25/yr for the cheapies. Even if you manage to go for seconds on the shoes, and get them for a steal at $150 a pop (I have never seen park aves for less then that) you are still looking at double the cost per year on the nice shoes.
It doesn't end there. There are two additional opportunity cost loses. With the nicer shoes you are investing the high cost up front in the beginning. The additional cost could be put in the market, towards buying a house, or towards getting a nicer suit (the price difference in the shoes easily covers the price difference from a cheap Macy's tommy hilfiger to something like a black lapel MTM suit) as your first suit. Additionally, the nice shoe will have leather soles, this is fine for a good bit of the time, but if it is raining heavily or there is snow/salt on the ground it is advisable to wear something else. This either results in needing to wear shoe covers (see below) or needing to purchase either a set of boots (another $100 minimum) or purchase the cheap shoes listed above. To add to this, because the nice shoes require rotation, a minimum of 3 pairs are required, so as to have at least 2 pairs during resoling. While these two items should theoretically prolong the life of the shoes listed above as they will have less wear on them, I am going to count this as a cost because the young man who is likely making this decision will now need to put $1000+ into just footwear in the first 2 years of his career vs $80 in footwear in the first two years of his career.
"But what about me?" I hear the young investment bankers making a ton of money say, "price is of little concern to me." Fair enough, but what about the convenience of the cheap shoes? Most people who are at the point where the cost of a fashion piece matters less are very short on time and value ease of use. In several ways the cheap shoes provide a benefit here. First, in just daily use, there is much less planning with a cheap shoe. You choose your suit, choose the shoes to go with it, if it is winter grab a coat, if it isn't walk out the door. With nice shoes you need to check the weather for rain, see if the salt trucks are coming before work or after work, and in the event of a massive downpour have some form of shoe cover or boot at the office just in case (if that is even possible, many who are starting out do not have this option). Same thing when coming home. With the cheap shoes there is no need to be careful or use a shoe horn, simply step on the back of the shoe and kick it off, you will be throwing the shoe out long before you wear out the leather on the heel. With the nice shoes, you need to be far more careful taking them off, taking the time to put the shoe tree in, and in storage. Yes, that may only be an extra 5 minutes a day between both morning and night, but over that same 9 year window that works out to 16425 minutes or 273.75 hours or 11.4 FULL DAYS of extra time spent worrying about your shoes. That is more than a full day a year just in shoe care.
The convenience isn't just in the small things, but in being able to just toss the shoes when a fluke happens. I will use two examples from my life, but there could be any number of different ones. I take the train into work, parking in a parking lot covered in all sorts of mean nasty stuff about 1/4 mile from the train. One day a water main broke, and the majority of the pathway was covered in about 3-4 inches of water and would not be fixed for several hours. I had the choice of removing my shoes, walking in socks through broken glass, gum, and who knows what else you would find in a parking lot in the middle of a city, getting back on the train and getting a cab to my car from another stop, or just walking through and ruining my shoes. Knowing that I could replace the shoes for $30 bucks I just pulled up my pant legs, went on through, put the shoes in a bag when I got to my car and tossed them when I got home without any worry. Another example from just this past winter, as I was clearing the ice off my car a large chunk fell off the hood, right onto my toes. It split the leather in two on the shoes (and cut up my toes), but I did not stress at all. Threw the shoes out, grabbed another pair, and off I went.
Of course, none of this may matter. Maybe you purchased the shoes simply because they look good (like I did). Maybe you can resole them yourself, allowing for extra costs to be saved. Maybe you go straight from your garage to an underground garage so you don't worry about the weather. Maybe I made a mistake somewhere and there really is a cost effective reason to purchase nicer shoes. I just wanted to put this out there for the young guy weighing all the options to get a dissenting view.
OP, you should leave it up. I actually read the whole thing. For those who didn't here's the summary:
"Nice shoes are more expensive than cheap shoes."