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Are $300 dress shoes worth the investment?

Q: “I recently read The Compass post, “How to a Build Your Dress Shoe Wardrobe“, and noticed that some of the dress shoes featured were over $300. That seems like a ridiculous amount of money to spend on a pair of shoes. Is it really worth spending that much on a pair of dress shoes?” – Joe H. 

A: While not always the case, a higher price tag on a pair of dress shoes will usually signal a higher quality of leather and construction. A well-crafted, high-quality pair of leather dress shoes is a long-term investment. With the proper care (cleaning, polishing, conditioning, using shoe trees, rotating wear and resoling), a pair of well-crafted dress shoes can last 20+ years (and in many cases, a lifetime). That said, $300 (or more) is still a lot of dough to drop on a pair of shoes, so let’s break down the long-term costs:

$300 at 20 years, with $10 worth of shoe care product per year and 6 resolings at $50 = $40 per year

When you compare that to the $1,000 the average American spends on coffee per year it doesn’t seem like quite so much!

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56 thoughts on “Are $300 dress shoes worth the investment?”

  1. sepatu pria says:

    Hi there, yes this paragraph is really pleasant and I have learned lot of things from it regarding blogging.


    1. Black Lapel says:

      We’re happy to have dropped this wisdom on you, now go drop some dough on those pair of shoes!

  2. Terence says:

    I finally ditched the square-toed, alligator, spectators. Had a funeral. LOL!

    Anyway, I don’t prefer a burnished shoe. Is this a good thing or bad thing? Because I believe it’s a fashion-forward look (a fad). But let me know what you think.

    Here’s to looking sharp,


    1. Black Lapel says:

      Bet you were dressed to kill at that funerl too, Terence!

      You may be right about the whole burnished toe thing. Of course, since a well made pair of shoes lasts a long time, the time frame of a “fad” is relative. You’ll probably be seeing them on well-shod men for another five or ten years before it’s time to give the burnished toe an official farewell.

  3. Terence says:

    I gave away 5 or 6 pairs of shoes in the last 6 months to make more room but there’s one pair I can’t seem to part with. Would you still wear alligator spectators that are squared-toed? They look great with 2 outfits I wear but those wide squared toes… I wonder. Do I look ridiculous but I’m deluded or what? My wife tells me to keep them but I might just part with them. What do you think? I still have 16 pairs and counting.

    1. Black Lapel says:

      Alligator spectators aren’t going to make our list of must-have shoes anytime soon but as a 16th pair of shoes, it’s not like you’re going to be wearing these shoes all the time. With that in mind, we say if you’ve got the space, go ahead and keep some spectators in the collection.

      That being said, spectators, with their high contrast look, call attention to themselves. So, if you’re looking to “get away with” some square toe shoes, these are not the ones to try to do it with. Why not replace the outdated square toes with a rounded-toe spectator that will never go out of style, like these beauties from Loake?

  4. Gabriel says:

    Can you suggest ways to tell whether a shoe is of good quality?

    Disregarding pricing (because i regularly see $300+ shoes with cemented soles and using polished leather AKA corrected grain) and the use of a goodyear welt.

    At the upper price levels it seems that it gets murky, how can you tell the difference between a $500+ shoe and a $300+ one? If you were to do a blind test (no brand logos, etc) with two pair of shoes, could you accurately guess which is of higher quality and why? Let’s assume a pair of Churchs vs Loake 1880s, both shoes made in England.

    I’ve often heard things like “finishing” and “quality of the leather” but when pressed for examples, people typically start stuttering, evade the question or tell me to go find out myself. That suggests that some people at least are hopping onto the bandwagon and just using buzzwords…

    Hard mode : How do you judge the quality of a shoe online, with only access to pictures?

    1. Black Lapel says:

      There are two things to focus on when judging the quality of a shoe, Gabriel. Aesthetics (an ugly shoe is an ugly shoe no matter how it’s made) and durability (will it hold up to wear and tear). The former is subjective, though we think all of the shoes in our piece on building your shoe wardrobe are damn good looking. As for durability, a Goodyear welt is a good indicator of how well a shoe will hold up. A Goodyear welt is virtually waterproof and makes the shoe extremely easy to maintain (resole) over the years, which makes for a durable shoe.

