6 Types of Shoes Every Man Needs (And a Few Nice to Haves)

Shoes are important—dare I say, the most important item of clothing in a man’s wardrobe. We spend countless hours wearing them, so it’s good to take inventory of our current collection; what we have and what we may need.

Besides nailing the fit, I’d say that most men should first start with investing in a few quality pairs of shoes.

Types Of Shoes Every Man Needs | Gentleman Within

A Gentleman Within reader recently emailed me asking, what shoes a man should have in his wardrobe. And so I thought about it.

Of course it’s up for debate, and every style blogger has a similar list with some variation. As with any list of must haves, it comes down to your age, lifestyle or personal preference.

So, let’s get to it. Here are the 6 essential shoe types I believe every man needs and a few extras for good measure.

1: The Brown Brogue

Brown Brogue Inspiration
credit: Pinterest

The brown brogue will quickly become a staple in any man’s wardrobe. It’s as versatile as it is stylish. Ready for this? The term “brogue” is derived from bro, the Gaelic word for shoe. Brogues are characterized by the unique punching or decorative perforations along the shoe’s leather uppers.

Did you know that brogues were originally added to leather shoes to serve as drains for muddy water?

I recommend a semi or quarter-brogue in a dark brown for your first pair. If you’re feeling sartorially inclined, go for a full-brogue (wingtip) in a tan/cognac shade. Keep in mind a pair like this is sure to turn heads, so if you’re not that comfortable with the attention, stick with a darker brown with minimal broguing. This will ease yourself into the wonderful world of brogues and give you limitless options to pair with jeans, chinos or wool trousers.

Mo’ Money No Problem

Brown Brogues Expensive
Fifth Avenue Cap-Toe Oxfords: Allen Edmonds | Strand Cap-Toe Oxfords: Allen Edmonds | Grenson Leather Wingtips: Mr. Porter

Ballin’ On A Budget

Brown Brogues Budget
Giraldo Wingtips: Cole Haan | Meliot Derby: Aldo | Aalian Suede Oxford: Aldo

The bottom line:
The brown brogue is a cornerstone of the smart casual wardrobe. It can dress up a pair of well-fitting jeans or dress down a tailored suit—serving you well, day or night, from the office to the dance floor.

2: The Suede Chukka

Suede Chukka Inspiration
credit: Pinterest

Surprised it’s number two on the list? There’s a good reason why.

Though not as dressy as brogues in the formality spectrum, it does land above the sneaker. It’s been said that the chukka boot is the first dress-casual shoe, which allows for tremendous versatility. Chukkas can play nicely with a suit, and can easily be worn casual with dark wash denim and a white t-shirt.

The chukka is a simple shoe with open lacing and two or three pairs of eyelets. You’ll typically find this ankle-high boot in suede or leather.

Did you know that a form of chukka, popularized as the desert boot, has its origins in the British military? Because of its comfortability and durability in harsh desert conditions, chukkas became many soldiers’ leisurewear of choice.

The ubiquitous Clark’s Originals desert boot is a go-to for starters. My suggestion is a suede pair, as the texture adds visual interest and a rich elegance to your look. As for colors—chukkas come in mostly neutral shades of brown and navy. Opt for a darker brown for more elegance and versatility or a lighter shade for more casual get-ups.

Mo’ Money No Problem

Suede Chukkas Expensive
Grenson Suede Chukka Boot: Mr. Porter

Ballin’ On A Budget

Suede Chukkas Budget
Fudge Suede Desert Boot: Clarks | Suede Desert Boot: h&m | Barret Chukka Boot: Nordstrom

The bottom line:
Chukka boots straddle the fence between dressy and casual—leaning more so on the casual side. Suits become effortlessly cool with chukkas and your casual options are limitless.

3: The Brown Loafer

Loafers Inspiration
credit: Pinterest

Casual, comfortable, cool. Dress them up, dress them down. Loafers are your summer go-to. Heck who says you can’t wear them year round?

Similar to the brogue and the chukka, loafers work with both formal and casual outfits. This kind of versatility has the loafer sliding in to my top 3.

Though not recommended to wear with a full on suit, loafers look great paired with a sport coat and denim or chinos. You can go suede or leather here. Penny or tassel—your pick. Another great option is the horsebit Gucci loafer of Italian origins, distinguished by the metal strap across the front. It will surely add a dash of sophistication to your look.

Did you know that tassel loafers originate from the same design found today in boat shoes?

Less formal than lace-ups, the loafer comes in a myriad of colors of black, navy, and even green or red for the bold. I suggest a brown pair for maximum versatility. Leather or suede, it’s up to you.

