The $100 Shoe Collection

I am a man who loves shoes. Wingtips, oxfords, penny loafers, tassel loafers, and boots line a bookcase in my entryway. I would estimate I have 20 pairs of quality leather shoes but I have never paid retail for any of them. The handful I have bought new were on sale and the rest were thrift store or Ebay specials. I would much rather have a lightly worn pair of quality shoes than a new glued-together made in China model. In this post I am going to briefly go over what makes a quality shoe before showing you, the reader, 5 pairs of my made in USA collection, amassed for only $100.

There are only a few places you want your shoes to be made – especially if you are buying vintage – USA, England, or Italy. Of course there are exceptions to this rule (I have an awesome pair of RM Williams boots from Australia and a pair of Herring Double Buckle Monks that were made in Spain). However, if you stick with these three countries you can almost assume the quality will be of a higher standard.

A good shoe starts with quality cow (or horse) leather. The shoe upper needs to be sewn onto the sole so that once the sole is well worn it can be replaced by a cobbler and the whole shoe doesn’t need to be discarded. This is typically called a Goodyear Welt.

The shoe collection I have acquired over the years could be considered excessive but it is a passion of mine and something that isn’t nearly as expensive as the average person might think. Let me help rid the myth that wearing nice shoes – or dressing well in general – has to be expensive.

This first pair of shoes I want to share with you is your classic chestnut brown oxford. I picked these up on Ebay for around $50. They are a great basic staple for any collection and retail for $365. This price continues to go up every year due to an increase in material costs, American labor and general inflation. They go on sale every few months if you are looking to buy new. Also look out for factory seconds that also go on sale regularly (I’d suggest getting on their mailing list if interested). I picked up these shoes to wear with navy, gray or khaki pants. I also have these in black and suggest you pick them up if you wear lots of gray or black outfits. I wore the black pair for my wedding but other than that they don’t get much use. In general, whenever I am being indecisive – or want to wear something plain on my feet as to not be too overly extravagant – I put my Allen Edmonds Park Avenues on.

Park Avenue

These oxblood wingtips by Florsheim Imperial always put me in a good mood. I picked them up on a thrift store excursion a couple of years ago for $8. I already owned a few pairs of wingtip style shoes but these were sleeker and closed-laced which helped me justify picking them up. This is a decision I have never regretted. Florsheim has been around for a long time but they no longer make many of their shoes in USA which is another reason these were such a steal. These are great if you want a little bit of style for a simple gray or navy suit with a white shirt. After wearing these regularly over the past couple years the sole is starting to split but I’m sure a cobbler can put on a fresh one for me without issue in the near future.


Flea markets are not a place I go for quality shoes so it was quite a surprise when I stumbled upon these Allen Edmonds Sanfords. I have an eagle eye when it comes to good shoes (also wool sweaters) and must have seen this pair from 50-feet away. I scurried over and picked them up – trying to look uninterested – I asked, “What do you want for these?” The lady looked up and said, “How about $7?” I was shaking as I reached in my pockets only to find lint and buttons before begging my wife (girlfriend at the time) to give me some cash as fast as she could. This is probably my best shoe find considering the near new condition and $300+ price point (exact price cannot be found since this style has been discontinued). This pair is can’t miss with charcoal, black or navy. I plan to wear these for many years to come.


When I used to think of Dexter, I thought of the serial killer on Showtime. Now I think of quality USA made vintage shoes. I found these penny loafers for $15, cleaned them up and threw them into my regular shoe rotation. The color is close to the Florsheim Imperial wingtips mentioned earlier so they get polished at the same time. A year after purchasing this pair I picked up the same pair in black – brand new in the box – on a 30% off sale for $26. And for those wondering: No, I don’t put a penny in mine but won’t judge if you do.


Lastly I wanted to share with you a pair of black tassel loafers. One friend referred to them as my “old man shoes” but I’ve never seen anyone – let alone an old man – wear these in the flesh. This pair was picked up at the same flea market I got the Sanfords – only years later – for $10. They were another pair in near new condition but I guess they were a little too contrarian for the average person. I think they are fun with any outfit, especially if worn with argyle or polka dot socks. Made in USA by Nordstom, I hope these are as well made as they appear to be.


I hope this post helped clear the air as to what kind of quality footwear you can purchase for very little funds. As stated in my last post: make a list and keep your eyes open. The 5 pairs mentioned above could challenge – and beat – most shoe rotations, all for under $100. Thanks for reading and remember: there is little excuse to wear terrible footwear.

This article has 4 comments

  1. Randee B. Reply

    Hi Steve,

    I got to this article via you and your wife’s ‘G’ wedding article. lol This one is very good information. I sent it to my 22yr old son who ALWAYS spends too much on clothes and such. I recently told he and his brother they needed a few pairs of well made shoes…and to start looking and saving for them. As you mentioned, you have to be on the hunt, sort of . lol
    It reminded me of my 20’s when I was kinda like you seeking a good expensive pair shoes or any fashion item….for CHEAP! LOlol It was exhilarating to score. lololol

    Well, I really enjoyed your article and will be back for more. Thanks

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