      Of course there are some well-made shoes that are NOT Goodyear welted, but it’s a good benchmark for a shoe that was made with quality craftsmanship in mind.

      1. Gabriel says:

        That’s odd, i’ve been told by a lot of people that leather soles, even when goodyear welted, do not work well in rain and are hardly water proof. Unless theres a intervening cork layer or something.

        What about the leather quality? Even if a shoe is advertised as full grain leather, there are different grades of full grain leather.

        This is mostly for comparing two classic goodyear welted shoes against each other. Both shoes are well made, but they are placed at different price points and one is supposedly much higher quality…but why? And how can you tell?

        1. Black Lapel says:

          To answer your question about leather soles, we like adding a sole guard to our leather soled shoes to avoid rain/water problems.

          As for leather quality now you’re getting a little deeper than information you can get from a website. As we said, price is a decent yardstick to determine shoe quality, but it’s not as simple as that. There are many factors that can lead to differences in price between similar quality products (varying production costs, marketing budgets, pricing strategies, labor costs, and shipping costs to name a few).

          The moral of the story: don’t take the price differences too literally, Gabriel. Go with the shoe that’s made to last, fits you well and you like the way it looks.

  5. Nathaniel says:

    I second the rack. I’ve picked up 3 pairs of allen edmonds there over the years and never paid more than $100 a pair. It costs more to recraft them than what I paid, which I just got done to my first buy after 5 years of wear. Good deal.

    1. Black Lapel says:

      And for Allen Edmonds in particular, there are often sales on the AE website as well.

  6. Rich says:

    Shop Nordstrom Rack. Their shoe stock is typically 50% of retail and is usually only there because it is a half season behind. Just picked up some very nice tan Cole Haan wingtips for $130…($275 original)…

    1. Black Lapel says:

      True, Rich, there are lower prices at the Rack and other similar discount and outlet stores. But, and this is a big but (we like big buts and we cannot lie), don’t be dazzled by the discount. As we said, a higher price often goes with quality leather and good construction, but a high price plus a deep discount can be a sign of a shoe that was overpriced to begin with. Look for quality.

      A telltale sign of a shoe that will stand the test of time is a Goodyear welt. These shoes can easily be resoled so they’re capable of going a good twenty years in your shoe rotation. Even at full price, as we showed above, these are often the best deal over time.

  7. Calvin says:

    What do you recommend for a man with small feet? I wear size 5 kid shoes. Size 6 men’s shoes don’t fit.

    1. Black Lapel says:

      We suggest talking to your cobbler first and coming up with a gameplan. A heel insert, for instance, may help make a size six work for you in certain brands that run small but only an expert, looking at your foot in-person, could tell you that for sure. As you know, going up to a six would open up an entire world of choices to you.

      If you don’t find a way to comfortably fit a size six, never fear, Shipton & Heneage offers several styles of their bench-made shoes in men’s size 5.5. These are well-crafted, great looking shoes you can invest in, so you could build your entire shoe wardrobe (if you need advice in that department we’re here for you) on these alone.

  8. Gabz says:

    We were more than happy to pay 200+ for sports shoes back in the day and how long did they last? Brands alone aren’t worth $300 but a quality made shoe is.

    1. Black Lapel says:

      Well stated, Gabz. Way to add a bit of perspective too with the reference to those Jordans we HAD to have back in the day.

  9. Gabriel says:

    Just get some $100 shoes . . . it’s all the same, for god’s sake!

    1. Black Lapel says:

      That’s like saying Pop Warner and the NFL are the same. Yeah, they’re both football but there is a difference in quality, no?

      It’s your choice, but we’ll take well-made shoes that last forever and can be kept like new for years any day of the week.

  10. Terence says:

    I guess I better not mention what I pay for shoes because someone who thinks $300 is money for shoes, then that person will think I’m insane. However, no fine dresser can be completely dressed with terrible shoes. Suit yourself.

    1. Black Lapel says:

      “No fine dresser can be completely dressed with terrible shoes.” Well said, T.

      There are deals to be had out there, gents, but always keep quality as the main objective, when it comes to shoes, and you will be well shod for years to come.