Mo’ Money No Problem

Brown Loafers Expensive
Lewis Penny Loafer: Frye | Tod’s Suede Loafer: Mr. Porter | Acheson Tassel Loafer: Allen Edmonds

Ballin’ On A Budget

Brown Loafers Budget
Kenton Suede Penny Loafer: J.Crew | Pinch Grand Tassel Loafer: Cole Haan | Oval Driving Shoe: Florsheim

The bottom line:
Loafers are a summertime staple. The classic weekend shoe that’s comfortable, easy to slip on, and super stylish.

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4: The Canvas Sneaker

Canvas Sneakers Inspiration
credit: Pinterest

Sometimes even the most dapper of men like to go casual. And with the casual aesthetic popular as ever, it’s good to have a go-to casual footwear option. The canvas sneaker is great for all types of casual outings from ballgames to backyard BBQs.

Did you know that the original canvas sneaker (Keds) was born in 1892 by the U.S. Rubber Company? It’s been said the word “sneaker” became popularized by an advertising campaign. The shoe’s rubber sole was so quiet, you could sneak up behind unsuspecting people.

I suggest going for a pair in a neutral shade of beige, white or gray. That way you won’t have to think too much about what to wear them with.

Canvas Sneakers
Salt Washed Sperrys: Sperry Top-Sider | Vans Washed Canvas Sneaker: J.Crew | Hermosa Plimsolls: SeaVees

The bottom line:
The canvas sneaker is stylish, versatile and a great flip-flop alternative. It’s the summertime go-to for when you’re keeping it really casual.

5: The Oxford or Derby

Oxford Derby Inspiration
credit: Pinterest

The obligatory Oxford or Derby (also called blucher) rounds out my top 5. A black Oxford or Derby is typically the first formal pair of shoes a guy owns. I know mine was. But it was of the square-toed variety which I do not suggest. I recommend a more classic rounded toe Oxford or Derby.

You may be wondering what’s the difference between the two. In short, Oxfords have closed lacing whereas Derbys have open lacing. As for which is more formal—the Oxford. Here’s an article showing in detail, the difference between them if you’re curious.

Did you know that the Oxford is named after Oxford University in the UK? Before this, the Oxford has its origins in Scotland and Ireland, also known as Balmorals.

I recommend a quality pair of Oxfords. The two main factors that comprise a quality shoe are price and make.

A good pair of welted leather shoes goes for around $360. Seems pricey, but investing in a quality pair will last for decades. Brands that have been around for 20 or more years are reputable. Some have stood the test of time for over a hundred years.

Brands to know:

  • Church’s
  • Allen Edmonds
  • Aldens
  • Tricker’s
  • Foster & Son
  • Edward Green
  • John Lobb

As for color, I would go black or brown here. Black of course is appropriate for the most formal of occasions; think funerals, weddings, and black tie events. Brown is more casual and versatile. The lighter the shade the more casual. A nice cap-toe Oxford or Derby is my recommendation for a first dress shoe.

Mo’ Money No Problem

Oxford Derby Expensive
John Lobb Oxford: Mr. Porter | Church’s Oxford: Farfetch | Cagney Cap-Toe Oxford: Paul Evans | Carlyle Plain-Toe Oxford: Allen Edmonds

Ballin’ On A Budget

Oxford Derby Budget
Troiwet Oxford: Aldo | Rickmann Derby: Aldo | Craosa Oxford: Aldo

The bottom line:
The Oxford and Derby are men’s style essentials. They’re sleek, they’re dressy, and separate the men from the boys.

6: The Brown Leather Boot (lace-up)

Brown Leather Boot Inspiration
credit: Pinterest

A brown pair of leather boots makes the cut, and for good reason.

Depending on the style, you can easily add a bit of sartorial sophistication or rebellious ruggedness to your look. You’ve got dress boots, casual work boots, chukkas, chelsea boots, and even cowboy boots.

Did you know that many heritage brand boots like Red Wing and Wolverine have been around for well over a hundred years?

You can opt for a more casual work boot or stylish dress boot depending on whichever your preference is. Whatever the case, there’s a certain character about a well-worn pair of boots. Some guys go as far as to intentionally beat the hell out of their boots just for that much desired worn in look.

I recommend (you guessed it) a brown pair because they go nicely with dark wash denim, corduroy, chinos or wool trousers. I personally like to cuff my jeans for a bit of casual flair whenever wearing a pair of rugged boots like the Wolverine’s 1000 Miles.

