What is the most versatile brown casual gentleman's shoe? Pick one:. >(Brogued) Oxford shoe. >Derby shoe

What is the most versatile brown casual gentleman’s shoe?
Pick one:
>(Brogued) Oxford shoe
>Derby shoe
>Monk strap
>Dress boot
>Chelsea boot
>Work boot
>Moc Toe
>Penny Loafer
>Boat shoe

106 thoughts on “What is the most versatile brown casual gentleman's shoe? Pick one:. >(Brogued) Oxford shoe. >Derby shoe

    • Anonymous says:

      Meme shoe for soft boys who try to dress like tin tin characters and say they “garden” but really just have 2 houseplants

  1. Anonymous says:

    This may be controversial, but a 6" brogued wingtip seems versatile enough for literally anything imho. Can be dressed up for business or dressed down. A light color like cinnamon will pair with virtually any fit except maybe funeral attire.
    Derbies and Oxfords are classic business wear, but you can’t really dress them down at all.

    • Anonymous says:

      I personally find brogueing one of the most vile things in footwear, maybe because it triggers trypophobia or something, but I’d be interested to see an example of what you mean.

      • Anonymous says:

        I mean you could literally just google "6" brogued wingtip boot" or even a brogued wingtip oxford.
        terminally online much?

        • Anonymous says:

          I lack the imagination required to envision those in a casual/formal outfit. Post fit.
          >terminally online much
          You are here browsing an obscure Bangladeshi kite testing forum.

  2. Anonymous says:

    All of the above besides oxfords, brogues since they have that Oxford lace, derbies and loafers. Loafers could go with some linens but wearing them on jeans is jeetunclecore. If you want them with ornaments and shit go for both capped or wingtip shoes with normal lacing even better if they’re ankle length. Personally wearing brown leather toecap boots that can pass off for formal too in some cases

  3. Anonymous says:

    Regular old derbies are the most versatile, obviously, since they’re acceptable with suits and you see people wearing them casually at any sort of event where people are trying not to look like slobs. For a lot of men, a pair of mid to dark brown derbies are probably the only pair of shoes that they NEED to own.

    • Anonymous says:

      This is the truth. I have a pair of brown derbies that are my daily drivers at work now whether I’m wearing jeans or chinos.

  4. Anonymous says:


    This wtf, imagine wearing long lasting, natural material, european in origin, repairable footwear, CRINGE!!!! Wear the plastic and foam goyslop you hecking chuds

  5. Anonymous says:

    >most versatile

    >casual Friday
    Loafer, Chukka, Chelsea

    Monk Strap, Brogue

    >Why are you overdressed, Anon? Do you do ballroom dancing in those?

    >I am insane
    Dress Boot

  6. Anonymous says:

    I can’t decide between nice oxfords or monks. Maybe that’s my imagination but I think monks are most likely to get damaged because that thin leather strap is going to wear down quickly. I like the look though.

    • Anonymous says:

      realistically how often are you going to wear the monk shoes? if you get properly made shoes with real leather i think you’ll be fine.

      • Anonymous says:

        I’d like to make them my main shoes, so 1/2 to 3/4 of the year, with loafers for warm weather/lazy days and probably cheap chelsea for winter.

  7. Anonymous says:

    Got pic related but in black

    Have gotten nothing but compliments, and works well for both casual and formal events
    The only downside is the high price and having to wear tabi socks

    • Anonymous says:

      Based. I have a pair of suede brown Chelseas I’ve been wearing everywhere the past couple of weeks.

      how do you cope with them getting ruined every time a rain drop falls?

      • Anonymous says:

        I am at peace with the concept of things getting worn with use, so I see it as a regular part of their life cycle
        in the off chance I found something I want but couldn’t bear seeing wear out I’d only wear it in special occasions, case in point my tuxedo, but most likely I wouldn’t buy it at all

    • Anonymous says:

      They cost $400

      Oh boy. Look, it’s your purchase and if you’re happy with it, don’t look for validation online. But if you want my honest opinion: I think it’s stupid to pay that much for a sneaker. Sneakers are sportswear. This looks like a sneaker trying to be more of a classy men’s shoe, but it doesn’t work. I’d stick with the basics.

