The First 5 Dress Shoes Every Man Should Buy & In What Order | Upgrading Your Shoe Collection

The First 5 Dress Shoes Every Man Should Buy & In What Order | Upgrading Your Shoe Collection

Gentlemen, Antonio here. All right. Quick question for you. What are the most expensive shoes that you
own? Let me know down in the comments, I want to
hear from you guys. Now, believe it or not, I bet I can guess
the most expensive shoes in your closet. How can I know this? Because, guys, it’s easy. The most expensive shoes you own are the ones
that you never wear. Make sense? If you go out there and you buy $100 pair
of shoes and you wear it once. You go out there and you buy $350 pair of
shoes and you wear them 350 times, guess what? $100 per wear, a $1 per wear, which one was
the better deal? Gentlemen, shoes are one of those items that
you want to get right because good shoes are expensive, however if you get the right pair
in the right order, you’re going to get your money’s worth out of them especially if you
take care of them. In today’s video, I’ve got five pairs of shoes
I’m going to recommend you guys and the order to purchase them. We’re talking about dress shoes here. I support this with a great free e-book. Go check it out, guys. You can download it, it’s absolutely free,
85 pages of solid information, Man’s Ultimate Guide to Dress Shoes. Now, this is just going to be, you know, a
little quick part of it, but the article that supports it is in that free e-book. And, really quick I’ve got about twelve samples
here that I’m going to be running through to give you guys an idea of the five shoes
that you need to own and variations of each of them because when it comes down to it,
gentlemen, you need to make the right decisions for your lifestyle, your professional need,
your personal need, and your style wants. So, those are things I’ll going to go into
this. There isn’t an exact right five pairs of shoes. However, I want to get you thinking about
that. When you start to think about this and you
pay a little bit more attention, you’re going to make sure you make your own smart purchasing
decision. All right? Let’s get into the first pair of shoes that
you want to own. We’re talking about balmoral oxford, something
that has closed lacing. Now, this is a wholecut dress shoe, not technically
in there, but I put it here because guess what? It’s pretty much got the elegance simple look,
but here it’s going to be a more classic one with the closed lacing system. This one has cap toe, it’s in dark oxblood
color. This will work fine for wearing with a suit
and that’s what you want your first pair of shoes dress shoes to be able to is to wear
them with a suit for a wedding, for a funeral, anytime you’ve got to wear that. You’re meeting with the president, meeting
with the CEO of your company, you’re simply getting dressed up for your little girl’s
communion. This is when you want to look your best and
you need to have that pair of shoes that works with it. Now, black is going to be the de facto color
for a lot of you guys. Be careful though even though you’ve got closed
lacing on this pair of shoes, we start to see a little bit of broguing here. So, once you start getting into cap toes broguing,
all of a sudden the formality of it is going to start to go down, you could still pull
this off with a suit though. Guys, by the way, this is Paul Evans. Most of the samples here I’m going to show
you were Paul Evans. This one right here is made by Church’s, I’ve
got some Cheaneys, I’ve got Alden. There are great companies out there. I go into a lot more detail in that e-book,
but the first pair of shoes that you want to start with balmoral oxfords. Next, let’s go on to Bluchers. So, the second one and the big difference
here is going to have an open lacing system, not a closed lacing system, so that’s the
key differentiator. You’ll find that these shoes in general are
going to have may be broguing or they’re going to have ornamental stitching, they’re going
to be lighter in color oftentimes. So, these are going to be your more casual
dress shoes. These you can still sometimes pull off with
a suit, but they’re going to look better with occasionally dark-colored jeans at the probably
the most casual. And then, but you can always dress them up
with a pair of, you know, gray flannel trousers, just regular dress slacks maybe with a sports
jacket. These are going to be very versatile. These are great and I think should be the
second pair of shoes in a man’s wardrobe. Next, let’s go to the slip-ons. So, I’m going to have a wide variety of slip-ons
