54 Comments.

Hey gents,

I talk a lot about brown dress shoes… a lot. I’m a big fan of them over your typical black pair (because black is mostly uninteresting, unless you find the right pair).

On top of that, guys default to black dress shoes. Guys need to stop settling for “default” choices and saying to themselves, “Meh, good enough.” It’s important to be a little daring, step out of your comfort zone, and do things the rest of your peers are not doing.

So brown leather dress shoes are a step in the right direction.

But, to those still stepping up their game, what constitutes a GOOD pair of brown leather dress shoes? Can you just pick any pair that looks brown, and looks leathery? What qualifies as the RIGHT pair of brown shoes?

Well, what better way to explain than with pictures, am I right?

The WRONG pair of brown “dress shoes”

Here’s what you’re looking for… so you can avoid them. I say “dress shoes” because these aren’t really what I had in mind when I told you to go out and get a great pair of shoes.

I only pointed out a few things here, but you get the general idea. If you see any of these elements on a pair of shoes you’re considering, it’s best to back away slowly, turn around, and run.

The RIGHT pair of brown leather dress shoes

And here’s a good example of the kind of brown leather dress shoes you should look for when purchasing your first (or second, or third) pair.

These are the Fifth Avenue model by Allen Edmonds via Zappos. The characteristics I pointed out above are what you want to look for the next time you’re on the hunt.

Things like a narrow, sexy silhouette, leather upper and outsole, classic stitching, broguing (if you like it, i certainly do), the right heel height, and a Goodyear welt (the top-notch hand sewn construction, attaching the sole to the upper part of the shoe).

This particular model (and shoe brand) is expensive, sure. Not everyone can afford $325 shoes. But if you were going to own one pair for years and years, Allen Edmonds is one of the brands you want to explore.

Not only are they of extreme quality, they look damn sexy, they’re made in the US, and they even offer a recrafting service for all their shoes. For a fraction of the cost of a new pair, you can send your AEs in and have them resoled and cleaned up. After a few weeks, you’ll get your shoes back, looking better than ever.

Why not just buy a new pair? Because things look better with age, if they’re built to age well. Most cheap shoes aren’t meant to be worn years and years. Shoes like Allen Edmonds are (that’s why they offer a recrafting service in the first place… I’ve seen pairs that are 20+ years old looking as good as ever).

Plus, here at EG, we’re all about identifying and shopping for quality items, things that last, and using them for years. Why buy a $50 pair of “dress shoes” that last one year before the sole comes unglued and the “leather” starts to flake, rendering them completely unwearable?

This applies to dress shoes at any price point

But hey, I still hear ya. Even I can’t plop down four bills every time I want a nice pair of shoes. If this sounds like you, trust me, this isn’t about always spending top dollar.

The important takeaway from this is to look for these specific characteristics when you’re out buying shoes. Stay away from the WRONG pairs, and find shoes that resemble the RIGHT pair.

Boom! That’s it.

Questions?

Unsure about certain parts of the right pair, or why a certain wrong pair are wrong? Let’s hear it in the comments below.

 

ps — crazy, EG is almost at 1000 likes on Facebook! When did that happen? If you want to help us reach 1000 (not that numbers matter, but it’s just kinda cool to see), like us on Facebook here.

The benefit to you is that when we have a bigger community on FB, we can get into more detailed discussions about things and field opinions and thoughts from everyone else in the community. Plus, the conversation is better on there (and it’s easy to reach me). So like EG!

 

 

photos via zappos

PUBLISHED January 19, 2012


Barron is the Founding Editor of Effortless Gent and the Cladright Association. He's from San Francisco but currently living in New York. Connect with him on Twitter, Facebook, Instagram, or Tumblr.



  • http://www.jessydiamond.com Jessy Diamond

    Sadly, most of the dress shoes I see around here are in the “wrong” category. And the few decent shoes I can find are usually not available in my size.

    • http://effortlessgent.com Barron

      The internetz, my man! With return/exchange policies like Zappos / Endless have, you can’t go wrong with shopping on there.

      • http://www.jessydiamond.com Jessy Diamond

        I’m in Canada, so it’s a bit trickier. I can’t even order from Zappos.

        • http://effortlessgent.com Barron

          That’s a bummer, sorry to hear that. I’m sure there are other resources out there; I’ll keep you in mind if I find any.

          • http://www.jessydiamond.com Jessy Diamond

            Thanks, this is appreciated. And keep in mind I’m a size 6 to 6.5, just to make things even more difficult.

