Men's Casual Shoe Guide: The Top 15 Essential Shoes (2024)

In a world with hundreds of shoe types, shopping can easily overwhelm. Whether shopping online or in a store, no one wants to feel like their next purchase is a needle-in-a-haystack away. The good news?

This casual shoe guide for men will simplify your search down to fifteen must-haves. Fill your closet with casual shoes for home, work, the beach, or wherever else your heart—and feet—desire.

Here, we’ll cover the following topics:
- What are casual shoes?
- Top 15 essential casual shoes for men
- Living fashion-forward

Ready to look your best?

In this society, casual is a culture. But what, exactly, does this mean?

In the fashion world, casual takes on different forms depending on the occasion. For example, a casual dress code for dinner on a boat may look different than that of a casual Friday night out. In this sense, casual is chameleonic.

Casual holds a wide spectrum of styles, from flip-flops to monk shoes to dress boots. Within each style of shoe, there’s also a spectrum that toggles from less casual to more casual. Your use for them may dictate how formal or informal a shoe truly is.

For example, for flip flops, camo pool shoes are incredibly informal, whereas brown Reefs work better for a casual summer lunch or dinner. Casual suggests, “appropriate but not black tie fancy,” so there’s room to play here.

Our best advice? Follow your intuition. If you’re still not sure, you can ask other attendees of the event, or ask the event host about the dress code. This is also why it helps to have multiple casual shoe options, which we’ll get into next.

Note that dressing casual can be subjective, held loosely, and changeable depending on your outfit. Ever hear the phrases, “dressing up” and “dressing down?” To dress down is to opt for a more casual look.

Whether you dress your outfits to match your shoes or vice versa, here are the top 15 essential casual shoes for men to keep in your closet for any occasion.

Sometimes, it’s easier to define casual by what you know it’s not. You can likely feel that patent leathers are fancier than casual leather sneakers casual leather sneakers, even if you don’t know why.

These 15 essential pairs of casual shoes for men are here to help you win when it comes to casual. Let’s get into it.

Typically made of leather or suede, penny loafers are a great casual shoe option for work meetings, social soirees, friend gatherings, and date nights. Classically, this style mirrors a slip-on (more on these later), with no lace and low heels.

May we suggest a classy BOSS for when you want to look (or feel) like one, a cool black Calvin Klein, or a multi-purpose Polo Ralph Lauren?

Oxford shoes are an absolute must for your wardrobe and here’s why. Beyond their effortless, spiffy look, they’re close-laced and come in three main styles: cap toe, wingtip, and plain toe.

Though seemingly small, these nuances evoke certain feelings. Perfect for an indoor or outdoor wedding, a first day of work, or a promotion-worthy presentation, these shoes are loyal, stylish, and fresh.

We suggest starting with a unique Florsheim, a cognac-colored Massimo Mateo, or a crisp Cole Haan.

Note that Zappos’ shoes are variable in size and color.

At first glance, it’s easy to associate brogues with the former two shoe types and for shoe novices, this wouldn’t be completely inaccurate. Brogues can be Oxfords and vice versa.

However, brogues are leather and low-heeled, notorious for their perforations around the edges. The term “broguing” stems from the Irish word, “bróg,” and signifies “leg covering” in Old Norse.

Brogues, like Oxfords, live on the higher end of casual. Try them out with a clean-cut suit, for book club, or a third date.

Look your best with the help of some Anthony Veer, a multi-colored PIKOLINOS, or a walnut-colored Allen Edmonds.

Derby shoes are most compared to the Oxford shoe, though they differ on one main detail: derby shoes are open laced and Oxford shoes have closed laces.

Derby shoes have a low heel and looser laces for heightened mobility and comfort.

For this look, we recommend an amber ECCO, , or a vegan leather Vance Co..

Chukka boots are ankle-high boots, often made from leather or suede. They can perfectly elevate a fresh pair of jeans for casual Tuesdays, sweater weather, or an outdoor family photoshoot.

Note that depending on the brand, the length of boot may vary slightly. We love a steel gray suede Rockport, a brandy-colored Nisolo, or a shadowed SeaVees.

Chelsea boots are a fantastic casual men’s shoe option. They hold a similar height to the Chukka boot, with the main distinction of an elastic side panel.

