3 Men's Dress Shoes Must Haves

3 Men’s Dress Shoes Must Haves

Most men I have met spent a lot of money on dress shoes, yet they often buy the wrong kind of shoes, they don’t invest in quality or all of the above.  Whether you are just buying your first pair of shoes or if you already have many dress shoes in your closet, today’s video about 3 Men’s Dress Shoes Must Haves is for you because we all go on vacation and have to limit our dress shoe selection to the most essential and versatile models.o

Of course, we all have different needs and a white collar worker needs different shoes than an artist does, but these 3 models are something that every well dressed man should call his own.

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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.

Pediwear Collection Black Cap Toe Oxford - True Budget Oxford at 109.50 GBP.

Pediwear Collection Black Cap Toe Oxford – True Budget Oxford at 109.50 GBP.

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.

Cognac Brown Derby Full Brogue with 2 inch cuff

Cognac Brown Derby Full Brogue with 2 inch cuff


Shoe #2 – The Brown Derby

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.

Oxblood Cordovan Tassel Loafers by Meermin, with red blue striped socks by Fort Belvedere & red Indochino slacks

Oxblood Cordovan Tassel Loafers by Meermin, with red blue striped socks by Fort Belvedere & red Indochino slacks

Shoe #3 – The Oxblood Cordovan Loafer

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!

3 Men's Dress Shoes Must Haves
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3 Men's Dress Shoes Must Haves
Learn all about the 3 Men's Dress Shoe Must Haves & Why You Need Them In Your Shoe Closet and how to invest wisely so you get the most for your money.
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15 replies
  1. Attila Teleky says:

    Thank you for the information, ideas, and encouragement. I’m going to get a pair of brown derby’s and make use of my oxblood cordovan loafers and black cap toe oxfords because of your video. I also enjoyed your segment of polo shirts, and others.

  2. Deverout Graham cc says:

    What you write about style is that it is not about money but as you grow in style and confidence you should learn to buy and wear quality things, And learn how to wear and dress like a men ,And learn to invest in lasting quality garment.

  3. Ross says:

    I have not been reading this website for a long time, but those articles that I have read have been very interesting and of a high standard.

    The message within the article is interesting and useful but the writing is of a lower standard than I have come to expect on this site. The writing doesn’t flow, it is poorly structured and there are a number of spelling mistakes which makes it harder to read.

    Apologies for being critical but the standard on the site is usually very high.

  4. Frank Gadson says:

    Always wonderful helpful information I find your suggestions beneficial and put them to use all the time keep up the great work


  5. Yury says:

    Thank you very much for your infromation – really useful.
    If you could allow me to ask you for an advice with regards to the second pair of shoes I should buy.
    Having a white collar job (5 days a week in the office) and having few opportunities to wear casual outfit, I am having concerns about what to buy as the second pair of shoes. I bought recently black calf captoe oxfords which are really great, and know I am starting to think whether I should buy another pair of black shoes (e.g. semi- or quarterbrogued oxfords or derbies) or dark brown ones (again semi- or quarterbrogued), so that I would be able to wear them at work (with grey, navy or brown suits), but at the same time have an option to wear them in more casual situations (sporting them with different color shoelaces).
    Having that in mind I have to consider that in the Czech Republic where I currently live there are no many quality shoes shops, there is Barker and Loake though. Should I opt for black, brandy or burgundy.
    What would you suggest?
    Thank you in advance.

  6. Andrew says:

    Would the AE McAllister be an acceptable alternative to the brown derby? The closed-lacing looks more formal, but I can’t find something quite like yours in my very narrow width (A).

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