6 Shoes Every Man Should Own

These are the shoes that I recommend to my clients when we first start working together and they want shoes that will work for most occasions they'll encounter throughout the year.

Use this as a general starting point and feel free to add additional shoes after you've identified the gaps in your wardrobe.


These shoes will get you through an entire year, for all occasions. Some you may not need, so just omit them.

Low-Top Sneakers

Why You Need Them

Low-top sneakers look great with casual, and even dressy-casual outfits and, if chosen correctly, they can make your everyday looks pop with a touch of class. I’d consider them to be absolutely essential to any well-dressed man’s wardrobe.

Mistakes To Avoid

  • High-top sneakers

  • Chunky or bulbous designs

  • 'Dress' sneakers - dress upper with sneaker sole.

  • Not cleaning them

  • Not tucking the shoelaces

  • Statement sneakers - loud, flashy designs.


  • Leather

    This is not only the best-looking material, but it is also the easiest to keep clean and it works for year-round wear. Leather alternatives are also great.

  • Canvas

    Not as stylish as leather but definitely cheaper and has the same basic look. However, it will stain easily and will be much harder to clean.



  • White low tops look cleanest and will go with every single outfit, now and forever.

  • white is too bright or draws attention to your feet, it's all in your head - I promise.


  • If, and only if, you just can't do white, grab a pair in gray and still grab a pair in white.

  • Gray is the most versatile color (outside of white).

    • Once you're comfortable wearing gray, start wearing the white ones. 

  • Black and navy are too dark of a color and don't pair with as many outfits so they would be a very distant 3rd and 4th color to get.

Want to see my favorite brands for each of these shoes as well as how to put together great outfits for each? Check out my Essential Capsule Wardrobe App.

Athletic/Running Shoes

Why You Need Them

These shoes can pull double duty of being stylish and looking great in sporty casual or elevated casual outfits and also be functional workout shoes.

Go for something with a sleek profile so it's not so imposing in your outfits. If you have the budget or your workouts are especially hard on shoes, consider having casual running/athletic sneakers separate from your gym or exercise pairs.

Mistakes To Avoid

  • Big, chunky designs and profiles

  • Using the wrong shoes for your workout.

  • Bold colors and designs

  • Pairing with white socks

  • Cheaping out


  • The material is up to you.

  • Woven uppers provide breathability but can leave your socks and feet wet in inclimate weather.

  • There are also suede, leather, or other synthetic materials. Leather is easiest to keep clean, especially in lighter colors like white and gray.

  • Pick the materials that make sense for your climate and usage.


I recommend sticking with a black/white, black/grey/white, or navy/white/color to ensure that your sneakers complement all your outfits.

Other crazy colors like neon green or a bright red will only draw attention away from your outfit which is why I’m not recommending them, but that's only if you want to look your best when working out. If you don't care, then go nuts.

Lace-Up Boots

Why You Need Them

OK, I know these are boots, not shoes, but I honestly feel that every man needs a pair of these bad boys in his closet.

The lace-up boot has been around forever and adds a masculine touch to any outfit which is why they're an absolute essential.

The problem most guys have is that there are many options and they can't be worn year-round depending on your climate, so it gets confusing quickly.

I recommend going for a casual boot, rather than a dress boot as this is the most versatile style. Dress boots aren't as versatile because only work with more formal outfits.

Mistakes To Avoid

  • Choosing the wrong type of boot for your body type.

  • Cheap materials

  • Not conditioning for bad weather.

  • Bold colors and contrasting stitching



  • Leather

    This is the classic material for year-round wear. Make sure to go for real leather, which may be pricey but it will last so much longer than synthetic fabrics.

  • Suede

    Has a textured effect that works particularly well during the fall. However, it is not as durable as leather and can easily be ruined by wet weather.


  • If you live in a climate with more severe weather, go for a rubber lugged or dainite sole which provides greater traction, particularly in wet weather.

  • A normal dress boot has smooth leather on the bottom and you will slip and slide in wet weather.


Dark Brown

  • This is the most versatile color you can choose and it will pretty much go with everything in your essential wardrobe.

  • If you had to only have one boot, I'd say this brown pair would be it for maximum versatility.


  • Lace-up boots in a classic black shade look extremely cool and timeless.

  • However, keep in mind they can only be paired with gray, black or navy pants.

Want to learn more about the other accessories you should own to level up your style? Check out my Essential Capsule Wardrobe App.

