Alden Shortwings, YHBTI

As I was getting ready to write about choosing a good pair of leather dress shoes, I came across this well-written article that pretty much covers all the bases, and then some. I just had to share it with you guys. Why reinvent the wheel if it was already invented, right?

Read the article from here.

Take note that this article was written in 2008, but every piece of advice is still relevant today. It will still be relevant in 2018, and probably 3008. I can’t say that for sure, but I wouldn’t doubt me.

Don’t forget

I think one of the basic—yet most important—ideas in this article is to buy quality. Don’t sacrifice a couple dollars for a subpar shoe. You’re looking to spend at least $200-$300 brand new (or if you’re a slick eBayer, $200-$300 for a shoe that may cost $500-$600 new). There’s a reason a good shoe costs this much: the quality of the material and the quality of the construction.

Average your cost over the total days you will use said pair of shoes, and spending $200-$300 isn’t that outlandish. A quality pair will last you years, maybe decades, compared to a cheaper shoe made from synthetic material with crappy construction.

Also, a quality pair can be repaired, resoled, and refinished. There’s no point repairing a subpar shoe, so you’ll end up throwing them out and buying another pair. Save yourself the trouble; read this guide, then go out and find yourself a decent pair of shoes.

Let’s hear it

I’m sure there are naysayers out there. Or maybe not, maybe you totally agree with me. What’s your take on spending top dollar for a nice pair of shoes? Let us know in the comments below.

PS, you should follow me on Twitter.

image credit: Ryan Plett


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25 Responses

  1. Rule on

    I have 2 pair of Bally dress shoes  ( back when Bally was a well made shoe  $125.00 then) that are over 30 years old. I have reheeled them etc etc and kept them polished  They are still looking good and feeling great.  Buy quality, take care of them.  Most important make sure they fit well as nothing is as bad as a good looking shoe but your feet hurt after 1 hour.

    • Barron on

      That’s amazing, you should share some photos of those shoes! Further proof that it’s always good to buy a great quality pair that fits well; they’ll last forever.

  2. Andrés on

    I had been drooling over a pair of Allen Edmond’s for a long time, I believe they were $295 at Nordstrom I believe. I’m a size 8 wide, so I never thought I would be able to find any good quality shoes at a thrift store or anything, but I decided to give Nordstrom’s Rack a try, and behold.. tucked way in the back in between basketball shoes and work boots, were a pair of Allen Edmond’s “Clifton” which was the exact shoe I was looking for, in a size 8 Wide, for $99. Still a pretty hefty price for an 18 year old, but I splurged and I do not regret it one bit. Quality wins this one for sure.

    • Anonymous on

      I bought my 1st pair of proper shoes (Allen Edmonds ‘Vernon’ Oxfords) a few years back. 

      I can never go back to disposable footwear.

    • Barron on

      Nordstrom Rack is a great resource. I’ve found plenty of shoes there. I wouldn’t be surprised if at 28 you’re still rocking those. As long as you take proper care of them (shoe trees, don’t wear them every day, resole them when you wear them down) you’ll have em forever.

  3. Richard Jackson on

    I, too have 2 pairs of Allen Edmond Park Avenue oxfords(12 yrs old) that have been re crafted using their mail in service. best $500 investment I made in my wardrobe. I used to buy Bostonian, Dexter and other brands in that price range, and I found that I wore out the sole and heel in less than a year so I was replacing shoes that cost $80-90 every year. The cheaper brands are glued together vs. sewn together, so when the heel and sole wear out they have to be replaced with another pair of shoes. Anyone that says $300 is too much for shoes, and you actually wear dress shoes daily for work, do the math, the numbers don’t lie.

  4. Felipe on

    Your mileage may vary… i bought a shoe from Richard’s a while back and bought thinking of quality, tried a bit, but it revealed to loose for my feet and one size less it was too tight… had another bad experience with a polo play shoe it simply desintegrated after some time… guess it took too much rain, so my fault also.
    Currently i only buy cheaper shoes.. sometimes they’re crap, but a few gems can be found.

    • Barron on

      Sounds like your experience had to do with choosing the wrong size, not necessarily the quality of the shoe. In that case I would’ve purchased from a different brand or a different model.

      Also, rain ≠ bad for shoes, unless you’re wearing rain boots. 🙂

  5. Josh M on

    I totally agree with this post. I purchased two pairs of shoes at about $100 each – a black pair and a brown pair. The black pair was a Florsheim on clearance and the second was an Express shoe at retail. Now, granted these aren’t by any means amazing shoes, but they are higher in the price range for my standard of living – just graduated, finally getting on my feet (hah).

    The Florsheim lasted 4yrs through grueling conditions on campus while trying to be fashion conscious and still light on my feet. I finally gave them up after the sole of the shoe was so thin, I could feel the bloody concrete.

    The Express shoe lasted not two months before the adhesive on both toe and heel gave way. The construction was very superficial and the material, although impressive at a distance, grade low in authenticity and even lower comfort.

    In essence, you get what you pay for. Drop trou and go with quality, because in 5years, a good shoe can still be revived by a seasoned cobbler.

    A cheap shoe won’t.

    • Barron on

      Hey Josh, thanks for your comment. Curious, what kind of Florsheims were they? I know some you can get resoled, but other models probably aren’t worth it.

      Express makes shoes?

  6. Soleful Strut on

    Any suggestions on another quality cap toe oxford (or similar) other than AE Park Avenues that are a comparable or lower price but similarly durable & comfortable?  I tried on a pair of Park Avenues, & while I can greatly appreciate the investment, I find they just look too old fashioned for me.  I saw a pair of Cole Haan Air Garrett cap toes right next to the Park Avenues that looked far more modern but still retained the aura of a classic style.  Are Cole Haan’s a worthwhile brand?

