When to Say When

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This week I put my old Weejuns out to pasture. This is not easy for me as I don’t always know when to say when. I mean almost never. I am pretty sure that a lot of you out there can relate. There is a fine line between well-worn and over-due, but I seem to miss it quite often.
Old Weejuns I have been wearing my current pair of Weejuns for right around 3 years (see above). To some of you this may sound like no time at all and others an eternity. For the most part I am desk jockey so they don’t see much action outside of the walk from the parking lot to the office and back. I will be honest. While I don’t walk in them a ton I am very hard on my shoes. Monday through Thursday I rotate between two pair of Weejuns, but I end up wearing my brown pair 75% of the time. I also do not use shoe trees. I told you that I was going to be honest.
New WeejunsAfter reading the paragraph above I am sure it is clear to you that I needed new loafers (and better shoe-care habits!). It was clear to me that I probably needed new shoes, but if I had not found a new pair of Weejuns in my closet I doubt I would have made the leap.

This is actually where I could use some advice. What measurement if any do you use to know when a clothing item needs to be moved out of the starting line-up? This does not have to be limited to shoes. It could be for shirts, sweaters, trousers, sport coats, suits, etc. Please help a trad out!

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is a simple man interested in simple, classic, and traditional style.

17 Comments on "When to Say When"

  1. Joel Vau says:

    Jerrod, do you polish them? Does not look as if they have been. I think your old pair still has life in them. Also, as to your question: Pennies when they have worn spots which will no longer hold polish; OCBDs when the cufs are frayed; blue blazers when the elbows get shiny or the lapels are frayed; and khakis almost never, mine ususally get stained from working around the house and then they have to go.

  2. Alan says:

    As a trad wearer who does not follow the latest style, you should not have to replace your clothes as often as fad followers, if you take care of them. Just the basics, for goodness sakes. You use the right hangers for your jackets, so they will keep their shape? Do the same for shoes. You brush off and clean when needed your jackets, trousers and sweaters? Do the same for shoes. You repair jackets and trousers (missing buttons, pulled seams) so do the same for shoes and have them resoled, not just reheeled. And for goodness sakes, keep them polished. You can get away with the Boston cracked shoe look if you wish if you at least have a polish (Charlie’s Aldens aside, not a good example, I think.)

    If you want to wear down your casual clothes — worn collars on OCBDs, sweaters with loose neck seams and holes in the sleeves, fine, but going to work should call for a different standard.

    At least, that’s my opinion. If your clothes are important to you, treat them as though they were.

  3. Bluchermoc says:

    Those should definitely be resoled. Simply because they don’t make them like they used to anymore. Items get moved to casual wear from the work wardrobe when there is too much fraying going on.

  4. Charles Dana says:

    Sorry, Jerrod, but there’s no easy answer. Clothes don’t come with an expiration date. You just have to play it by ear. Some people always want to wear clothes that look fresh and new; others strongly value the patina and unique, well-worn slouchiness and softness of highly broken-in clothes. Most people are somewhere in the middle—and each person has to decide for himself where on that spectrum he is most comfortable. There is no one correct place. It also depends on the type of clothing involved: old casual garments look better than old dressy garments (with the exception of very high quality dress shoes—good shell shoes with an aged patina look good). Considering the casual clothes that you typically wear, I don’t think you need to worry about when to put anything out to pasture. Your inner voice will tell you when an item has gone beyond “comfortable and broken in” and has entered “ratty” territory. Of course, you could get married—then your wife will happily take it upon herself to tell you in no uncertain terms when it’s time to throw out a beloved garment. She might even dispose of some of your old clothes without telling you. How convenient that would be. But getting married might be a drastic solution to your dilemma. Kind of like getting rid of a tree stump by dropping a 500-pound bomb on it.

  5. R. Paternost says:

    The tops look perfectly good. It would be a shame not to have them re-soled.

  6. Lennart says:

    A piece of good advice. I had my latest pair resoled a week after buying them, now I had them for about two years and they still look good. Don’t use them daily, have a number of differrent pairs to altrnate with. Also polish, not too uber-shiny, certainly not on brown shoes… but they do need some polish now and then. However, I would say, where you are with your weejuns I am with my polo shirts, usually someone needs to tell me to stop wearing them :-)

  7. EC says:

    I am a high school school teacher. I use ten shirts and seven pants, with a couple odd ones peppered once or twice a month. My key for longevity has been rotation. I’ve clothes more than 15 years old that are common brands, Lands End, Dockers…. and they still hold their own. Rotate clothes just like shoes and you’ll be surprised how much longer they last.

  8. JJ says:

    Nice shoes but the soles have had it. Trads are faithful to Weejuns, but look into Allen Edmonds, particularly the Patriot. Closeout sales right now on that model. A vastly superior shoe to Weejuns. Also, get some shoes trees and polish. Your shoes will look better and last longer.