I’m going to show you. The reason I love slip-ons is that they’re
casual, they’re comfortable. Guys, when you are traveling you’re going
to the airport very easy to take on and off to be able to go through that metal detector. They come with a wide range and most men don’t
think, I mean the monk strap. Not technically a loafer, but I’m going to
lump into the slip-ons because you don’t have to lace anything up. And I love, I mean single, double, it doesn’t
matter where you go. Again, I like to go with in general darker
shoes and I know I’m not talking about color a whole lot there. Again, I go into color in the e-book, so you
can go check that out. Tassel loafer. Now, this is going to be a little bit less
formal than the monk strap, but I find many men especially in the United States will pull
this off with a sports jacket, odd trousers combination. You can wear it with jeans, it’s going to
look great. Occasionally if it’s in a very dark color,
maybe a black color, you can actually even pull it off with a suit although you want
to be careful in bigger cities. Now, all of a sudden we’re having more fun. So, this is a suede penny loaders. This suede right here is going to give it
a much more casual feel. We’ve got the old driving shoe, comes from
the moccasin. Notice this right here, it’s going to have
this is something that you can wear around in your car. When it has a bottom like this, you’re not
going to want to wear it, you know, walking around too much because it will wear quicker,
but if you want something that, you know, you spend a lot of time in your vehicle and
you’re or around your house and you want a nice slipper, this is going to work out great. The fourth shoe style that I’m going to talk
about, gentlemen is the dress boot. So, right here I’ve got a chukka. So, chukka comes out of the English, I believe
it’s the word time desert boot. It has since changed quite a bit. This one right here as you can see is in a
dark brown. Again, Paul Evans is the company that made
them, but checking this out right here. It does have an open lacing system, so that
right there is going to make it much more casual. I think this looks best with a pair of, you
know, gray flannels maybe trousers with an odd jacket with jeans that looks great. You’re also going to see Chelsea boots and
those look really good with everything I just mentioned. And because they’re going to be simpler in
design, they actually sometimes can be worn with a suit. Now, I know many of you guys are saying, Antonio,
I can’t believe you’re recommending wearing boots with a suit. However, if you live in New York City, you
live in Chicago, you live in an area in which you get some bad weather, you understand what
I’m talking about. Because you want to wear boots whenever the
weather is just not really cooperating with you, you’re getting rain, you’re getting some
sleet, you’re getting some snow, you still need to wear a dress shoe and you want something
that’s going to go up a little bit higher on the sides and protect your ankles and socks. All right, gents, so you’re wondering what
is the fifth dress shoe that I’m going to recommend. Guys, I want you to go back and look at the
four that I just mentioned, find out which one you’re wearing most often and repeat it
maybe in the slightly different style slightly different color. So, not to fully repeat myself, but, guys,
within each of these categories, I gave you about three examples not just in color, but
in small variations and size. So, as we’re going through I didn’t really
even talk about brogues, wingtips, but these would be a great addition as a fifth shoe. Gentlemen, when it comes down to it, you got
to find the right shoe for your need. In general though, I like to go simple, I
like to go in darker colors and I like to stay within one color for most of my shoes. For me, it’s going to be oxbloods and dark
browns. I find that those are going to match most
of everything I have in my wardrobe, I can dress them up, I can dress them down. I’m not necessarily a black shoe man, however
some of you guys are going to love the color black and if that’s your case, then make sure
that all of your shoes kind of work there and the reason is that is also and you’re
building up your interchangeable wardrobe. Gents, as mentioned all the support my free
e-book 85 pages of solid information. Go grab it here. That’s it. Let me know what you think in the comments
and I’ll see you guys in the next video. Take care.