Mo’ Money No Problem

Brown Boots Expensive
First Avenue Dress Boot: Allen Edmonds | Dalton Wingtip Dress Boot: Allen Edmonds | Red Wing Moc-Toe Boot: Zappos

Ballin’ On A Budget

Brown Boots Budget
Captain Boot: Thursday | Etausen Boot: Aldo | Stafford Deacon Wingtip: JCPenney

The bottom line:
Brown leather lace-ups are utilitarian, but still look great. The perfect fall/winter shoe option. Dress them up, dress them down, wear them into the ground. Clean ’em and do it all over again.

A Few Quick Things About Socks

Our reader also asked about how to wear socks with shoes, and so I wanted to quickly address a few things.

It’s my opinion that no color of sock is right or wrong. What matters is the combination of colors you choose. When it comes to socks, the things to pay attention to are color, pattern and fabric. If you want to play on the safe side, you can’t go wrong with navy, burgundy, dark gray or dark brown socks. These go particularly well with darker colored shoes.

As a rule of thumb, you want your socks to be just as dark as your shoes, but also keep them close in shade to the color of your pants. And finally, don’t just think about harmonizing with the color of your shoes and pants, but all of the other articles of clothing you’re wearing as well.

Lastly—if you’d like, disregard what was said above, and go f’in crazy. Have fun with your socks as it’s a great way to add personality to your outfit.

The bottom line:
For detailed insight on how to wear socks, ties.com has this great guide to men’s sock fashion.

The Nice To Haves

The Monkstrap

Monkstrap Inspiration
credit: Pinterest

Technically the monkstrap is a loafer because it has no laces, you just slip them on. It comes as a single strap, double strap and even triple straps, with the double being the most popular. It’s either you love them or you hate them. I view the monkstrap as a grown man’s velcro sneakers.

Did you know that the name comes from an era in Europe when monks used to wear shoes with a buckle as an alternative to sandals?

They’re not for everybody, but many stylish men have at least one pair of double monks in their wardrobe. Wear them with pants that have no break (pants cuff just barely skims the shoe) giving the shoe and buckles the spotlight.

Mo’ Money No Problem

Monkstrap Expensive
Single Monk Strap: Suit Supply | St. John’s Double Monk Strap: Allen Edmonds | George Cleverley Double Monk Strap: Mr. Porter

Ballin’ On A Budget

Monkstrap Budget
Williams Single Monk Strap: Cole Haan | Conard Double Monk Strap: Johnston & Murphy | Madison Double Monk Strap: Cole Haan

The bottom line:
The monkstrap is an ultra stylish shoe that can be worn formal with a suit or more casually with jeans and a blazer.

The Chelsea

Chelsea Boot Inspiration
credit: Pinterest

The chelsea boot is popular as ever. It’s iconic in its design, but the chelsea is not for everybody. I personally disliked the style for the longest time, but recently came around after realizing they look really good with jeans and chinos. They can also be worn with suits.

Did you know that the chelsea boot has Victorian roots and has been around for over 150 years?

Chelseas come in a variety of colors and you can’t go wrong with suede or leather.

Mo’ Money No Problem

Chelsea Expensive
Frye Chelsea Boot: Frye | Suede Chelsea Boot: Suit Supply | The Dean Chelsea Boot: Paul Evans

Ballin’ On A Budget

Chelsea Budget
Duke Chelsea Boot: Thursday Boots | Vianello Chelsea Boot: Aldo | Suede Chelsea Boot: Urban Outfitters

The bottom line:
The simple and clean silhouette of the chelsea boot lends itself to many different styles of dress; formal or casual, take your pick.

The Casual Sneaker

Running Sneakers Inspiration
credit: J.Crew

Last, but not least, the good ol’ casual running sneaks. Though not necessarily for running these days, these shoes are prime for more casual outfits and the trendy athleisure look.

Whether you’ve got some errands to run or some buddies to meet up with, the casual sneaker is the most comfortable option you’ve got. Rock them with joggers and a ball cap or rolled up jeans and a blazer.

Did you know that the sneaker, originally called plimsolls, dates back to the late 1700s? During this time there was no difference between the left and right shoe, believe it or not.

I recommend a pair with neutral shades, though you can opt for a pair with a pop of color here and there as well. No harm done.

Running Sneakers
Onitsuka Tiger Sneakers: J.Crew | New Balance Sneakers: J.Crew | Classic Sneaker: Reebok | Internationalist Sneaker: Nike

The bottom line:
Casual sneakers feel great, and the right pair can make for a stylish, laid back type of vibe.

In Closing

A good outfit and good shoes must always go together, you shouldn’t have one without the other. 

I hope this was helpful in illustrating why these shoes made my list of essential shoes for men.

Men's Shoe Essentials | Gentleman Within
A summary of Gentleman Within’s list of shoe essentials for men

On to you. This is just one man’s opinion…what’s on your list of essential men’s shoes?

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