3 Dress Shoes Every Man Must Have

Welcome back to the Gentleman’s Gazette! In
this video, I’m going to highlight the three men’s dress shoes every man must have, what
you should avoid when buying dress shoes and I’ll even have bonus two pairs for you. In 1960, the Esquire author, George Fraser
once said “If you want to know a guy is well dressed, look down.” And boy was he right.
Shoes can really make or break an outfit, if you have a nice pair of shoes, it really
upgrades anything you wear. It can be a cheap suit, even if the fit is not ideal, a really
good, well – polished and nice looking quality pair of shoes will just upgrade your outfit
and make you look more professional and respected. On the flip side, if you have a cheap pair
of shoes, even the best fitting, most expensive suit will simply not look good because of
the choice of shoes so it’s extremely important to invest in a quality pair of shoes so you
get an overall great look. A good pair of shoes will not be inexpensive,
it will cost some money, but the good thing is you can wear it for a long time and so
the effective cost per wear goes down. For example, I bought my first pair of quality
men’s dress shoes in 2002. It was a wingtip derby and I’ve resold it many times and served
me really well. By now, the cost per wear is probably about 20 – 25 cents which us extremely
low compared to a pair of shoes that you buy for 50 bucks, but you’ll have to throw after
6 or 12 months because they’re already worn out. The cost per wear is much higher so it
really pays to invest in quality and to build a shoe wardrobe that you can wear with many
different kinds of outfits and that’s what we’re doing in this video today. Your shoe wardrobe should probably look different
than mine because it depends on many aspects. It’s about your profession, your age, your
style and also your environment and many other factors. However, these three men’s dress
shoes that I’m going to talk about today are really the best start for 99% of the men out
there and I’m sure they will work for you as well. These shoes are elegant, versatile
and will help you to round out your look and be more respected and well dressed. Shoe number 1: Black Cap Toe Oxford – I recommend
black cap toe oxfords to every man because it’s the first shoe you should start with.
It’s great for business suits, great for formal outfits. You can wear it even with a tuxedo
if you can’t afford a patent leather shoe which is fine and this is the first shoe that
you have when you’re a grown up. Even though it’s great for business suits and everything
professional, it’s not a great shoe for jeans or khakis so you should wear it more with
formal outfits, with suits, sometimes with combinations but not for casual outfits. it
should be made of box calf leather and it should not have any broguing. If you want
to learn more about Oxfords, what constitutes an Oxford and how it’s different from a Derby
or other men’s dress shoes, I recommend you take a look at our in-depth Oxford shoe guide
where we show you anything from how to actually lace an Oxford, how to buy them and how to
pick the right model for your wardrobe and budget. One thing to really keep in mind,
the Oxford is a dressy shoe, it’s a men’s dress shoe after all and so you want it to
be polished and you want ot be made of box calf leather and must have a leather sole
because it’s just more elegant that way. The second essential men’s dress shoe you
must have is the brown Derby in a full brogue or a semi brogue version. So what does that
mean? A derby has an open lacing system versus a closed lacing system. You can learn about
the differences here. A derby is a perfect shoe for all kinds of casual events, semi-formal
events. You can wear it with jeans and chinos even like suits. Although for very formal
outfits, you should probably go with the Oxford. It’s a great travel shoe and because it’s
more open, it gives you the option to fit even bigger feet. So most men would say the
Derby is a little more comfortable. With broguing, I mean that little hole perforation and simply
add some more casual character and you can have a wingtip or you can have a half brogue
which means just broguing on the cap, but it’s a straight cap. Both of these shoes are
extremely versatile and they should be a part of every man’s wardrobe. In terms of color,
brown comes in hundreds of different shades so for your first pair, try to go like a medium
brown because it’s super versatile, not too dark, not too light and you can just combine
them really well. Number three on the top three men’s dress
shoes is the Oxblood or the cordovan loafer. Now many men would have never thought about
an Oxblood or Cordovan loafer. What I mean by that, it’s a dark, red loafer and the advantage
of this color is that it literally works with everything. You can wear it with charcoal,
navy, khaki, off-white, green, brown, you name it. It works with every color and that’s
why it’s essential to have this kind of dark red oxblood colored shoe in your first three
shoe collection because it allows you to just add very few items and create a lot of different
looks. The color also works really well with any kind of suit, chino, jeans, combinations,
slacks, seersucker, madras and so there’s just endless variety. I suggest you get a
loafer because a loafer is slightly more casual shoe and you already have an Oxford and a
Derby. The loafer is even less formal but it allows you to really kind of wear it in
your spare time, on the weekends, afternoons, even at the office it’s perfectly fine. Specifically,
I would recommend you get either a penny loafer. If you want to know what the difference is
between those two, please read my article, my in-depth loafer guide where I talk about
all of these things. If you think it’s a shoe that just your dad
would wear, trust me there are lots of cool looking styles on different lasts. They are
really young and fresh-looking and modern and classy at the same time.Also, make sure
that you get a matching belt, matching in a sense of color because you always want to
pair the belt and the shoe in the same color otherwise, it looks off and it’s a faux pas
and people will think you don’t know how to dress. If you enjoyed this video, please sign
up to our email list and I will send you more of these videos right to your inbox and check
out our website, www.gentlemansgazette.com where we have a lot of material all about
classic men”s clothing and style. Thank you!