      • Anonymous says:

        They make a similar one in pebble grain, but I don’t like the look. It reminds me of car seats, or fake leather. Maybe that’s just me. Will I look weird for getting a dress boot for preppy/trad casual fall/spring outfits?
        I would rather kms

  8. Anonymous says:

    I have never seen someone wearing derbies that doesn’t look like a weird fruit and/or someone who’s trying too hard because he heard they’re fashionable

    • Anonymous says:

      Is this some new revelation for you? Of course, things that aren’t popular will attract weirdos, but they also attract people with actual taste and style who are able and confident enough to go against the flow. This is true with many things in life. Loser neonazis hate hebrews because they’re gross and unsociable, but the greatest chess player who ever lived was famously antisemitic as well. The derby is a classic shoe that can be pulled off in a multitude of ways if you take inspiration from the greats and don’t try to innovate on centuries old tried-and-true fashion.

  9. Anonymous says:

    Derby, light brown. consider a brogue cap toe or at least a cap toe.

    Been reading some about leather shoes. Here’s of the top of my head, feel free to correct.

    in general, by style:
    formal : oxford > monk strap > derby > chukka > loafer > boots : casual

    take that with a grain of salt, consider the following

    brogue makes thee shoes more casual. so do norwegian apron and split toes. cap toes too, but the least.

    shiny, lustrous leather is most formal (cordovan). grained leather is more casual.
    black leather is formal, browns and lighter browns are more casual.
    suede/rough up even more casual.

    soles: commando is most casual, rubbers (dainite/vibram) is casual, leather is formal.

    it’s not until you have to combine the shoes style/color with your pants that you go down the rabbit hole

      • Anonymous says:

        Ah I see. Originally thought because of the natural shine it can get (and price point), it’d be perfect as formal footwear. Some say you can still make it work for formal outfits but it seems to be discouraged in favor of calf, mainly because this last is thinner, more supple, and seems to produce a more "formal" crease. Cordovan is much more rugged and thick (I’ve never seen it in person) so it makes sense they’d make more informal pieces, I’d say great for boots you’re gonna beat the shit out of, perfect to go hunting at your castle’s backyard.

        • Anonymous says:

          shell isn’t thick, and can absolutely be dressed up and be worn formal. It’s just behind calf, you just don’t see it as much because its both expensive and rather rare outside of small footwear enthusiast circles.

  10. Anonymous says:

    I’m a big fan of my wholecut browns, but versatile they are not. For versatility it’s Derbys all the way, as other people in this thread have said. If the average Western man wore medium brown Derbys instead of sneakers half the time, he wouldn’t look like such a slob.

  11. Anonymous says:

    Personally I wear Longwing Brogues or Derby Brogues (I make the differentiation because the "brogue" in the image you posted is an oxford-brogue as it has the close laces at the bottom) or chelsea boots in all "gentlemently" occasions except a black tie events, for which I have a patent leather pair of oxfords.
    I have loafers for going abroad but they aren’t brown.

    The rest do nothing for me.

  12. Anonymous says:

    Classic, can’t go wrong
    like an oxford but uglier
    >monk strap
    strictly for instagram Italians and blacks going to prom
    >dress boot
    >chelsea boot
    >work boot
    great casual option
    >moc toe
    really really ugly
    unholy compromise between dress shoes and boots, avoid
    >penny loafer
    pure class
    >boat shoe
    ugly and tryhard

  13. Anonymous says:

    Idc about your question but I just want to say I think monk straps look cool and it’s just the current reddit advice to avoid them, like when they kept telling people to not get leather jackets because they’re dorks and thought everyone else is a dork like them.

  14. Anonymous says:

    I had no idea about the levels of formality between shoes so i bought dark brown oxfords but now i realize no one uses that type of shoes where i live, they all use derbies. Hope no one notices my flaps are on the inside.

    • Anonymous says:

      After the coof, dress codes have been steadily declining in my office. I just wear split toes or derbies, mostly in suede, nowadays, no use for my oxfords anymore.

  15. sage says:

    any recommendations for chukkas <$200. I just want one for casual use. cheaper but still good enough is fine w/ me ( got arizona chukkas years ago for like $40 just to try and it actually lasted for like 5+ years )
    are there any relatively cheap chukka that can last a while/not fall apart?

  16. Anonymous says:

    Loafers are the epitome of sexcore

    You will NOT be able to pull off unless you have a 10/10 face, 10/10 body and 10/10 charisma

    • Anonymous says:

      100% depends on the loafer… a chunky one like a doc or solovair looks good on almost anyone as long as you’re not fat and under 5’10

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