Dress Shoes Every Grown Man Should Own

There comes a time in every man’s life when he has to put aside his kiddy wardrobe for something a little more “grown up.”  The older one gets, the more one is expected to attend events that require varying levels of formality and you certainly don’t want to meet a potential employer, investor, or mentor in a beat-up pair of shoes - which is why I am here to help!  If you are looking to replace your cheaper shoes with investment staples, or build out your dress shoe wardrobe from scratch, my list below will help you get started.

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Black Cap-Toe Oxford

The black cap-toe Oxford is what I like to call a “work-horse” shoe.  This is a shoe that you can wear to almost every occasion where a jacket of some sort is required.  From weddings, to funerals, job interviews, business dinners or even black-tie optional events, the black cap-toe Oxford is always appropriate.  Because of this, I recommend it as the first shoe you invest in when building out your dress shoe wardrobe.  And as you will get so much wear out of it, go for the highest quality shoe you can afford; I went for a very classic pair by Paul Stuart.

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Brown Lace-Up 

Once you have black down, the next shoe you should go for is another lace-up, but in brown.  Some might say you should stick with leather, but personally I think suede could be a great option as well (I personally like both).  For your brown pair, feel free to have a LITTLE (and I mean a little) more fun by purchasing a pair that features SOME broguing details (i.e. the little dots that sometime form a pattern on the tip of the shoe).  My wardrobe consists of a brown calf leather lace-up by Paul Stuart (seen below), and a suede version by London bespoke shoemakers George Cleverly.

Slip-On Loafer

To switch it up a bit, consider a slip-on loafer for your third addition.  Personally, I would go for a dark brown suede option that can easily transition from day-to-night (but if you prefer leather that also works).  The great thing about most loafers is that, unlike Oxfords or other lace-up styles, they go great with jeans as well as suits.  I have a few versions of the loafer across different price points, but my “investment” version is from Spanish shoemaker Carmina.  If you need to go a step down in price, I would also recommend one of my favorite menswear brands, Suitsupply, which has a great selection of loafers as well.

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Monk Strap

If you are attending an event that requires a suit but is not extremely conservative, monk straps are a great alternative to lace-up dress shoes, and my fourth recommendation for your collection.  Whether you are drawn to double or single strap version, monks have the ability to style up any boring suit.  While I usually advise shooting for the top of your budget to get the best quality shoe possible, I find that men don’t wear monk straps as often as some of their other options.  Because of this, if you have to choose where to spend your money, I would cut here and invest in one of the previous pairs I mentioned.  For example, I really wanted a monk strap look but did not want to spend a ton, so I actually bought a suede pair from Suitsupply that have held up nicely. 

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Chelsea Boot

Ahhh the Chelsea boot; a shoe I’ve historically had a complicated relationship with but have since grown to appreciate (and eventually own a few pairs of lol).  Chelsea boots are another “work-horse” shoe, and throughout my journey with these shoes I have discovered they really can (depending on the version) go with everything (I have even worn a pair of Chelsea’s with a velvet dinner jacket, turtleneck and tuxedo pants and it was FIRE).  Despite the shoe’s versatility, it is still a boot and is not always weather appropriate, so I am putting this style at number five on the list.  I also don’t think you necessarily have to go with the most expensive option there is. Frankly, a lot of Chelsea boots across price points look very similar.  On the high end I personally own a few Saint Laurent pairs which I love.  If you want to be more conservative with your spending, Asos has a good range of options to choose from. 

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Velvet Slipper

To round out your grown man dress shoe wardrobe, I recommend investing in a good velvet slipper.  Now you might be saying to yourself, “I don’t go to that many evening events; would I get my money’s worth?”  I am here to tell you, YES!  While velvet slippers are great with tuxedos and evening-wear, they also can style up suits for dressier evening events that aren’t black-tie, and I’ve even worn them with jeans and a t-shirt.  I personally love velvet slippers and have a few pairs, but the classic all black version by Del Toro is a great version to start with and is a staple in my collection.

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