100 Replies to “The First 5 Dress Shoes Every Man Should Buy & In What Order | Upgrading Your Shoe Collection”

  1. – Click Here to Read the Article The First 5 Shoes Every Man Must Buy

    Are you ready to up your style? Click here for the BEST style course on the planet! – Click Here To Download This Free 85-page eBook on Men's Dress Shoes

    Video Summary:

    1:49 – #1 Balmoral Oxfords
    3:06 – #2 Bluchers
    3:49 – #3 Slip-ons
    5:17 – #4 Dress boots
    6:33 – #5 Repeat – Click Here To Download ALL of my FREE Products – Click Here To Download Our FREE App for iPhone and Android – Like Us On Facebook! – Follow Us On Instagram – Tweet Us! – Follow Us On Pinterest

  2. My most expensive shoes are my super fucked up running shoes i've been using since forever for university, gym and pure running

  3. The most expensive shoes I own are actually boots. They are Iron Rangers from Red Wing. cost me about $300, and were totally worth it. I love them.

  4. You should make a video that covers, in a really quick fashion, every type of footwear every man should have. You know, your 5 dress shoes, how many boots and the types, what casual shoewear, etc. I'm interested in how many shoes you would recommend.

  5. Love the Corthay shoes, I buy them and I rather have them on display like some folks collects those Michael Jordan's shoes

  6. For the young ones out there, you should do a video on how Nike is selling Air Jordans at outlandish prices all while having them made in china at pennies to the dollar. Perhaps they should take a little less in profits and hire American workers to make the shoes that they sell in America. When a friend of mine that works in the in the industry told me that Nike pays an average of $16 for a pair of Jordans my jaw nearly dropped.

  7. The ideas you give are good. But your choices of shoes make me sick. Those 5 shoes displayed in there is the worst I have ever seen. Also I don’t know if you owned any Redtape before. Those were the worst quality branded shoes I have ever used. People can get far better shoes adding few bucks on the cost of it

  8. I have very extremely wide feet, so got fitted for a pair of bespoke E. Vogel's 2 strap Jodhpur. They can be dressed up or down. I'm not remotely a dandy in fact a do a lot digging at Goodwill, but when comes to shoes I'm all out. D2Shoe for cycling/racing, Hersey Running for informal and E. Vogel for formal. Pretty hard to go back to off the rack shoes once you go full custom, even with the waiting lists and cost.

  9. In Europe, (Italy, Austria, Germany, and Denmark) they wear lace up dress boots for winter. My brands generally are Ecco and Johnson & Murphy.

  10. Black oxfords with bulled toe caps, initially, but I looked far to formal for an interior designer. Now I probably spend more time in derby brogues, although I think I'll be getting a pair of chestnut brown double monks for use with a mixed grey/navy odd suit trouser/jacket combo.

    Having said that, a pair of oxford brogues would be nice.

  11. My most expensive shoes are my brown Camper Blucher/Derby (I forgot which it was) and black Ecco Loafer (for dress shoes). Both are around $100. I don't have any shoes touching the $200 range. All are below that haha.

  12. There are quality shows out there that will not break you. He really doesn't mention that his audience is really 6 figure plus income clothing and shoes. He never talks about affordable I am not sure what the target audience is but $350 shoes is so far out of my tax bracket.

    You can still kill it style wise and spend a quarter of what he does. You just have to know where to go and making less items work more ways. I appreciate his advice and insights though, maybe a lottery win will let me spend like that.

  13. Antonio… thanks for all you do. Great videos. Any discussion or opinions about formal and casual Cowboy boots . Is there a place for them. I live in Oklahoma and they are everywhere.

  14. 420$ Allen Edmonds Long Branch Wingtip Boots. I wear them pretty much everyday in the fall and winter. Super comfortable, well constructed and i love the way they're aging. My only reservation is the sole is soft and wearing out quicker than expected, correctable when it comes it to having them resoled

  15. Great Video! This is some valuable advice you're saying about the most value per wear. I made a video very similar to this with some other brands, (not sponsoring any of them though). Please check it out ya'll

  16. Could not agree more, man should never try and save money on shoes. My most expensive pairs are all around €400, Church’s, Tod’s and Diemme, but it’s doable to get quality shoes for €200, at least in sales, just not dark brown brogues or dress shoes at all, but for sneakers and casual shoes, Fiorentini+Baker, Hogan, Sanders for Chukkas, Andrea Zori and Premiata for sneakers, I even found great Officine Generale leather sandals for €130 a few weeks ago. One should care for shoes properly, though, never wear the same pair two days in a row, always keep them on shoetrees and apply the Sapphir regimen a few times a year

  17. Love this review! I’m rather new to this so this is very helpful. One question I have is I need a pair of shoes that would look good with a pair of jeans and maybe a polo or button down shirt. Would monk straps or wingtips work or is that too dressy? Also would brown or black be better for that style?

  18. Mezlan Platinum Custom 3935.
    I chose the Tabac colored Ostrich versions.
    I payed around $800 and rarely wear them.
    I'm saving up for a pair Belvedere "Ernesto"
    Emerald Green Crocodile/Velvet slip-ons.
    As you can guess, I like my dress shoes
    kinda loud and obnoxious. =P <3 your videos!

  19. 5 Dress Shoes Every Man Should Buy..
    Very good knowledge of shose i have hear.
    I have most of these shoes.
    Expect for the Dress Boot.
    I plan one a or two pares.
    Thank you.
    I continue to work on Architectural Houseing Development Project.
    This weekend plan to meet with a Personal Accounting.
    To share my Millions Dollars Housing Development Project.
    I will keep in touch with you.
    Thank you.