  • Excellent video as always! perhaps a video on shoe care? i always see people with shoes that are in amazing condition after several years of use whereas i have pairs where the leather creasing is widely visible and ruined. Thanks and keep up the awesome work!

  • Once again another great video and your outfit looks dashing! I would love to see a video on white tie one day, there isn't a single video about white tie and it's rules on this website.

  • =)

  • First class Sven, as always! Keep it up for your loyal listeners.

  • I thought one could get away with wearing tassel loafers with a less formal suit.

  • Could you do a video on cardigans and sweaters as well please

  • I own many black shoes, a month ago i bought a pair of brown shoes! Can u tell me when to wear them? And which suit color looks best with them? Thnx for the video!

  • What are your thoughts on suede oxfords?

  • Some brown are the most important!

  • Thank you for this wonderful and useful video again my good sir, might I ask if you are able to do a video on white-tie? And it's required etiquette, dress-code and how one may be invited to such an event. Anyways this video has been most helpful for me as I have now a good understanding on what dress shoes to invest in. Thank you again sir, cheers.

  • Hello Sven. There are tons of channels with similar videos but none quite as good as yours, I really like your work. One can see that there is a carefully thought structure in your videos, that makes info easier to process. You talk in a friendly tone at a comfortable pace and your examples are relevant to what is being said. Congratulations on a job well done!

  • I would rather die than be caught wearing a loafer. The style simply does not work in 2015. At least not if you live in Sweden and don't want to seem like a douche.

    Also, my personal opinion is that brogues look dressier than ones without.

  • I actually refuse to buy black shoes, leather just was never intended to be treated that way. Same goes for any color that is more paint than dye. If I cannot see the natural beauty of the leather, then the cobbler or designer did the worst of "sins". As such I boycott most black in my wardrobe, unless it can be paired with cordavon or brown…. Just my own personal style, by and by there is almost no good reason to spend the same on black as they can and do use leather that would be considered too blemished for brown or colors in which the grain shows through. Besides the dying process for black is extremely hazardous to the environment.

  • Can you talk more about ways of protecting your dress shoes during winter months. I think you mentioned galoshes, what else is out there worth investing on. I live in Canada and finding it hard to justify wearing my expensive shoes in the snow/slush.

    Thanks … love this channel, btw. Lots of great info!

  • ok what if your face is ugly

  • For casual or even being slightly formal, I always enjoyed formal leather sandals. They are comfortable and go very well with the traditional mens wear of my country, Bangladesh – not to mention the warm weather.