Chelsea boots are sleek and polished to pair with tighter fitting pants. Give them a go for your next hosting event, game night, axe throwing competition, or movie night out.

Why not give these lovable Blundstone, shining Frye, or highly-revered Dr. Marten a try?

So far, we’ve covered outside-the-home options, but what about shoes for the home? Casual spans across all contexts and moccasins are a perfect at-home comfort. Similar to slippers, use them to hug the feet at home, the cabin, or at a warm winter getaway.

Moccasins are a flat shoe that insulate all parts of the foot. For extra support, try out these gel-infused, memory foam Isotoner, cinnamon suede Minnetonka, or camel Anodyne.

Sandals can be open-toed or closed-toed, depending. They usually have an exposed heel, perfect for warm weather outings, vacation, or quick errands in town. If you use sandals in wet environments, just be sure they’re water-proof!

May we suggest some briar-brown Dockers, grizzly-leather UGG, or dark brown Kamik?

Espadrilles are a must for every man’s closet! They’re light and breathable, perfect for a summer meal, barbeque, or outdoor concert. Espadrilles are a flat shoe that covers the entire foot with a textured or colored pattern.

Not sure where to start? How about with some recycled cotton canvas TOMS, sunset Patara, or cream Soludos with beer graphics on them? It doesn’t get better than that.

Boat shoes are light, flat shoes made from leather or canvas, depending. Perfect for a day on the yacht, patio brunches, or rooftops, boat shoes aren’t limited to just boats! Pair them with a casual, beachy t-shirt or a breezy button-up.

Shoe-wise, why not try the java Dunham, amaretto Sperry, or charming Sebago?

Now, dress boots are on the more formal end of casual, but again, you can dress down to match the mood. Dress boots are the umbrella category for shoes like Chelsea and chukka boots. They all share similar higher-ankle lengths.

To optimize your boot flair, wear them with tighter-fitting pants to make them pop! Dress boots are a hit on the dance floor, cooler evenings out, or as fall-friendly wear.

Suggestions? Coffee-colored Steve Madden, pecan brown Penny Luck, or scorched SOREL.

Combat boots are great allies for jeans, dress shirts, leather jackets, and khakis alike. By nature, combat boots have an edgier look than most other boots, commonly found in black or darker colors.

Functionally, combat boots are known for their strength and stability and come with a defining style. Wear them out to the bar, on the mountains, or to combat a damp day.

Our go-tos? Forest-wood GINANNI, Original S.W.A.T., or the distinct Donald Pliner.

Slip-ons are made to…slip on! They’re the easiest functional shoe to wear in or out. Slip-ons are flat, easy, and multi-purpose, perfect for getting to and from, work, or a casual Thursday dinner.

Beyond flip-flops or sandals, casual slip-ons shoes have a distinct look—low-heeled, laceless, and comfy for everyday to-dos.

Rock the right slip-on with white Ben Sherman, gray, textured Deer Stags, or navy Original Penguin.

Flip-flops are easily misunderstood. While black tie and flip-flops don’t go hand-in-hand, in the right environment, flip-flops can rank supreme.

Likely one of the most casual shoe types for men, flip-flops are presentable and relaxed at once. Use them at the pool, for a drink by the creek, or a late night ice cream run.

The flip-flops on our mind? Tommy Hilfiger, a The North Face, or Cobian!

From this men’s casual shoe guide, you can start identifying your preferences and organize accordingly. If we were to make a business casual shoe guide from the aforementioned list, we’d choose the following (in no particular order) specifically for work-related attire:

- Penny loafers
- Oxford shoes
- Brogues
- Derby shoes
- Chukka boots
- Chelsea boots
- Dress boots

However, depending on company culture and etiquette, you might also include these casual shoes for men in the workplace:
- Espadrilles
- Combat boots
- Slip-ons
- Sneakers

There’s never just one shoe for one type of outing or occasion, so it’s best to equip your closet with several options that speak to you. As you grow your wardrobe and style, you’ll be able to know casual in a way that just works.

Our hope is that from this casual shoe guide for men, you feel the freedom to mix, match, and create exactly the way you wish to feel from the bottom, up. Check out Zappos to find options that leave you feeling priceless. Casual has never looked (or felt) so good.