  20. So I started off with Bostonian basic oxfords and also had wingtips. Unfortunately the heel design changed and caused bone spurs and tendon damage. Changed to Johnson Murphy and was much happier after the spurs receded.
    I work in an office, sometimes meet clients, contractors and on occasion go to construction sites.
    I must get EEE widths and JM and a few other makers have stopped making EE and EEE widths. Short of getting a custom made shoe, where do I go?
    Also I went thru 2 pair shoes a year, leather soles just wore thru. I added rubber bottoms which helped to an extent. How much of the sole is typically replaced and how often can this be done?
    First concern is getting EEE shoes.

  21. Спасибо, ты лучший. Смотрю в русской озвучке. Но скоро выучу английский и буду смотреть только оригинал.
    Thank you, you are the best. I look in the Russian voice acting. But soon I will learn English and I will watch only the original.

  22. My most expensive shoes are casual sneakers from RedTape worth $40 but I got it on sale for $15
    PS:- I live in India

  23. Antonio, thanks for the good info. My collection: Ace Marks Italian double buckle burnished brown, Cole-Haan pointed toe in black, Florsheim Brogue wingtip in black and brown, Cole-Haan black round toe, thick sponge -type sole single comfortable and some others from Mexico that are very attractive and comfortable. I can see why Emelda Marcos had such a collection of shoes.

  24. For me it’s a pair of Allen Edmond walnut Chelsea’s I got for 360 (originally they’re 500). Love the quality and design so I definitely subscribe to the idea that you get what you pay for

  25. My expensive shoes are these quaility-built dress shoes that have lasted 15 years. But they're square-toe'd! Out of style apparently. Waste of investment.

  26. I have a pair of ostrich loafers from bally that was handed down to me by my father.He wore them for 20 years,have been resoled and repaired a few times. Shoes are really an investment. Buy good shoes it will probably last a lifetime.

  27. My most expensive shoes are my bespoke pair of button boots in black calf leather and a beige suede insert.

  28. My most expensive shoes are John Lofgren Engineering Boots. And I wear them everywhere but work. A little over $900.

  29. Quick summary:
    1) Balmoral Oxfords
    2) Bluchers
    3) Slip-Ons
    4) Dress Boots
    5) Another pair of whichever shoes you wear the most.

    You're welcome.

  30. I own a pair of used black shoes that I just bought for $20 and they are super-stylish, a completely deluxe version with an amazing elegance. The Coolest shoes I have ever come across. Period!

  31. 200$ OG ultraboosts the literal comfiest and one of the most versatile sneakers with such a clean and unique silhouette

  32. My most expensive are a pair of Alden full brogue cordovan wingtips. I wear them 3 days a week, so I guess I'm doing things right.

  33. Hmm. OK, you make some good points and you hit some major categories. But I have a few bones to pick here.

    I think the old rules about black balmoral oxford being the correct shoe to wear with a suit are a bit outmoded. IMO, you can wear any of the styles you mention with a suit (and can even get away with doing so wearing a dress shoe with a Dainite or Vibram mini lug sole).

    If you find a dress shoe you love with closed lacing, or a Blucher, or a Derby, or even a Monkstrap, any of those will work in all but the the dressiest occasions in black, dark brown, oxblood or dark chili. Indeed, I would argue that perhaps in today's world where many men don't ever wear black tie or a business suit, the first pair of dress shoes should be dark brown, oxblood or chili, and be somewhat less formal, perhaps full or half brogues. Or just maybe a plain Derby in a rich, dark brown or dark chili.

    You don't mention anything about summer vs. winter style, but if you get into a 4th, or 5th shoe, perhaps a lighter color such as walnut, or light brown might work for warmer weather.

    I do not favor loafers, and frankly, though i see some middle aged men wear them, a lot of guys I see wearing them come across as arrogant D bags. Don't know why, and maybe just my problem. On the other hand, I do think the loafer might be the perfect first dress shoe for a younger man, who will probably use them in more casual modes of dress, and occassionally for a formal occasion, or job interview.

    I find myself scratching my head about the whole dress boot thing. I only know a handful of guys who wear dress boots. I would humbly suggest that the aspiring snappy dresser holds off on the dress boot until he has a bigger collection of dress shoes.

  34. The most expensive shoes I own is a pair of black “Higgins” Chelsea boots that are Goodyear welted in Spain by Mezlan. They cost 450 USD on their retail website.

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