6 Types of Shoes Every Man Needs (And a Few Nice to Haves)17 min read

Shoes are important—perhaps, the most important item of clothing in a man’s wardrobe, which is why I’ve compiled this list of essential shoes for men. Besides nailing the fit, I’d say that most men should first start with investing in a few quality pairs of shoes.

Fellas, it’s time to take inventory of your current shoe collection; what you have and what you may need.

A Gentleman Within reader recently emailed me asking, what shoes every man should own. And so I thought about it.

Of course it’s up for debate, but as with any list of must haves, it comes down to your age, lifestyle or personal preference.

ESSENTIAL SHOES FOR MEN

So, let’s get to it. Here are what I believe are the 6 essential stylish shoes for men and a few extras for good measure.

^{Subscribe to the Gentleman Within YouTube channel.}

1. The Brown Brogue

What’s first up on the list of shoes every man should own? The brown brogue. It 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.

Where To Buy Brown Brogue Shoes

Quick Note: You might like this comparison between Beckett Simonon vs Allen Edmonds.

Mo’ Money No Problem

• AE Fifth Avenue Cap-Toe Oxford – $395 ($279.97 on sale)
• AE Strand Cap-Toe Oxford – $395 ($276.50 on sale)
• Grenson Burnished Leather Wingtips – $330

Ballin’ On A Budget

• Taft Beck Oxford – $275
• Beckett Simonon Yates Oxfords – $209
• Banana Republic Italian Leather Oxford – $158 (30% off at checkout)
• Ted Baker London Classic Brogues – $185

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.

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

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.

Where To Buy Men’s Chukka Boots

Mo’ Money No Problem

• Frye Bowery Chukkas – $328
• Mr. P Split-Toe Suede Chukka Sneaker – $365
• Edward Green Banbury Suede Chukkas – $1,530

Ballin’ On A Budget

• Astorflex Greenflex Chukka – $195 
• Astorflex Ettoflex Chukka – $180 ($126 on sale)
• Astorflex Greenflex Rough Chukka – $175 ($114 on sale)
• Auburn Suede Chukka – $69.97
• Clarks Bushacre 2 Chukka – $60
• Clarks Suede Desert Boot – $119
• Thursday Scout Chukka Boot – $149

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.

Quick Note: You might like this long term Clarks Desert Boots Review.

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

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.

Where To Buy Men’s Loafers

Quick Note: You might like this review of Jay Butler loafers.

Mo’ Money No Problem

• Mulo Suede Loafers  – $225
• Yuketen Bit Loafer – $340 ($255 on sale)
• J.Crew Camden Loafers – $148 ($118 on sale)
• Jay Butler Loafers – $195
• Ace Marks Penny Loafer – $299

Ballin’ On A Budget

• Stacy Adams Tassel Loafer – $89
• Auburn Suede Chukka – $69.97
• Thursday Handsewn Loafer – $145
• Cole Haan Penny Loafer – $99
• Florsheim Penny Loafer – $75
• Frye Penny Loafer – $100

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.

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

Quick note: If you’re enjoying this article on men’s fashion trends then you’ll probably like this article on men’s sneaker trends too.

4. The Minimalist Sneaker

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.

Where To Buy Men’s Minimalist Sneakers

Quick Note: You might like this long term review of Ace Marks Duke Sneaker.

• Greats Royale Sneaker – $179
• New Republic Leather Sneaker – $98
• Koio Capri Sneaker – $268
• Adidas Stan Smith Sneaker – $75-85
• Veja Esplar Sneaker – $120
• Vans Canvas Sneaker – $60 ($48 on sale)
• SeeVees Plimsolls – $73
• Beckett Simonon –  $250 ($179 on sale)
• Nisolo Diego Low-Top Sneaker – $150

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. It goes without saying, but minimalist sneakers in leather, suede or canvas will always be in style.

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

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.

Where To Buy Men’s Oxfords Or Derbies

Mo’ Money No Problem

• John Lobb Oxfords – $1,230-1,965
• Scarosso Oxfords – $320
• Paul Evans Cap Toe Oxford – $425
• AE Plain-Toe Oxford – $395

Ballin’ On A Budget

 

 

• Amberjack Original Derby Shoes – $179
• Beckett Simonon Oxfords – $350 ($209 on sale)
• Idrese Oxfords – $400 ($335 on sale)

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.

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

Rounding out the top 6 essential stylish shoes for men is the brown leather boot. 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.

Where To Buy Men’s Leather Boots

Quick Note: You might like this long term review of Thursday Boots.

Mo’ Money No Problem

• Idrese – $450 ($332 on sale)
• Red Wing Iron Ranger Boot – $330
• Red Wing Moc-Toe Boot – $278
• Chippewa Service Utility Boot – $280
• Wolverine 1000 Mile Cap-Toe Boot – $385
• AE Wingtip Dress Boot – $475 ($332 on sale)

Ballin’ On A Budget

• Thursday Cap Toe Boot – $200
• Thursday Full Grain Wingtip Boot – $235
• Aldo Lace Up Boot – $165
• Aldo Chukka Boot – $140
• Taft Cap-Toe Boot – $295
• Beckett Simonon Cap Toe Boot – $400 ($239 on sale)
• Idrese Chukka Boot – $420 ($335 on sale)

Did you know that many heritage brand boots like Red Wing, Thorogood 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 1000 Mile.

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.

Quick note: If you’re enjoying this article on must have shoes for men, then you’ll probably find my other writing on all things men’s style useful. Each week, I share updates, style tips and other things not shared on the blog through my free email newsletter.

To join now, just enter your email address below and click “Get Updates!”

STYLISH SHOES FOR MEN NICE TO HAVES

7. The Monkstrap Shoe

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.

Where To Buy Men’s Monkstrap Shoes

Quick Note: You might like this in-depth comparison of Cole Haan vs Beckett Simonon.

Mo’ Money No Problem

• Mr. P Single Monk Strap Shoe – $635
• AE Double Monk Strap Shoes – $395 ($256 on sale)

Ballin’ On A Budget

• Taft Double Monkstrap Shoes – $275
• Beckett Simonon Monkstrap Shoes – $350 ($239 on sale)
• Suitsupply Double Monk Straps – $249

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.

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.

8. The Chelsea Boot

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.

Where To Buy Men’s Chelsea Boots

Mo’ Money No Problem

• Common Projects Suede Chelseas – $525
• Paul Evans Chelsea Boots – $475
• Clarks Originals Suede Chelseas – $235

Ballin’ On A Budget

• Asos Design Suede Chelseas – $40
• Taft Chelsea Boots – $295
• Thursday Chelsea Boot – $199
• Aldo Chelsea Boots – $165
• Cestfini Suede Chelseas – $49.90

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.

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.

9. The Casual Sneaker

Last, but not least, the good ol’ casual running sneaks rounds out this list of essential shoes for men and nice to haves. Though not necessarily for running these days, these shoes are prime for more casual outfits and the trendy athleisure look. Check out this Nike Internationalist Review to see how I styled this popular running shoe.

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

Where To Buy Men’s Casual Sneakers

Quick Note: You might like this feature of J.Crew’s Nike Killshot 2.

• Allbirds Wool Runners – $98
• Common Projects Achilles Low Sneaker – $425
• Greats Royale Sneakers – $179
• New Republic Sneaker – $98
• Koio Capri Sneakers – $268
• Adidas Stan Smith Sneaker – $75-85
• Veja Esplar Sneakers – $120

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.

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

What Socks To Wear With Your Shoes

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.

Related: You might like this comprehensive Dress Socks Guide for men.

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.

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

Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.