  • could u speak abit louder plz!!

  • should it be pronounced as Derby like you do or Daarby like Britishers do?

  • As a (relatively) young man interested in exceptional fashion, thank you very much for this video! I always looked up "wooden soled dress shoes" because I absolutely loved the sound but didn't know what the material was. No wonder I couldn't find it! Nothing says "a dapper man is coming" like hearing that sharp and weighty "tack tack tack" of (what I now know to be) leather soles. Much appreciated!

  • Which shoes (European brand) would you recommend to get in a price range of 180 – 300€?
    Italian, English, German?

  • I wear dress shoes since I was nine years old GREAT VIDEO…………..

  • I work in men's high end retail clothing where we make sale and make custom suit. I am always perplexed how many men miss this important part of their wardrobe. It can be somewhat disappointing when you work hard to get a gentleman looking their best by getting them in a great looking and fitting suit, only to look at their footwear and they have a pair of cheaply made shoes.

    I try to inform them of how the suit and shoes work in concert to complement each other. I tell them you just spent 2500 to 5000 on a suit but only want to spend 100.00 on a pair of shoes cheap Johnston & Murphy, Bostonian or other low end shoes seems counterintuitive.

    Men please if you can afford it, invest in a high quality dress shoe. Companies like Adlen, Allen Edmond, Peal & Co, Crockett & Jones, and Edward Green are great options and all have recrafting program. This will extend the life of your shoes for many years. I meet a attorney awhile back that had a pair of Crockett & Jones cordovan shell leather shoes for 20 years! Taking about cost per wear..lol!

  • I love your suit-shirt-tie-combination in this video!
    May I ask where you got your shirt from or how one can search for a similar one (it has wider stripes than the usual shirts)

  • Excellent sublime video, as usual.
    May I ask :which color of Polish wax or leather cream would you suggest for Burgundy shoes :neutral or the Burgundy one.
    Thanks in advance!

  • Hi Ralph, could you share the brand of that brown derby at 4min12sec. Looks stunning, I want ones!
    Great channel btw, keep up the great work!

  • Hi Ralph, i have been watching your videos about shoes. I understand from your videos that shoes are very important in our arsenal as gentlemen. Could you show us in a video how to cake care of our shoes, since I am sure lots of us have invested a lot on shoes. Thank you

  • sir is it correct to wear tassel loafers with a double breasted jacket?

  • great movie. thanks.

  • What is your accent?

  • So I just got a job in a business office setting that has a casual dress code, but sometimes requires more semi-formal outfits. My boss told me I could wear jeans if I wanted. I will mostly be wearing chinos and dress trousers, sometimes denim. So my question is, would it be better to start with a more casual shoe in this case that I will be able to wear more often? I do not yet own a suit and so would not have something to wear the more formal oxfords with. I was thinking for my first shoe to get an oxblood monkstrap or a brown blucher. I like the colour of the oxblood and really love the look of a monkstrap shoe. Is it unwise to get a monkstrap for my first dress shoe?

  • I want to see you in regular casual clothes.

  • Sven, what about sneakers and casual walking shoes with rubber soles. Is a gentleman not suppose to wear them?

  • question about the loafer in oxblood. would it be ok to swap out a loafer for a monk strap instead? I like the look of the monk strap more then the loafer and was curious what you think. I've seen guys pair monk straps with suits and jeans, so I was wondering what you thought. also single vs double monk strap opinion?

  • Just a quick comment: Derby is pronounced "Darby" in the UK at least where Derby is a city here but most of the people in the world say Derby

  • You know, I didn't think I would enjoy this video, but actually, it's cool.

  • Should you frequently clean the soles of your shoes when they are made of leather? I can imagine that they might last longer that way.

