The First 5 Dress Shoes You Need To Start A Shoe Collection

The First 5 Dress Shoes You Need to Start a Shoe Collection

When you start a wardrobe, versatility is key because every item has to work with one another. That way, you get the most combinations possible with the fewest items in your wardrobe which save you money. Of course, the same is true for shoes.

All the shoes in this video and article were provided by Ace Marks. who collaborated with us on this one. For a special deal, please use the code gentleman for any purchase on their website.

Over the years, I have acquired quite a collection of shoes and today, I have probably several dozens in my collection, however, when I started at zero, things were quite a bit different.

Don’t Get Lured In By Sales – Buy The Shoe Style That Is Right For You

I remember being lured into buying a pair of the Lottusse Goodyear welted dress shoes, they were black, and I thought it was a staple, and after all, they were Goodyear welted when they were on sale.

The problem was their sole was extremely stiff, so it was very uncomfortable to walk in them and they were also a little on the big side but I thought I was getting a deal and so I bought them more importantly, stylistically, they were kind of odd because they were a derby shoe which is more casual than an oxford and they were wingtips with full broguing. At the same time, they were black so it was really hard to combine them and I ended up not wearing them, so it was an inferior investment.

By the way, all of these shoes are from Ace Marks, a supplier of handcrafted Italian men’s dress shoes and I liked them because they are hand burnished and they provide an excellent value under $300. I’ve had their shoes in my closet from the beginning, and I liked them quite a bit because they fit me exceptionally well. Are those the best shoes money can buy? Heck no, but they provide a remarkable value that you won’t find otherwise in this price category.

5 Dress Shoes You Need To Start Your Collection

1. Black Oxford Shoes

It’s an all-time classic, especially as a captoe. You can wear it for business, you can wear it to the funeral, and you can wear it for any formal event out there. Also, unlike brown, black comes just in one shade, and so you don’t have to invest in dozens of black shoes, but one is a staple that you must have.

How Do You Wear A Black Oxford?

You can wear it with two-piece suits, three-piece suits, particularly in navy, charcoal, and grey, and any other business appropriate suit. It’s also good with blazers, maybe a navy blazer with gray flannel slacks or you can wear it with your tuxedo for Black Tie events, your dinner jacket, alternatively, also for a white tie or formal morning dress. Probably the most famous black oxford is the Captoe Balmoral style without any form of broguing, however, if I could just invest in one pair, I’d go with the black oxford whole cut because it’s impeccable all around, there are no seams, no extra cap toes, no broguing, and because of that, you can wear it even with the most formal ensembles such as white tie.

The Wholecut Is The Most Versatile Black Oxford

A whole cut is called that way because it’s made from one piece of leather. If you go with bespoke models, sometimes you’ll find a piece that has zero seams off the rack models always have one seam and it’s in the back so it’s very subtle and it’s a very clean silhouette that works for classic, stylish people, as well as minimalists alike. With a black whole cut Oxford, make sure you avoid the medallion on the tip of the shoe that way, you can honestly wear it for all occasions that are formal. This Ace Marks model whole cut has five eyelets which are very classic and an elegant long last with a timeless round toe.

2. Brown Derby Full Brogue Wingtip

A derby is less formal than an oxford. The derby has an open lacing system, and because of that, it’s more flexible, so when your feet are tired, and they swell and get bigger, it’s a more comfortable shoe than an oxford. Because of that, I like it for traveling. I would choose a medium brown color such as this antique brown cognac from Acemark; it’s very versatile, and because they are hand polished and hand burnished, you see different shades of brown at the tip of the shoe than for example at the bottom. The holes you can see in the shoe is called broguing, and it just gives a shoe a much more casual character.

How Do You Wear The Brown Wingtip Derby Shoe?

Basically, you can combine it with anything you know with suits, sport coats, corduroys, slacks, chinos, denim, you name it.

medium brown penny loafers

Medium brown penny loafers by Ace Marks

3. Casual Loafer

It’s a slip-on shoe, it’s relaxed, it’s an entirely different style from the other two, yet it’s a timeless classic. It’s straightforward to dress up or down, and they come in different variations; you can have tassel loafers and sometimes people think they’re old-fashioned yet you can actually have them quite young looking and modern but if you don’t like that, go with a penny loafer because they’re really classic and they’re called that way because you used to be able to put a little penny in the front opening.

For versatility, I’d go with a different shade in brown than you chose for your derby wingtip. Ideally, something maybe with a reddish undertone or something medium brown, in any case, it’s something different.

How Do You Wear The Casual Loafer?

It’s an excellent shoe for non-formal outfits; you can also wear with seersucker, or in summer maybe without socks and you should only avoid them with double-breasted suits.

I chose this model from Ace Marks in medium brown because it has a lovely patina on the front, it has also a very nice last that hugs my foot in the middle and that way my heel doesn’t slip out when I walk which is extremely important because you don’t have a lace-up system that keeps things in place.


4. Reddish Double Monk Strap

I’d invest in a double monk strap in a reddish color because it’s very versatile, it’s stylish, and it’s young, and it’s just different than all the other shoes that you already have in your wardrobe at this point. This model from Ace Marks comes in a brandy antique brown which means it was hand polished and hand burnished to achieve different color tones. It’s made on a very clean last, there’s no broguing, no cap toes, and the buckles are exactly in the right place and I find the shoe extremely attractive.

Unlike with black, with brown, you want different shades of the same color even though they’re very similar because sometimes one shade pairs a lot better with a suit with some pants than the other. Because you are just starting out, make sure the new brown tone of your shoe is different than the ones you already have in your shoe closet.

