The 5 Types of Shoes All Guys Must Have

Dave Bowden

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Must Have Shoes for Men Shoes are the secret weapons of a man’s wardrobe.

One of the first things women notice about you, the right pair can elevate your entire look, and instantly make you look more polished and put together.

The wrong pair, meanwhile, can have the opposite effect. Even your best suit won’t look quite right if you’ve got a ratty pair of shoes strapped to your feet—or even just one that’s inappropriate to the occasion.

There are almost as many styles of shoes as there are stars in the sky, but fortunately you don’t actually need a whole closet full of kicks.

Focus on the five must-have shoes listed here to make sure you’ve got your bases covered. You can expand your collection after that, starting with a few of the “good to have” options below.

Must Have Shoes for Men

5 Must Have Shoes for Men

1. Wingtips

Must Have Shoes for Men Also called “brogues,” wingtips are among the most versatile (and thus, often the most worn) shoes in any man’s wardrobe.

One of the biggest benefits of wingtips is how perfectly they skirt the line between “dressy” and casual. A sleeker pair with a well shaped toe can work just fine with a business or wedding suit, while a thick-soled pair can help take a basic sweater-and-jeans outfit next level.

A few good options:

Florsheim Men’s Montinaro Wingtip Oxford
Clarks Men’s Montacute Wing Oxford Shoe
Bostonian Men’s Melshire Wing Lace Up Dress Oxford

2. “Dress Shoes”

Must Have Shoes for Men That’s not a technical term, of course, but there are numerous shoe styles that are formal or “dressy” enough to wear on occasions that call for a suit, like weddings, funerals or job interviews.

As mentioned above, some brogues could be considered dress shoes, but generally speaking dress shoes are sharper and have a more pointed toe (just don’t go too pointy — you want to look refined, not like the genie in Aladdin).

In addition to the sharper shape, dress shoes tend to have fewer bells and whistles, like a thin outsole/welt and neutral laces and eyelets. As a rule of thumb, the sleeker a shoe looks, the dressier it is.

Pro Tip:

Keep in mind that dress shoes aren’t just for wearing with suits. Throw a pair on when you’re just rocking chinos and your favorite polo to instantly take your look from casual to “smart casual.”

A few good options:

Stacy Adams Men’s Dickinson Cap-Toe Oxford
Bruno MARC PRINCE Men’s Modern Classic
Calvin Klein Men’s Carwin Box Smooth Oxford

3. Boat Shoes or Loafers

Must Have Shoes for Men Maybe the most classic warm weather staple of all time, the boat shoe evokes thoughts of John F. Kennedy effortlessly rocking a pair of Ray Ban wayfarers and sailing off the shore of Nantucket. Loafers, meanwhile, give you a similarly laid back (though admittedly more landlocked) vibe.

When you need something more casual than brogues but a little more grown up than sneakers, boat shoes or a comfortable pair of leather loafers are the perfect choice.

A few good options (Boat shoes):

Sperry Top-Sider Men’s A/O Boat Shoe
Dockers Men’s Vargas Traditional Boat Shoe

A few good options (Loafers):

IZOD Men’s Edmund Penny Loafer

4. Sneakers

Must Have Shoes for Men Whether you’re running a few quick errands or just out having a casual drink with friends, sometimes you just want to wear sneakers, you know?

Sneakers long ago developed a culture unto themselves, and it’s pretty easy to find yourself intimidated or overwhelmed by the sheer volume and variety of shoes on the market.

Fortunately, they’re also a pretty easy pair of shoes to nail. Just keep it simple and look for one classic color (white, black, grey and blue are always safe choices), few labels, and a bit of contrast coming from the sole, laces, eyelets or all of the above.

A few good options:

Airwalk Men’s Legacee Sneaker
adidas Performance Men’s Baseline
PF Flyers Men’s Center Lo Fashion

5. Desert Boots/Chukkas

Must Have Shoes for Men When the weather gets too cold for your boat shoes or loafers, swap them out in favor desert boots or chukkas. The preferred footwear of everyone from Steve McQueen to James Bond, these boots scream “casual but classy.” F

rom about September to December, and then again from March to May, you could easily go weeks without having to wear a different kind of shoe (and I have to admit I sometimes do).

Clark’s offers one of the most classic, can’t miss pairs, as does Johnston & Murphy, but I prefer a style with a slightly sharper toe shape, like the ones pictured here from Alberto Fellini.

A few good options:

Clarks Men’s Bushacre 2 Desert Boot
Alberto Fellini Classic Chukka Desert Oxfords
London Fog Mens Broadstreet Chukka Boot

And a Few More “Good-to-Haves”:

Must Have Shoes for Men
Suede Bucks or Brogues

Falling somewhere in between leather wingtips/brogues and boat shoes/loafers, suede shoes are a great way to stand out and add a little flair to your look, without going full peacock.


Must Have Shoes for Men Double Monk Straps

Double-monks came back hard a few years ago and haven’t gone away. Named for the small buckles they use in lieu of traditional laces, monk straps tend to look a little more stylish and refined.

Must Have Shoes for Men “Dressy Boots”

Chukkas are great, but you can’t really wear them with a suit or a more formal outfit. If you work in a formal office or frequently find yourself wearing a suit in cold-weather climates, you might want to consider a pair of boots that have the refined leather and sleek toe shape of a dress shoe, but run all the way up to your ankles.

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8 thoughts on “The 5 Types of Shoes All Guys Must Have”

  1. Hi Dave, any picks for a dressier loafer? I want a slip-on shoe I could wear to work (my office is business/business casual attire.)

    • Hey Benjamin. I’ve got a pair of Stratton penny loafers from Johnston & Murphy. They’re great – perfect toe shape (in my humble opinion), clean lines and good quality leather. I wore them with a suit to a wedding this summer and they worked perfectly. Should be more than appropriate for the office!

    • Hey Diego! This is the stylish man’s ongoing dilemma. I definitely feel your pain, especially being based here in Canada, where there’s snow, salt or mud on the ground for about 60% of the year. I’ve found the best (and most affordable) way to take care of your shoes is to do it yourself. Invest in a good shoe care kit like this one, set aside some time each week, and make a habit of polishing your shoes. I find if I throw a podcast in and kind of lose myself in what I’m doing, it can actually be a really relaxing, almost cathartic experience.

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