I may own more pairs of shoes than my girlfriend.
OK, I don’t but it’s pretty close.
The thing is, as you get older it’s important to wear the right footwear for the occasion.
And it’s good to be ready because you never know what tomorrow’s going to bring.
Whether it’s a wedding invitation from your third cousin or an impromptu pool party invite to your boss’ place.
Yes, you should set your own style standards, but we’re here to help you enhance your current footwear lineup.
Let’s jump into it.
Must-Own Men’s Shoe Styles
1. The Low-Top Sneaker
Everyone needs a pair of kicks with a casual vibe that still uphold a clean sense of style.
Upscale high-tops pump the breaks, and bring you back to a simpler time—skate parks, no autotune on the radio, and the awkward ability to turn grunge clothes into a fashion statement.
Here are our top three picks for low-bearing kicks.
The mack daddy brand of low-tops. Leather and synthetic construction, rubber sole, breathable build on the toe box, and enough style to keep you looking dapper for days.
A slightly grayscale approach to the subject. Leather build, rubber sole, decorative lace tie-up, and a cushioned collar around your heel. Comfort that doesn’t kill your heels, at a price you’ll flip for.
Built for fashion, riding on solid construction. Fabric construction, two-dozen styles to choose from, textured outsole, and a synthetic insole. Fred Perry slips you into style for less than the average bear.
2. The Classic High-Top Sneaker
Let’s flip to the other side of the spectrum—high-tops. High-tops provide a lot of coverage without sucking your sole out through your wallet (see what I did there?)
Our favorite picks flaunt what you’ve got, and cover up the rest. These generally last a couple of years of constant use, and work well as Sunday outing beat-ups.
Jordans are like the cream of the crop, especially if you’re going for a clean, yet casual style. Leather and synthetic materials, a lace-up closure, and that same magnitude of Nike flair that we all know and love.
Ralphie’s got a lot to say here. 100% fabric, rubber insoles, and a plush padded collar, make these a comfortable, low-maintenance pair of sneakers that are proven to last.
Classic Converse, classic Chuck. You get all leather on the outside, a rubber sole on the inside, and a heel patch to keep those aches at bay. You can’t deny the signature look (we know you want it).
3. The Trainers
Every gent needs a solid pair of trainers to power through their day with.
And while they’re obviously essential for running or hitting the gym, you can rock the look casually, provided you’ve matched well with the rest of your outfit. Hey, you can even pull it off semi-formally if you’re Jerry Seinfeld.
Trainers allow you to be ready for anything. Need to chase down that cab or track down that escaping puppy? No sweat.
You’ve got to be one bold fellow to rock these, but we both know you can hold your own. Made of leather, the Flyknits come in a stylish box and fit like a glove.
If value for money is what you seek in your runners, then you’ve found your sole-mate with these bestsellers from ASICS. They boast mesh and brushstroke patterned underlays, GEL cushioning, and strong arch support. All at a decent price. What more do you need?
Simple mesh, TPU build, and a whole lot of breathability. Stave-off sweaty feet, and emerge looking like a champion. Merrel’s Vapor Gloves have a rubber insole, four styles to choose from, and unmistakable quality.
4. The Chukka Boot
It’s the hybrid model resting between a thick boot, and a slightly dressed-up look.
Despite their posh appearance, Chukkas are generally super durable. Think desert-campaign-style WWII-era boots.
Utilizing this shoe type properly will give you an approachable, yet masculine look.
Clarks throws an immense amount of stylish footwear options at you. And they’re all made of full grain leather, synthetic soles, and listed at a fair price. You want to go from dull to dapper in 3.2? This is how you do it.
These are bold borderline dress boots (which we’ll get into in a minute), crafted of full leather, sporting a synthetic sole, and a blind-eyelet lacing system for a smooth, suave look.
No shoe list would be complete without Timberland making an appearance. As you may have guessed, full leather construction here, but an added bonus in the Gripstick™ sole.
Further Reading: 11 Boots Like Timberlands: The Best Timberland Look Alikes
5. The Dress Boot
You’ve got a function to head to, but you don’t want to look like you walked out of the roaring twenties.
Dress boots add a little more height, keep you in comfort by wrapping your ankles, and often provide more insulation than standard dress shoes.
It’s like you can see a dress shoe being birthed out of a bangin’ boot. Red Wing isn’t chip, but it is all-leather, features a cork sole, and supplies homegrown jobs here in the US.
It’s a bit bold, but probably a hell of a lot more interesting than Johnny Suckup standing next to you at the corporate function. Man-made materials, a durable rubber sole, and a statement.
Wingtips are glorious, and Thursday Boot Co’s Lace-Up Presidents make a prominent statement about who you are and what you’re about. Leather build, rubber sole, they’re made from all the right stuff. But they also offer some of the best arch support going. This one snagged our editor’s choice.
6. The Oxford
Oxfords are characterized by their low heel and closed lacing system. And it’s the latter this that gives them that oh-so-peculiar yet classy look.
They come in multiple variations and they’re perfect for office wear, black tie (the less detailed versions), and smart-casual events. The Oxford should be your go-to whenever you need to look respectable.
And their versatility makes them a no-brainer inclusion on this list.