How Do You Wear Double Monks?

You can go just with jeans, or with slacks, maybe polo shirts, some people even just have a t-shirt, maybe sweaters, or cardigans, but it’s also very good with a suit; either a three-piece suit, two-piece suit or a sport coat combination. If possible, get a belt in the same color and also try to get a buckle that matches the color of the buckle on your double monks. In this case, if you buy this Ace Marks double monk straps shoe, you can also get the matching belt out of the same hand polished leather with a silver buckle, so it’s immaculate and dapper.

5. Medium Brown Half Brogue Oxford

Here I have an Ace Mark shoe in a lighter antique tan which is once again different than all the other brown tones in my wardrobe. It has a captoe with nice broguing, a medallion, and it’s less casual than the full wingtip derby shoe. I’m adding it to the collection because it’s an in-between the more formal oxford and the more casual derby.

It fits right in between because it doesn’t have a wingtip but it has broguing, yet at the same time, it’s an oxford and not a derby. I had a model like this, and I wore it extensively when I was a student because it would always go with everything I had at the time in my wardrobe.

How Do You Wear The Half Brogue Oxford?

It’s a super versatile shoe that you can wear with almost any suit. It is dark enough to be worn to the office, it’s brown enough to be worn with tweed, and everything in between. In my opinion, it’s a great spring summer and fall staple, and you can even wear it during milder winters.

Hand burnished captoe half brogue Oxford by Ace Marks

Hand burnished captoe half brogue Oxford by Ace Marks


So if you invest in these five shoe styles, you genuinely have an incredibly versatile dress shoe closet, and you can hold off on investments and maybe spend on other parts of your wardrobe. If you’re interested in a quality shoe with a flexible sole made out of a soft Italian leather, I urge you to take a look at Ace Marks because they have the classic styles in a very elegant last that is very attractive, timeless, and it won’t break the bank.

The First 5 Dress Shoes You Need To Start A Shoe Collection
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The First 5 Dress Shoes You Need To Start A Shoe Collection
The five must-have dress shoes to build a versatile shoe collection.
Gentleman's Gazette LLC
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16 replies
    • Dr. Christopher Lee says:

      I’m personally a fan of brown suede, double monks or laced. I just recently read that for carded wool suits/trousers (and generally, those with donegal/flannel/rough wintery textures) suede shoes should be worn as a rule.

      • Sven Raphael Schneider says:

        Suede is great indeed, unless you live in a climate where it rains a lot ;). I like the softer, matte look of them. I do not think you should wear suede exclusively with tweed and flannel, especially not when it is snowy outside, but it is a good option for dry fall weather. Maybe I’ll make a video about the first 10 shoes, and suede would definitely be part of it. Of course, you can also add it as your 2nd or third pair if you like it and it works for you. These are not cooking recipes, just general guidelines.

  1. Mosfek says:

    Great article as usual. I recently bought an Ace Mark Single Monk strap in Brandy color. Comparing to my 5 pairs of AE shoes, I really like the AM’s patina and their last which is a lot sleeker than AE classic 65 last. I found the AE is a bit more comfortable because of the in cork sole and their leather it bit thicker but nothing that would sway with my next AM purchase. Also, AE usually runs around $400 and AM around $300 so its a great shoe from the price point. I think its good have combination.
    For the Gentleman’s who have a high instep (me), so far I haven’t found loafer that fits me comfortably. Therefore I prefer monkstraps.

  2. Basil Damukaitis says:

    It is a nice idea to have loafers but it should come with a warning. For people with flat feet/fallen arches, or with any other irregularities, no loafer will ever fit correctly, or even look right,

  3. FMR says:

    I enjoy the site, and although this is a good article, I would suggest some changes.
    Most of my suits are grey or blue, as are most gentlemans’, and frankly black shoes work better than brown with these colors. If you only have one pair of black shoes you will wear them multiple days in a row, which creates more than double the wear of two days with a break in between. For that reason alone you should have more than one pair of black dress shoes. Possibly an Oxford or black brogue.
    In addition, you want a pair of waterproof shoes you can wear with a suit on a rainy day – unless you live in a dry climate. I’m not fond of the rubber soles or the less glossy shine, but I am very fond of dry toes on a rainy or snowy day. Get these in black and they could also serve as the second, less dressy pair of black shoes.
    And finally all those shade of brown but no tan shoes? Perfect in summer with s tan suit, or in the fall with a camel blazer. You might find these provide more variety than the brown monk straps.
    My choice five: dressy black, black brogue, waterproof black, brown brogue, tan. This does leave out the loafers, which is a loss, but you will find that lace-ups are actually better for feet!

  4. Simon says:

    Great article!

    I find I wear black shoes most of all. I found a pair that looked great and fitted perfectly so I went and bought a 2nd pair of the exact same shoe. I can alternate them and with proper repairs they will last me many years.

  5. Douglas Henderson says:

    Remember the guy who found a mint Yves St Laurent trench coat at Value Village for $8 cdn? C’est moi! I found a perfect pair of Moreschi black woven loafers for $9 Cdn reduced to $6 Cdn as I’m a senior-, again at Value Village– they were on sale in NYC at Shoe Mart for $650 US!

  6. Don Clarkin says:

    Are the suede and leather loafers shown at 5:16 in the video also acemarks? I don’t see them on the website and cannot even find a picture of them on google. If they are Acemarks, where can I buy a used pair and if not, what brand are they?

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