  • Daniel Isaacs

    Love this post. I just pulled out an old pair of Johnston & Murphy cap toes that look very similar to the AEs in your post. I bought them in the late 90s but never wore them very much (weddings, job interviews, etc.), kept cedar shoe trees in them, and they still look just a few months old. An added bonus is that they were made in the U.S. (not all J&Ms are these days, if any). To me, it was a reminder of how classic styles are always appropriate.

    • http://effortlessgent.com Barron

      Awesome. I too love how classic styles are just as relevant today as they were when you first bought them, even if that was years and years ago.

  • Peter

    What do you think about Florsheim shoes? They have a few styles that look like the AE’s you mentioned.

    • http://effortlessgent.com Barron

      Love em. I own a pair of Veblens that are practically my daily go-tos.

      Johnston&Murphy, Cole Haan, Bostonian, all somewhat lower price points, so worth checking out. I can’t wholly endorse all models… every brand seems to carry a few that fall into the No category. But sure, if the style looks similar to these AEs, you’re probably good to go.

  • KPS
    • http://effortlessgent.com Barron

      Those are awesome. I have a pair of Florsheim Veblen in the wine color, which is my almost-daily wearer. If you’re thinking about getting em, go for it.

  • http://www.facebook.com/profile.php?id=1265053572 Dustin Moskowitz

    Spot on with the AE’s. I’ve owned two pairs – one black, one chili – for a dozen years. They don’t get much wear, but they are incredibly well constructed and work with everything. I think mine were $250 at Nordstrom’s when I got them, and worth every penny. Pretty much exactly the Fifth Avenue model you showed, and I’ve never gone wrong with them. Great pick!

    • http://effortlessgent.com Barron

      I love hearing stories like this, because it just continues to prove the point that when your base style is classic, you’ll never have to replace these things (because they’ll always be current). The chili color sounds interesting, any photos or links?

  • http://twitter.com/Arkhangael Angel

    i have come across pictures of some brown shoes in a french magazine. it was like seeing shoes made in heaven..
    unbelievably beautiful
    i’ll come back if the manufacturer(s) have websites.
    i am a big fan of brown shoes, but brown shoes need to be perfect.

    • http://effortlessgent.com Barron

      definitely, please share the links if you find them.

  • http://www.facebook.com/profile.php?id=727411911 Drew Conway

    So I have to ask because I own a pair of brown “dress” shoes that look like the top left one: Are those the Ecco Windsor slip-ons?  And is that shoe considered to have a slight square toe?

    I bought those–fortunately used and at a much lower price point than the retail $230–before I discovered the world of cap-toes, brogues, Allen Edmonds, and all that :)

    • http://effortlessgent.com Barron

      I’m not sure what the exact model is; I didn’t take notes when I pulled the images. But that shoe does have a slight square toe since it’s not completely rounded. The unnecessary decorative stitching I pointed out accentuates it further. On top of that I don’t like the elastic at the opening.

      That model isn’t terrible though, the other ones are much worse.

      I still have some of my old pairs of “brown dress shoes” before I learned better; if I were at home I would’ve taken photos of those and used them as examples instead. They were beyond terrible.

  • Guest
    • http://effortlessgent.com Barron

      Thumbs up. They look a little long; not sure if it’s because of the size they used to do the product shots or not. Try them on to make sure they don’t look weird on you.

      Overall styling and proportions are good though.

  • Tpaciello

    agree with you 100%.  Have 2 pairs of all leather Cole Haans that were over $200 a pair but they are my best looking and most comfortable shoes.  I get new soles and heels about every two years and they are brand new again.  Don’t buy disposable cheap shoes.  It is a waste of money and people notice you are a poser.  Start dressing from the ground up.

  • Rob

    How do 6″ boots fair when you’re aiming for this? I just picked up a pair of Red Wing Iron Rangers (8111’s) for casual wear – largely for the quality concerns mentioned above – and I don’t have a lot of situations that demand formal dress. I wonder if they fit the bill for anything more than casual wear, or if I should keep looking for dress shoes. Full Disclosure: I do live in Texas, so boots are pretty much par for the (obnoxiously dusty) course here.

    • http://effortlessgent.com Barron

      If you don’t find yourself in dressed up situations often, then maybe you don’t need a pair. But, even on those rare occasions you do get fancy, don’t you want to look good and have the appropriate shoes on your feet?

      I love the Red Wings, and yes they’re great for everyday wear, but not in this context when we’re talking about dress shoes.

      I say pick up a pair of the right kind of dress shoes, and you most likely will never have to buy another pair again.