Clarks brings over 100 years of shoemaking flex to the table. With its modest style and focus on comfort, their Tilden Cap Oxford is perfectly suited to everyday business attire. They stay nice and dry and the cushioned insole will make you feel like you’re floating around the office. And who doesn’t like to float?
One of the best budget picks we found, La Milano brings a durable cow leather upper, cushioned footbed, and a rubber sole to its Captoe Oxford at a great price. It’s well reviewed and definitely worth a look.
This is the stuff stitch pattern dreams are made of. Everything about this eloquent oxford is magnificent, from the margin on the platform, right on down to the high-quality leather.
7. The Motorcycle Boot
Rugged and righteous, motorcycle boots give you that traditional masculine feel and appearance, while letting everyone else in the room know who’s boss.
Even if you’re not grabbing them for the ego trip, we’re sure you’ll enjoy the lineup we’ve assembled for you below.
Double buckles and supple leather give you a sleek, yet fierce look. Luxurious Italian leather graces your feet, while the platform adds some pep in your step, giving you a larger-than-life appearance (in a good way).
Ever wanted that weathered look without having to own the boots for years? The popular distressed appeal gives you a large heel, top-quality USA-made leather, and a pull loop feature along the cuff.
8. The Chelsea Boot
The Chelsea boot is the perfect representation of casual meets corporate. Falling somewhere between boots and dress shoes, they’re an awesome way to modernize your style.
Choose leather Chelsea boots for smart occasions, pointed for Friday Night drinks, and suede for casual (most popular and highly versatile).
206 Collective is a personal favorite of this writer: smooth leather, a glossed finish, and a healthy five-year minimum lifespan with proper care. These fit like a dream, add 0.5” to your heel, and have that trusty pull-on loop.
Slip in and out of any bar in style with this sexy suede pull-on Chelsea boot from Brooklyn’s own Steve Madden. It’s versatile, comfortable, and reviewers love it. A trifecta in our book.
Ted Baker never shies away from clean, proper style. This hits you with their price tags, but offers a killer quality of leather, solid platform, and elastane ankle support for a comfortable fit, every time.
9. The Penny Loafer
Penny loafers are the signature slip-on shoes of adulthood.
A step-up from the casual feel of our tenth item on the list, and a solid mix of high-end style, with that low-key desire to have a fun time.
Once the kingpin shoe of the 1950’s, and now, the newest addition to your walk-in.
Close your eyes and picture the most dapper version of yourself. Chances are, these bad boys are on your feet. And with good reason. Featuring rubber sole and Grand.os technology for optimal fit, we’re big fans of Cole Haan’s modern take on its OGP.
Solid rubber sole, top-quality leather, and all the comfort that you’ve been denied by your old dress shoes. Florsheim’s Jenson Penny’s are available in medium and wide widths and feature a cushioned leather heel pad—a huge plus as any invisible-sock wearer would know.
Rockport adorns a healthy section in most of our walk-ins, and for good reason. Their classic penny loafer is slim-fitting, has a decent arch, and features a foot-bed that conforms to your shape.
And if the penny loafer is a little too simple for you, you can always add a touch of flair with the classic horse bit loafer.
Idrese handmakes their shoes in Spain, and it's hard to find better quality than this. Made with a 360-degree Goodyear welt, these loafers shine with an Italian wide-lapel suit.
Based on Aldo Gucci’s famous design, horse bit loafers add a touch of sophistication and Italian gusto to an otherwise simple design.
10. The Boat Shoe
Last but not least, boat shoes made a serious comeback in 2017, and they’re no less popular this year.
Invented by Paul Sperry to help him stay sure-footed while out on his yacht, boat shoes have been a controversial fashion mainstay for over 80 years. And to weigh in on the debate—we like them.
They’re comfortable, casual, nautically functional, and above all else, stylish. if you want to stay on-point with your style in all situations, you’re primed for a set of boat shoes. Here are our picks.
It just so happens that sometimes, when you invent a category of footwear, you become the top dog of it. And that’s certainly the case with boat shoe pioneers, Sperry. The nautical bastions of style are renowned for their quality, comfort, durability and variety. You can’t go too wrong.
Colombia Sportswear Company are all about crafting no-nonsense apparel with a Pacific North western flavor. Incredibly light and comfortable, their PFG Bahama Boat Shoes are one of our favorite picks for everyday casual wear.
Margaritaville’s Anchor Lace’s are two parts rugged and three parts bold. That’s our kind of ratio. Constructed from leather and textile, they feature excellent stitching and a soft padded collar. They cover all the boat shoe basics and they’re easy on the wallet. Win / win.
What’d We Learn?
Wearing proper kicks to an occasion slip you into an ironclad sense of confidence. It paints you as a prophet of sensible male style.
If your walk-in doesn’t have at least half-a-dozen pairs of shoes on the rack, it’s probably time to slowly invest in building it out.
Your overall style and ability to be versatile with your wardrobe will dramatically increase with each style of shoes you introduce to your collection.
But the right shoes are just the start.
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Do you think we blanked out on a whole category of shoes? Let us know in the comments. And be sure to follow us on Pinterest to keep track of all of our ideas.