  • How would you rank a monk strap, derby and an oxford in formality from highest to lowest? 🙂

  • I live in Scandinavia where the weather is volatile most months of the year, that is wet. Would you still recommend a leather sole on an Oxford dress shoe or would you recommend a rubber sole? I have some pairs with leather sole, but I'm always conscious about wearing them when it could potentially be raining. I know that a galoche (rubber cover) is a good option, but when going out partying or going on certain events this is not fitting because I do not know where to store them etc. What would you recommend?

  • I just noticed you have quite a bit resemblance to ralph machio of karate kid!

  • What do you think about Redwing heritage collection.

  • Can you wear the ox blood loafer with a suit?

  • Advice question, I am Catholic religious brother who will be working as a teacher. I wear blacks for work(collar and pants) but prefer to wear tan khakis when out and about with friends. I want to get a derby that can work for both the classroom and going out. What is a good shade to go with? Would Oxblood work or am I just in a jame due to the large amount of black in my work attire?

  • I was planning on going for a classic black captoe Oxford, a brown full brogue Oxford, and an oxblood wholecut Oxford. Thoughts?

    I feel it potentially lacks versatility due to 100% Oxford, so may change the brogue to a Derby.

    Any advice from yourself or your viewers would be much appreciated.

  • thank you for the inspiration and education

  • Another great video.

  • i'm 15 and i enjoy this is that ok

  • it is perfectly fine to wear a belt that is a different color than your shoes. and it is certainly no faux pas

  • I am not trying to be edgy but 1:53 isnt true, if you calculate 50/(6*30) u will get about 28 cents per wear. So the cost is about the same and not drastically higher as you said in the video.

  • At least I got this one right…

  • Does anyone know a version of the gentlemen's gazette for women? My wife would love to know?

  • Hello sir!
    Can you present some alligator / snake skin shoes?
    Thank you in advance!

  • FUCK im in college, I'm gonna go even more broke starting my shoe collection

  • Hi I have wide feet and my shoes break all the time I want to invest in a good pair of shoes but afraid they will get damage can you please help me.

  • Should I get suede or full grain leather loafers? This is going to be my first pair of loafers. And I wear navy Chino with a grey shirt for the rest outfit. Thank you sir!

  • So uhh.. If i wear a brown shoe i should wear a brown belt too?

  • I tend to take my Santoni shoes to my cobbler and have him line it to protect the sole, he uses a rubber liner and brass to hold the toe down do you think that this is correct to do rather than keeping a leather sole. what do you think sir.

  • Where is this guy from? He has the most amazing accent.

  • All I ever see is hate towards the rubber sole but never an explanation on why it's a bad thing. Why is it better to have a leather sole? From the example picture that he uses at 4:07 it looks like that rubber sole has better traction but apparently it's taboo to use.

  • Can I simply say what a relief to find

    someone who truly is aware of what theyre

    speaking about on the internet. You definitely know how

    one can convey a problem to gentle and make it important. More

    folks must read this and perceive this side of the story. I cant consider youre no more widespread because you definitely have the gift.

  • I recently discovered your channel and would love it if you would demystify cordovan/horse-leather shoes. Thank you, your channel is very informative.

  • Man, that is one fine looking jacket. 👍🏻

  • Great content. Enjoyed and informative. I just bought a full brogue black shoes, hopefully it matched my black trousers and belt

  • I can't tell if he's telling the truth… his voice is simply that distractedly soothing.

  • Good work

  • can you recommend a good pair to buy am looking for some oxfords but unsure what to buy thank you

  • muy buen video

  • I am really enjoying these videos. so much knowledge treasure over here 🙂 I am really happy! came with zero knowledge on shoe and learnt a lot….

  • when i was very little., my grandma told me shoes takes half of your outfit,. all the rest the another half

  • What is box calf leather? 🙂

  • What is the dark brown shoe brand and style at 4:16? Thanks!

  • why did this guy always put his camera 50cm away from his face, so uncomfortable to watch a man's big face on my little monitor.