      • Anonymous

        That being said, I have the Iron Rangers and they can be dressed up quite well. To a point. At most, casual blazer, tie, and dark jeans. Or the sweater dress shirt combo. Like Barron says, a formal dress shoe is a must, but those Red Wings are bomb in a ton of contexts.

        Also, nice article Barron. I’ve been reading EG for awhile but first time poster.

        • http://effortlessgent.com Barron

          Hey Greg,

          Thanks for the comment (1st time! woo!) I agree the Iron Rangers are a nice boot and you can dress them up really nicely, with the outfit you specified (or something similar).

          If we’re talking about a legit dress shoe though, then yeah, the Red Wings wouldn’t cut it. Awesome in every other situation though.

  • Wmalonei

    AE ‘s are the best American made shoes for a man of modest means. Sure $350 is a lot for a pair of shoes. You only have to buy them once. They will last you a lifetime. How many $100 pairs will you buy in your life? I currently own about 20 pair(mostly from outlets) and they are as well made as Aldens,Edward Green or Graziano&Girling to name a few. Your wardrobe is an investment. Go classic. Buy good quality once and wear forever.

    • http://effortlessgent.com Barron

      Nice, I’d love to see that collection. Sounds pretty extensive!

      You ever check out Leathersoul.com? Lots of shoe porn for the enthusiast, and the brick+mortar stores look beautiful. Site’s great too.

  • http://www.indochino-review.com Lorenz

    Good points, especially the square toes are a design from hell…325$ may not be cheap, but in the end, investing in proper shoes pays off. Plus, as you said you can always have them refurbished.

  • Frank

    Hey  I just wanted to extend my gratitude for your advice. I had been wanting some dress shoes for a little while now but as a young guy I was intimidated by all of the choices. I also was probably going to buy a few inexpensive shoe but I eventually went for it and treated myself to a pair that was more than I would have spent normally. I could not be happier with my Johnston and Murphy Suffolk cap toes. Nothing ornate, nothing flashy, just elegant classic brown shoes that will last me a long time. On top of everything they don’t feel like medieval torture devices, like so many of my other cheap oxfords felt like, and I am glad to wear them.

    • http://effortlessgent.com Barron

      Hey Frank,

      Glad to hear the article helped, and that you chose a great shoe. J&M has more than a few good choices, and with a simple unadorned cap toe, you can’t go wrong.

      Nice work!

  • BC

    Hi, I just want to say thank you for this article, it helped me me a lot as I was searching for weeks for my first brown dress shoes. Most of the good ones are expensive, but finally I got mine, so thank you! 

    • http://effortlessgent.com Barron

      great! glad to hear it helped.

  • NY

    What’s your take on the AE’s in walnut versus the darker brown? I tried the walnuts on in person and they look CRAZY GOOD, but I’m not sure if they’d be too loud for a basic go-to shoe. I’d mostly be wearing them to work with grey or navy pants of varying shades, and occasionally dark jeans.

    • http://effortlessgent.com Barron

      I love the tan / walnut leather color for shoes. I have 3 pairs in different styles, all walnut, so I’m probably biased. They look great with grey, navy, and dark denim, so I’d definitely get those.

      I feel like I have to suggest dark brown here on EG most of the time, because some guys may be uncomfortable w/ walnut and lighter leather colors. But if you tried them on and you love them, buy em. They’re my personal favorite.

      • NY

        Rock out. Thanks.

  • Nategates
    • http://effortlessgent.com Barron

      I’m personally not a fan of saddle shoes, but I like how those are all one color (as opposed to the usual contrast style), and I’ve seen them pulled off well, so yeah if you like the style, I’d give it a thumbs-up.

      Those have a rubber sole by the way (great for slippery conditions, tip-toeing up behind rivals / enemies) but I prefer leather soles. Then again, preference.

  • http://www.facebook.com/people/Kevin-Ragsdale/100000021709429 Kevin Ragsdale

    I’m just starting down this journey.  I’m 42, and just sort of woke up  last week and realized “I’ve got to make a change”.  So, I’ve been busily reading Dappered, EG, The Style Blogger, and so on.  I’ve got my initial list of items and budget setup.  For shoes, I’m leaning towards Cole Haan Air Coltons.  They have a spectator version – 
    http://www.colehaan.com/colehaan/catalog/product.jsp?catId=100&productId=396272.  What do you think of a shoe like this?  I’m just drawn to the two-tone…

    This site has been an inspiration for me, and thanks again for a super site.