  11. Joe says:

    For the record: I have a pair of J&M moc toe shoes that are 25 years old that I paid close to $200 back then. That was a good piece of change 20 yrs ago however I knew they’d last. They’re an unusually thick leather with seriously robust stitching. They have been resoled once and their life has benefited by a dozen pairs or so I rotate. When the more square toed shoes were happening the moc toes got shelved for a short time. I’m old enough to have seen styles come and go more than once and I knew I’d wear them again. And probably MOST important to me is that quality shoes are much better for your feet.

    1. Black Lapel says:

      Your relationship with these shoes has lasted longer than many marriages, Joe! This is a great example of how a great pair of shoes are well worth the investment.

  12. DK says:

    Hi, it’s not really related but I was wondering on the colour matches for shoes and suits/bottoms. Like for example I’ve read that brown shoes should never be worn with a charcoal suit? If there was already a post about this I might have missed it

    1. Black Lapel says:

      Gray and brown makes for a great combination, DK. Black is an easy combo with gray, but we like brown with a Charcoal Gray suit to add a little richness to our look (that’s “richness” as in “having a pleasantly deep and strong color,” though a fat wad of cash is not the worst accessory we can think of). One caveat is to keep the brown shoes dark if you’re wearing them with a dark gray.

      We didn’t talk matching specifically, but we did do a piece on building a shoe wardrobe (which is now linked above).

  13. Paul Evans says:

    $300 dress shoes are absolutely worth the investment. I’ve spent significantly more on shoes (i.e., John Lobb) knowing full well I will have them for 10+ years. Make sure you are buying a quality pair of shoes, take care of them and they will last you.

    1. Black Lapel says:

      Preach that gospel, Paul!

      When you spend on a good pair of shoes you’re naturally inclined take better care of them because you want to justify the expense. The whole thing becomes a virtuous circle.

  14. Kevin Sonntag says:

    You’d be surprised at the quality of some of these shoes after a long period of time. I managed to grab some old (circ. 1980s) Johnston & Murphy tassel loafers at Goodwill for $7. All they needed was a good oil/polish treatment and they look brand new. My father even still has his J&M dress shoes from the 70s. I recently spent around $300 on a pair of Allen Edmunds cap-toes that I plan on keeping for quite some time. I read in another article that if you’re wearing a suit, the shoes should cost just as much if not more.

    1. Black Lapel says:

      There’s a reason for the phrase “tough as leather. Take care of your shoes and they’ll take care of you…for a long, long time.

  15. Tyler Alder says:

    I realize that budgets and priorities vary, but $300 is hardly a lot of money for a shoe. Allen Edmonds is generally considered to be the entry level of quality shoes and most of their models start around $350. True quality shoes from the traditional English makers are generally upwards of $1000. This may seem like a lot of money to some but, as others have pointed out, quality shoes last decades (even a lifetime) when properly cared for. Additionally they will never go out of style and they will look better and better with age as the full grain leather develops a patina. The corrected grain leather used in lower quality shoes only looks worse with age.

    1. Black Lapel says:

      Very true, Tyler! In other words, a fine pair of dress shoes are one of the few items in your wardrobe that can actually appreciate in “value” over the long term!

  16. Zamri says:

    Shoes are very important to one’s wardrobe because they anchor everything down. Having bad shoes not only will cause the leg pain (blisters, bunions, etc) it could ‘destroy’ the style too. I had quite many shoes above $300 price tag, as well as those from highstreet. To be honest, the pricier shoes are truly worth the investment. They last longer and aged better with time. The material is of high quality – if it’s leather, high-end shoes uses best leather compared to highstreet, as they’re much softer and supple and doesn’t ‘bite’ the foot. I’ve been wearing the high-end shoes for the past 5 years, and it still feel amazing despite the sole has worn out.

    1. Black Lapel says:

      You bring up a lot of good points, Zamri, especially about how your better shoes age. Good shoes are like fine wine and Denzel Washington, they age well.

  17. Yesman says:

    I live in Norway. Forgot to write that down.

  18. Yesman says:

    I have just started to go in a more classic style for everyday. Have bought blazers in blue and gray colors, both in wool. Do you have any suggestions for some blazers that fit in the summer. I do not know what to buy on. I have five shirts. six chinos in blue, beige, olive. Also Shorts in white, blue and red. Have some sweaters in black, blue and gray. Also classic shoes in brown leather, but do not know what to buy to get a better look.