  9. Paper Clip says:

    One other suggestion is get a different sole put on them – like a commando or other rubber soul and use them for damp days…

  10. Fred Johnson says:

    I always get the Larson weejun which has the double leather soles, and get them resoled when necessary; my last pair are 5 years old. As previously said, good care and rotation are the keys to long life and low cost per wear.

  11. Pete says:

    Those look like they could be resoled/polished up by a professional cobbler. You might be surprised how they can breathe life into your stuff when it is starting to look a little (or a lot) worn out. I have a shoe guy that basically got three more winters out of a pair of Clark’s boots that I had, and they still have that nice, broken-in feel and patina to them. I work in commercial real estate in Detroit, and I beat the hell out of my stuff. From my experience, those shoes don’t look so bad. However, there is one part of the math problem here that is up to you. If those were a more expensive pair, like say Gucci, Allen Edmonds, or Alden’s, you would be crazy not to get them fixed up. Bass Weejuns though can be bought on sale at Macy’s in the $70.00s, so it might not be worth it to resole them.

  12. BRB says:

    First off, at a glance from the photos, those shoes have just come into prime.
    Yes, they need resoled, but aside from that, like a soft pair of khakis or OCBD, they are just beginning to come into their own.

    When it comes to shoes, the soles take the brunt of everything and while they may not show the first signs of a need for repair, they will be the first to require it…..and will do so many times over compared to the rest of the shoe.

    Sadly a dying art, but at least at this point in time, I imagine nearly every average size city can still claim at least one reputable cobbler. I must confess that the cost of such work has certainly increased over the years, but no less worth it when you are dealing with shoes that cost well above average….whether Weejuns still fall within that realm or not may be debatable, but may certainly still qualify for a round or two.

    The rest of the wear most likely can be marked down as cosmetic at best, and quite frankly, most preppies and trads should appreciate a more “been around the block and handed down a few times” appearance anyway.

    Crazy thoughts, perhaps, but, that’s coming from someone who resewed his 20 year old LL Bean Blucher Mocs, so I’ll let you be the judge of sanity here.

  13. oxford cloth button down says:

    Thanks for all of the great feedback here. It is appreciated!

    Lots of you are doing the cost/benefit analysis that I am. The nearest cobbler is about 35 miles away. It costs about $50. Weejuns can be had for about $75. Also, by putting out to pasture rest assured that I did not mean the trash can. They are just in my closet and may even get resoled!

  14. Charlottesville says:

    Glad you are thinking about re-soling them, Jerrod. Well worth the money. I also have to say that the new Weejuns that I see in the local stores do not look as good as the ones you have; most of the new leather looks like plastic. Yours pictured above look like good calfskin. I switched to Allen Edmonds a while back for this reason but admittedly, even on sale, they are a sizable step up in price.

    All of that being said, I have clothes that are decades old and still look great, and I have bought others that I had to toss in a year or two. However, actual holes in the cloth, ripped out seams, etc. are a bit too “traditional” for me. An exception, would be the fraying collars and cuffs on some old OCBDs and khakis, but even then I confine them to leisure hours. Good things tend to last longer, but eventually everything wears out.

  15. Andrew says:

    It appears that Weejuns are no longer available in B or Narrow widths. However, on the advice of JJ (above) I ordered from the Allen Edmonds shoebank.com website a pair of Patriot with size 9 1/2 with B width. They only had one color, brown, but will be fine if it fits.
    Why has it become so hard to find narrow shoes? Has there been an evolution to wider feet since I was born?

  16. Richard says:

    Another advantage to re-soling these shoes is that you’ll have 2 identical pairs of the shoe you like to wear the most, so you won’t favor one over the other and you’ll spread out the wearing evenly. I long ago decided it was worth investing in 2 identical pairs of tasseled loafers so I can wear my favorite shoe to work every day. Also, get some of Allen Edmonds’ leather lotion. It will add years to the life of your shoes and can be used in place of shoe polish if you prefer less shine.

  17. Gary says:

    Please do get the Weejuns resoled. They look brilliant and deserve to live longer. And few things can beat a broken in pair of loafers.

    And do not forget to post pictures once you have had them refurbished!

    Concerning your question about moving clothing out of the starting line-up, I feel it is always a shame
    to discard any item before it has completely fallen apart. Like in the Ivy Heyday, there is a certain desirable quality to an OCBD with a frayed collar. Think of all the poseurs who took sandpaper to their new shirts in an attempt to achieve the look. I personally use it as an indication to retire a well-worn and loved shirt from workwear to the off hours selection. There is a similar criteria for khakis, chinos, etc.

    And I have a wonderful feeling of satisfaction when an item of work clothing reaches this stage.

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