    • Nick B on

      Full disclosure, I work for Johnston & Murphy. But in the Value/Quality/Comfort equation, I have been a J&M fan far longer than I’ve been with the company. You should take a look at the Hutchins or Tyndals. They’re both more modern variants on a cap toe.

      • Soleful Strut on

         Thank you for the recommendation.  Any thoughts on the Suffolk Cap Toe?  They have a sleeker look to them that the others do not, IMO.  What is the life expectancy for such a pair?  I noticed the Hutchins are listed as being repairable, is the same true of the Suffolks or other J&M dress shoes?  Perhaps this is a foolish outlook, but I cannot see spending more than $125 for a disposable shoe when there are reasonably comfortable & attractive shoes for less at shoe outlets.

        • Nick B on

          The Suffolks are nice because they are crazy comfortable and waterproof. But the picture on the website makes them look a little dressier than they are in person. There are a bunch of shoes that can be recrafted, pretty much anything with a leather sole. However, the website only lists certain styles as recraftable by J&M. Otherwise take them to a competent cobbler. The life span of a shoe can vary wildly between different guys. As long as you follow some basics care instructions (shoe trees, alternate shoes every day etc.) you should expect to get years of use out of them.

        • Barron on

          Nick — thanks for swooping in and dropping some knowledge on J&M for us, appreciate that.

          I personally like the look of the Park Aves you were originally asking about, but I don’t have any firsthand experience with either this model or the Air Garretts, so I can’t speak to how they hold up long term. At least you have perspective from the J&M side now, though.

          • Wmalonei on

            I own 20 pairs of Allen Edmonds shoes. In a word ‘fantastic’. You need to spend at least $300-$500 for a quality pair of shoes. Keep them clean,polished and on shoe trees and they will last you a lifetime. You can go to the factory seconds store (Outlet) and get them as well. The cost of ownership will go down as the years go by. Second choice would be Aldens. Both American made and of the highest quality. Buy wisely my friend!!!

    • Nick B on

      Full disclosure, I work for Johnston & Murphy. But in the Value/Quality/Comfort equation, I have been a J&M fan far longer than I’ve been with the company. You should take a look at the Hutchins or Tyndals. They’re both more modern variants on a cap toe.

  7. Dave Hahn on

    Nice shoes are friggin’ indestructible too! I have a pair of Polo bluchers made in Italy that I got right out of college when I thought I’d be wearing suits to work every day. Well, I ended working in video post-production so I don’t have to dress nice at all (though I do) and just wore sneaks for a couple years before I decided to start dressing like an adult. Tried to find those shoes and one of them was lying in a pool of water next to my central air unit and looked fucked up! Moldy and gross looking in the heel. I thought they were fucked. Let them dry in the sun. A little discoloration in part of the heel but other than that tip top. Good shoes like any quality leather product gets better with age.

  8. Gazman on

    A lot of style bloggers bang on about the imperative of spending ‘at least $200-300’ on shoes and while I agree that one should focus on quality I reckon you can get quality without having to shell out anywhere near that astronomical amount. You just need to know what to look for and where to shop from. I have about 20 pairs of shoes in my closet and the most I have ever spent on one is $220 ( a pair of Ralph Laurens discounted from $600!). I have some decent brands among my ‘collection’ including a pair of black Bally dress shoes that I scored for $30 on eBay and a pair of Loakes that I got on deep discount. I’m wearing a pair of AEs as I write this comment, which I bought it on Ebay for $45. And here’s the thing: I wear a very small size (7) which is a bitch to find so anyone with more of an average size feet should not have too many problems. Apart from eBay, shop online, at thrift shops and wait until the big sales happen. By the way, I also own ‘lesser’ brands, shoes which I purchased for under $100 and they are fine by me. They are stylish and they last.

  9. asian_dapper on

    Nice article as always! I might be late to the party (of the commenters) but I still wanna say I’m in the process of rebuilding my lean wardrobe right now. I’ve been doing an IT job for close to 6 years now but I haven’t even thought of building an impressive wardrobe. It might be because in the first company (2 yrs) we have a short polo as uniform with a company logo. The second company I worked for requires long sleeved shirt and a tie, but even then the idea of having simple white and light blue dress shirts haven’t dawned on me. Here in my 3rd and current company, I’m seeing lots of guys wearing suits and nice dress shirts so I kinda figured out it is the time to change.

    I have lots of random long sleeved shirts in my closet, as well as more than normal pair of pants/chinos/trousers but I never owned a suit. Also, my leather shoes (although you can perfectly use them in the office and in no means causal) leaves alot to be desired.

    Fast forward now (about 6 months before I started dressing better) I now have 4 pairs of decent dress shoes. Black wingtip bluchers, black blucher captoe, brown blucher longwings and a brown double monkstrap. All of them have leather upppers but only the black captoe have all-leather sole. You see im still in the process and have a very long way to go.

    For dress shirts, I now have a very nice Simon Carter white dress shirt, some slim fit H&Ms in neutral colors (fits my athletic body well) and some random gingham and plaid shirts as well. All my dress pants now are hemmed to the right length and are all slim fitting.

    To close, I must say I’m very happy I found this site (and because it helped me tremendously with all the questions I have being a newbie in the world of building a magnificent wardrobe and at the same time, looking and feeling good.

    This article is also published the same date as my wedding, beat that! 🙂

  10. Christopher Barker on

    I love a good shoe as much as the next guy, But I’m curious…Is it really appropriate to spend more than 50 on a pair of shoes if you will only wear them maybe two or three times a month. Even an inexpensive shoe will last quite some time at that rate.