Oxford Dress Shoes

Why You Need Them

These are the best men's dress shoes, no questions asked. When you imagine a well-dressed man in a suit, he’s wearing a pair of these, and everything else pales in comparison. 

Not only are they one of the most versatile dress shoes a guy can own – which will work for nearly all formal occasions from business casual to formal – but they’re the de-facto standard shoes to wear with a suit.

Mistakes To Avoid

  • Thinking black & brown dress shoes = Oxfords.

  • Too shiny

  • Bold colors (including laces).

  • Incorrect shade of brown.

  • "Dress" Sneakers


Though Oxfords come in a variety of different materials, stick with leather or a leather alternative, as this is not only the most stylish, classic material but also the easiest to wear and looks best all around.

I prefer plain toe, but you can also get cap toes, but I will grab a pair of plain-toed Oxfords or Derbys over any other kind of dress shoe 99% of the time.



  • This works well with any black or gray business casual, dressy casual, or formal items in your wardrobe.

  • It can also be used with darker navy blue, but don't pair it with lighter blue colors - it is too dark relative to those colors.


  • This works well with gray, navy, and brown pants/suits.

  • Medium brown - not light brown (tan) or dark brown (closer to black) - is most versatile.

  • Beware of brand color names, they're all over the map, so look for this color visually instead of going based on what they call it.

As for brogueing, burnished toes, oxblood, or other unique colors, don’t get me wrong, I love them, but that’s like two levels down the road if you’re new to dressing better. They’re very specific and won’t go with a lot of your outfits, so grab them after you’ve invested in a classic black and dark brown Oxford.

Chukka Boots

Why You Need Them

OK, I had to throw one more pair of boots in here!

Chukka boots are light and versatile ankle boots that hit the sweet spot between a heavy lace-up boot and a sneaker.

They have the power to elevate all kinds of outfits, and one of the best things about them is that they work especially well with your body type.

They’re a great option for the spring and fall, and, if chosen in the right color and material, can also work throughout the summer and winter months.

Mistakes To Avoid

  • Cheap materials

  • Not conditioning for bad weather.

  • Pairing with suits

  • Bold colors, contrast stitching, or contrasting sole colors


  • Leather

    This is great for year-round wear, particularly in a medium brown shade.

  • Suede

    This is a more casual fabric but it looks especially great during the spring, summer, and fall months, as it adds just a bit of texture to your overall look. However, if you live somewhere with a lot of snow or rain, you should avoid wearing them during that time, as the material will get ruined.


Medium Brown

  • Grab a medium brown pair in leather because it goes with everything but black pants

  • Avoid tan, oxblood, or dark brown as they're not as versatile.


  • A black pair of Chukkas in either leather or suede would also be a great choice.

  • These will look great with dark-wash jeans and any gray or black pants you own.

Penny Loafers

Why You Need Them

Of all the members of the loafer family, the penny loafer is the classiest and most versatile.

These stylish slip-ons are surprisingly easy to pair and can be dressed up with a suit or dressed down with everything from jeans and an Oxford dress shirt to chinos and polos.

As well as offering a feeling of instant polish to your outfits, their design allows your feet to breathe more than dress shoes, making them perfect for the warmer months or climates.

Mistakes To Avoid

  • Not wearing no-show socks

  • Bold or hard-to-wear colors

  • Wrong shape

  • Contrasting stitching

  • Ill-fitting - they should look like they were molded to your feet.


  • For your first pair of penny loafers, you always want to go for a pair in leather or a leather-like fabric over suede.

  • Leather penny loafers have an undeniably smart aesthetic that works with your dressier outfits and they also have the ability to dress up your more casual looks.

  • Also, leather is a very durable material and can age really well, if treated correctly.

  • Suede loafers should only be reserved for the spring and summer months.



  • Black leather penny loafers have an undeniably dressy aesthetic.

  • They work for business casual, smart casual, and formal dress codes.

  • They look particularly good when paired with black or gray items, as well as indigo denim.

  • Don't pair them with light blue items because the colors don't mesh well.

Medium Brown

  • Brown leather penny loafers will work when paired with both casual and elevated casual and business casual items.

  • They look particularly good with gray and navy items (like dark-wash jeans), as well as lighter colors like tan chino pants.

  • Remember to go for medium brown.

    • Darker and lighter shades aren't as versatile.

Want to learn what specific items you can wear with each of the shoes on this list? Check out my Essential Capsule Wardrobe App.

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