    1. Black Lapel says:

      Looking at the pieces in your wardrobe, both our French Blue Check Blazer and Solid Tan Tropical Wool Blazer could make for great summer blazer options.

  19. Anish Patel says:

    FYI, I paid £250 for those, approx $400, and these are my daily work shoes and have been for the last 5 years.

  20. Anish Patel says:

    I bought myself a pair of Church shoes when I started working in 2008 and they’re still going strong. Not only do they still look great, they now feel like the most comfortable shoes I’ve ever owned.

    1. Black Lapel says:

      Agreed, a pair of Church’s are a fine investment. They make exceptional shoes that are known to last decades when properly taken care of.

  21. Yves says:

    I was going to buy a new Black Lapel suit, but I might as well purchase new dress shoes first 😉

    1. Black Lapel says:

      The dress shoes are only as good as the suit you wear it with. 😉

  22. Brandon says:

    If you’re buying a pair of dress shoes (at any cost) that will be dated in a few years, you’re doing it wrong. Dress shoes should be timeless; that’s the difference between style and fashion.

    With that said, if you only plan on wearing them two or three times a year… well then, buy a cheap pair in a classic style. Investing in quality is great, but after only a dozen wears a pair of $80 shoes will hold up as well as a pair of $300 shoes. It’s all about cost per wear.

    You can still get high-quality shoes for cheap, though. I have four pairs of dress shoes. Black and dark brown cap-toe oxfords, burgundy shell cordovan wingtips, and a pair of walnut monk straps. All are Allen Edmonds and all in great shape. I bought each of them them on eBay and have spent about $250 on the four pairs combined, including shipping.

  23. Jovan says:

    Black Lapel, you get major props for espousing traditional shoe styles and an investment in quality.

    I’ve seen some guys trotting about in shoes that are 5, 10, and even 20 years old and not looking dated. Some of the severely chiseled or narrow/pointy styles are going to date badly, however, and I’m not sure why some men are buying these at Edward Green prices.

    I’m not sure why those damn square toed shoes are still around. They’ve more or less been preying on the style ignorant since 1999. I suppose they’re this generation’s Beatle boots?

    1. Black Lapel says:

      Jovan, we knew you’d appreciate the last few posts. 🙂 As for those square toed shoes, they’re around to make gents like yourself look better!

  24. Yes, absolutely 100% it is worth it. The quality and construction is SO much better when you are willing to spend over $300. Obviously you shouldn’t buy expensive shoes just because they are expensive, but there is no question that you get what you pay for.

    1. Black Lapel says:

      Nothing but the truth!

  25. apc says:

    I would not want to wear any pair of shoes more than 5 years, let alone 20, so in my opinion $300 is too steep a price to pay for them. In my opinion $200 would be the most I’d pay for a good pair.

    1. Black Lapel says:

      APC, if you can get a $300+ quality shoe for $200, all the power to you! 🙂

  26. Justin Brown says:

    Is there a limit to the number of times a shoe can be resoled?

    1. Black Lapel says:

      It really depends on the shoe and how they’re cared for. We recommend checking with the manufacturer as it’ll be different for every shoe.

      1. John says:

        Allen Edmonds says that recraftable shoes can typically be done twice. BTW, not all shoes are recraftable. BL hit the nail on the head, having a few different pairs that can be rotated will not only help the shoes last (not to mention you will have another pair or two to wear while getting heels replaced).

        1. Black Lapel says:

          You’ve got it, John, rotational wear (not wearing the same shoes two days in a row) really helps your shoes last.

          Another tip, taps on the heels will extend the life of the heel, especially for those who have what is known as supination of the foot (people who walk on the outside of their heels).

          The upshot is, take care of your shoes and they’ll take care of you.

  27. Tsn says:

    I don’t think I ever saw someone with a 20 years dress shoes?
    Wouldn’t the dress shoes will be out of style by year 5?

    1. Black Lapel says:

      It doesn’t get more timeless than a classic pair of brogues or cap-toe oxfords. Now, if you’re talking about black square-toed dress shoes on the other hand…

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