    • http://effortlessgent.com Barron

      Hey Kevin,

      That link doesn’t work, but as far as spectators go, I like them when they’re more tonal than overly-contrasty. That’s just me though. If you like them, I say go for them, whatever color they are. They’re a classic shoe.

      Thanks for reading!

      • http://www.facebook.com/people/Kevin-Ragsdale/100000021709429 Kevin Ragsdale

        Hi Barron,

        I can click the link from the post, so not sure what happened.  They are a light brown,  with a beige contrast. I’m going to grab a set, I think.

        Thanks again!

        • http://effortlessgent.com Barron

          Oh what, that’s strange. It didn’t work for me the first time around. Did now though.

          I like those. But, if they’re your ONLY pair of brown shoes, you’ll have a hard time wearing them with everything.

          I say get em, but be prepared to need a basic brown pair as well (something similar to what I pointed out in the article).

  • King

    Nice read! I’ve actually been meaning to get my first pair, but I’ve always had difficulty finding something that I would like, until I found these http://www.massimodutti.com/webapp/wcs/stores/servlet/product/duttiph/en/30259451/220507/814006/JUTE%2BBLUCHER 

    However I’m not sure if it would be wise to get a pair of leather shoes from a fashion brand like Massimo Dutti (wc is priced at about $100). Mind giving your two cents? 

    • http://effortlessgent.com Barron

      I’m sure they’re a decent everyday pair. Quality-wise, they won’t last and last and last, but you’ll get a few years (hopefully) out of them.

      If you’re okay with that, then go for it. Or, since they’re part of the huge fast fashion company Inditex, just wait till they go on sale. Eventually they will.

  • Ben

    What are your thoughts on these Barron? are they considered square toe?

    http://www.florsheim.com/shop/style/12031-200.html

    • http://effortlessgent.com Barron

      You’re cutting it close with those. I think it’s a good looking shoe and they’re being more fashion forward by shaping the sole that way. The actual toe box is still rounded, so it’s not really a square toe. I won’t hate you if you wear them, put it that way.

  • OIG

    Hi Barron! Just read GYS a month ago and I’ve been busy reshaping my style. Thanks for all your help!

    I’m not sure why in the Philippines, oxfords are unpopular. So I just bought a derby-styled Florsheim shoes (couldn’t find the model). OK for an all-around brown dress shoes?

  • Tj Shepherd

    My brown Florsheim shoes have finally been retired, and I recently stumbled upon these. What is your opinion on the brogue styling/tall boot combination?

    http://www.wolverine.com/US/en-US/Product.mvc.aspx/29387M/0/Mens/Winchester-1000-Mile-Brogue-Boot?dimensions=0

  • Peter

    Hi Barron,

    Bought a pair of Steve Madden’s for $140. They put my Aldo branded dress shoes to shame(wasn’t aware of a quality shoe then). Do you think they are overpriced or overrated at all? Any thoughts? Thanks

    Peter

  • Mike

    I am curious how long it should take a pair of Allen Edmonds 5th Ave shoes to break in. I just bought a pair and the leather sole seems stiff compared to the johnston and murphy rubber soled shoes that I have been wearing for a couple years. Will the leather sole eventually give me the same ground feel as the rubber soles? Trying to decide on keeping the shoes vs returning. Thanks for the great articles.

    • Joseph Wayne Frasier

      The breaking in process of an Allen Edmonds usually will depend on how often you wear it. My Neumoks broke in after about 10 wears, each consisting of 3-9 hrs. My Strands are the Brooks brothers model and have the cushioned footbed so they are altogether very comfortable. They will loosen up with time and wear but are definitely much better than any Johnston and Murphy shoe in both quality and comfort. Be patient and you will be rewarded.

  • Jay

    What’s your opinion on black + brown dress shoes? (roughly 60% black) Do they work well together or should they not be mixed?

    • http://effortlessgent.com Barron

      what do they look like? I personally like black and brown together, despite what people might think about it. it’s all in the way it’s put together. same goes for the shoe you’re describing.

  • Steve

    What is your opinion on brown shoes with a charcoal suit? What shade of brown should I be looking for?

  • The Elf

    Meh – I do like brown shoes but Ive never been convinced the classic wing tip semi brogue narrow toe box lace up is the key game in town. I ‘default’ to suede ankle boots very time. Im hoping one day I can roll with a handmade Chelsea boot with anatomically correct footbed, wide toe box etc. Those yawnsome Allen and whatevers look as dull as the incorrect shoes look comical