Singing the Thrift Store Blues

Bostonian Crown Windsor Tassels

I recently came across a shoe that on the second-hand market that I have been pining over for a long time. This shoe is none other than the cordovan tassel loafer. The only problem was one that all of my thrifters, Ebay scourers, and other experts of the second-hand/vintage clothing markets can relate. Will they fit?
Tassel LoafersCrown WindsorsThis specific pair of tassels are Crown Windsors made by Bostonian. These tassels are not from the current iteration of Bostonian, but rather from an era when their quality was on par with Allen Edmonds and Alden. This specific pair was being advertised as having not been worn outside, but after taking a close look at the sellers pics I believed them to be new old stock (NOS). The quality, condition, and price (when compared with a new a pair) made them very very attractive to me.

My first move was to do some due diligence. I contacted a man of many tassels that I know and sought his counsel. He could not provide me with any fit information in regard to vintage Bostonian tassels, but he did have other pairs of vintage Bostonians and sent me what info he had. I did some more research on the web and in the end I felt the odds were in my favor. I pulled the trigger.
Genuine Shell CordovanBostonian Crown WindsorWhen the shoes arrived they were in spectacular condition. I now fully believe that they have never been worn before at all, inside or outside. I was enamored, but the moment of truth was here. Try on time. They fit a tad big, but I was still hopeful that after a full day of breaking them in that they would work for me. I was wrong. They slipped all day and were even painful. I was and still am crushed.

This sad story is one that I know many of you have experienced. It is also why I am weary of the second-hand/vintage market. While I can certainly get my money back out of them it involves me reselling them which in my opinion is a form of torture. Moving forward I will be purchasing less and less from this market as I can afford it, but for now I will just sing you my thrift store blues.

oxford cloth button down
is a simple man interested in simple, classic, and traditional style.

21 Comments on "Singing the Thrift Store Blues"

  1. mhj says:

    You might try Dr. Scholl’s Gel Foam Insoles, they might just fill them in enough to make them more comfortable. Any big box drugstore should have them.

  2. lin says:

    It seems like there should be a way to make them fit!

  3. JT says:

    What size are they? I might be interested.

  4. Fading Fast says:

    I had the same thought at mho – it has worked for me. Also, tongue pads and moleskin on the back inside can help – the tongue pad (I used two per shoes in one case) has saved me from having to give up on several pairs of new shoes. Try all of this before you give up. I’m rooting that it will work. The shoes look beautiful.

  5. Fading Fast says:

    To clarify – the tongue pad goes under the tongue of the shoe and, separately, you use moleskin (with one side that is sticky) on the back inside of the shoe. Some combination of the foam insoles (go to the drug store and look at all the Dr Scholl options as you might – depending on where the shoe is most big – find one or several things to try), tongue pads and moleskins have a good shot at bringing the shoes down a half size and making them work for you.

  6. David says:

    what size are they?

  7. oxford cloth button down says:

    For those that are inquiring they are an 8 C/A.

  8. Allen P. says:

    Yes a little to big. I see in the picture.
    Nice effect from the colour of the shoes and navy blue socks.
    Try to use insoles to continue wear them.

  9. Fading Fast says:

    Hi, looking closely at the picture, the double tongue pad (two tongue pads stuck on the underside of the tongue of each shoe) might be very effective as it has helped me when I’ve had shoes that fit like yours do. Of course, that plus the others suggestions – Dr. Sholls, moleskin – might all be needed, but do it incrementally – start with the tongue pads would be my suggestion. Let us know how it works – good luck.

  10. oxford cloth button down says:

    Thanks for all of the tips gentlemen. I am still on the fence about rigging them to work. My money is probably better spent finding shoes that actually fit, but…

  11. Fading Fast says:

    OCBD, you can try the tongue pads without sticking them to the underside first – just keep the plastic backing where the sticky stuff is on and slide them in to place and see if that helps. You can do the same with the Dr. Scholls and moleskin. This way, if they don’t help, you haven’t hurt the resale of the shoe (and the stuff doesn’t cost that much and can be used on other shoes). I just really want to see these great shoes work out for you.

  12. Flo says:

    Your problem is something I’m all too familiar with. I’ve come to the conclusion that while a lot of clothing/shoes end up in thrift stores because of closet clean outs, anything that is relatively new or with tags still on is usually a fit issue. I’ve acquired a lot of pants this way, the favorite being a pair of Lands End pants that were the right size except they were petites. I decided to take a chance on them and was glad I did. I’m 5’6″ tall with long legs and they fit perfectly, obviously a sizing error and whoever had them didn’t want to be bothered to send them back. I’ve had a couple of misses but for the most part, I’ve had more good purchases and will continue to look at second hand clothing. Don’t give up!

  13. Steve says:

    I would echo the sentiments expressed already, that is, get a pair of inexpensive store brand insoles (I prefer them over gel by the way) and try them that way…I think you’ll be pleasantly surprised. This method is easier with oxfords/bluchers but can work with loafers.
    Good luck!

  14. Walter Denton says:

    I’m not sure I have ever had even a new pair of shoes that fit well out of the box. My feet are very wide at the toe and very narrow at the heel. Somewhere there is probably a last that works but I haven’t found it yet. I rely on gel soles and pads in all my shoes. Buying pre-owned shoes online makes it even more of a gamble.

  15. oxford cloth button down says:

    Walter – I can relate about shoes rarely fitting well, because of the similar issues. Your words make me feel better about trying tongue pads.Thanks.

  16. M Arthur says:

    What a great find! Fading Fast has provided great advice, but I lean towards the view that if you have to use a variety of support products to make for a good fit, get a different pair of shoes.

  17. lin says:

    It sounds like you need to try to make them fit & let us know how it goes

  18. Fading Fast says:

    I absolutely agree with M Arthur if they were new shoes from a store – but for NOS / great vintage find, it might be worth trying all the machinations suggested. It all comes down to how much you want them. I will not wear shoes that hurt my feet (period, full stop). But I have found that by doing some of the things suggested and wearing them a few times to let it all settle in, I have made shoes that I never thought would work be comfortable (because, again, I won’t wear them if they hurt my feet).

    So it all comes down to how much you want these particular shoes. If they aren’t that important to you – M Arthur is spot on.

  19. GusMom says:

    Do not get rid of them. Call a cobbler…see if they can do something….please. Inserts sometimes work…chunky socks?

  20. Ensiferous says:

    OCBD, I am disappointed that those great looking tassel loafers didn’t work out for you. I hope that this setback won’t keep you from trying again. As you know, it takes time, experience and money to get a baseline for fit on many different things.

    Buying shoes remotely on hope alone is best for those with at least somewhat of a gambler’s mentality. Sometimes winning, sometimes not. I think dollar-cost-averaging makes the bad deals seem less painful in the end, but it makes the great deals a bit more expensive. But once you know your size(s) in different makers shoes, the hope method can be replaced with the confidence.

  21. Andy Gilchrist says:

    When I was in college I once wore three pairs of socks trying to make a pair of longwings fit. Needless to say I sufferred from extremely sweaty feet and decided to donate them to charity. Jerrod, I strongly recommend letting these ones go…

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