  • I have a shoe repair shop and it is unbelievable how many people don’t care about shoes. I see wealthy people who have to dress up every single day to work and they wear 100 dollar shoes. I just don’t get it. Part of the issue is the lack of availability of good shoes in my area but that’s probably because of lack of demand. I’m sure if there was a market for higher end shoes someone would sell them. These people think they are saving money I guess. Really they are spending more and getting less.

  • Is ox blood the same color as burgundy? Is burgundy a great match for a navy suit?

  • "Look Down."
    -Shawshank Prison Guard's Handbook, 1967 Revised Edition.

  • For once, I actually like what you're wearing, good stuff… nice video too

  • That tie looks beautiful ❤

  • I am not a huge fan of a brogue pattern on shoes. It reminds me of a 70's Texas oil tycoon owner a bit much.

  • About to enter the professional finance world – with your channel I found gold!

  • I bought a pair of Manchester tassel loafers from Allen Edmonds from a thrift store. The shoes, when still made and sold, went for $400+. I got them for $9. They were badly scuffed, scraped, and scratched, but they were wearable and hade developed a desirable patina. I got out my disinfectant and my polishing materials. I used brown cream polish and used black cream polish at the toe and sides to supplement the patina and make the damage of age more subtle, and it was a complete success! $9, and some tlc, got me a pair of shoes that many would spend hundreds of dollars for, and they look fantastic!

  • excellent!

  • Thank you so much. I've followed your advice and now i got these 3. I got them all from Mario Minardi. Though they may not have a 600 bucks shoes, i'd say they're one of the best for men shoes in my country.

  • Hi Sven. Great channel. Do you recommend leather bottoms on derby shoes as well? It seems like you recommend rubber bottoms only on dress boots for rain. Is that right?

  • Do. Not. Wear. Belt. With. Suit.

  • I'm not a buisnes man or a doctor or any other important kind of professionals, I'm a regular guy with a non profession career, so I don't think that I can wear these things one day because there is no event or place can handle it for me , although I can offer it easily but I feel sorry for not wearing it .

  • this is the most dapper ive heard you annunciate the opening line

  • math check, wearing $92 shoes every day for a year is also 25c per wear

  • Monk strap!!!

  • I want a pair of whole cut, red dress shoes. Something from Stefano Borella. I am not sure how to style it, but I'm just going to wear the heck out of it.

  • Raphael é o teuto-brasileiro mais elegante do mundo. Vc é um homão da porra, rapaz! Um abraço.

  • Forgive me for being late to the party.

    Great suggestions, especially about buying quality shoes. One thing I would point out is, you can get good shoes on sale or go with factory seconds, for not much more than a cheap pair of shoes.

    As for the specific suggestions, they are solid, but let me offer a little bit of a perspective. I am in one of the few professions where I have to wear a suit almost every day and I haven't worn my cap toe oxfords with one of my suits in several years. So what do I wear with a suit? Black monk straps. Black plain toe Derbies or Bluchers. Whole cuts in dark chili or light brown. Dark brown or Walnut half brogue bluchers. Or even dark grey Chromexcel leather full brogues for a change of pace shoe or as a slightly dressier alternative to a loafer.

    On the other end of the scale is the whole loafer thing. Don't get me wrong. I bought my son pair of black loafers last year because he needed a black shoe for his high school orchestra concerts, and he just isn't ready for black oxfords yet. But I have found the loafer just isn't for me. i used to wear penny and tassel loafers, but I have found they don't stand up to our winters and in summer, I am fine with lighter colored lace ups.

    I am not saying my judgment is any better than anybody else's. But I would say it depends. It is possible that in Boston or in New York, for example, that Black cap toe oxfords isn't too dressy. But I find in the Midwestern city I live it, it is, for all but the most dressy occasions.

    Might I suggest that you suggest 5 possible shoes, and that the viewer pick 3 depending on personal preference and lifestyle. For example, Black oxford, a good wingtip, brown blucher or derby, loafer, and maybe a good pair of boots.

  • Well stated Sir!

Leave a Comment

Your email address will not be published. Required fields are marked *