The following is a guest article from Beau Hayhoe of The Style Guide.

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Quick, look at your feet right now. What are you wearing? Dress shoes? Boots? Bunny slippers? Or maybe, just maybe a great pair of sneakers?

If so, you’re in luck. Because today is all about great sneakers.

When it comes to footwear, some are way into sturdy boots, some swear by crisp dress shoes, and others are what you might call sneakerheads. Whatever your preference, you don’t need a closet full of styles to appreciate (or wear) a great sneaker.

In the right situations, a well-crafted sneaker can get just as much wear as a thick pair of wingtip boots or captoe Oxfords.

For proof of versatility, look no further than the fact that high-end designers are now evangelizing the sneaker as a premium piece of footwear in the modern man’s wardrobe.

As with any premium wardrobe item, price is a concern (especially with the inflated costs associated with “rare” or “deadstock” sneakers) but thanks to direct-to-consumer retailers like GREATS, sneakers no longer have to be cost-prohibitive.

If you live around Brooklyn, perhaps you’ve had the chance to visit the new GREATS storefront – but more than likely, this is a company you’ve come across on the Internet or even right here on Effortless Gent.

Over the last two plus years, GREATS has certainly exploded in the digital menswear scene for their mix of affordability, quality and variety. And seeing as the company both sources leather from and constructs many of its shoes in Italy, a hotbed of premium shoe construction, they’re a brand you can trust for quality.  

Today, we’ll discuss how to rock three modern variations on classic sneakers from a great (ahem) company that’s quickly stepping into classic status.

The Low-Profile Runner

Stay Clean With These Three Classic Sneaker Styles

Outfit #1

Stay Clean With These Three Classic Sneaker Styles

Outfit #2

At first glance, the Pronto might seem like an odd pick for a versatile shoe. It certainly isn’t the silhouette most of us think of when picturing a classic sneaker (that would be the Wilson, more on that later).

But it’s a surprisingly sleek shoe crafted with a premium rubber outsole and finished with ballistic mesh, providing that elusive mix of sturdiness and comfort. The bison leather and rich color only add to the premium feel, which should nicely complement higher-end accessories like the Shinola leather watch.

However, it’s available in a plethora of colors, so if the above option isn’t your speed, there are other colorways to choose from.

Adding to the versatility, that premium leather means they’re an excellent “high-low” shoe — sleek enough to be worn in place of dress shoes for a business casual occasion and sporty enough for casual layers.

The Classic Captoe

Stay Clean With These Three Classic Sneaker Styles

Outfit #1

Stay Clean With These Three Classic Sneaker Styles

Outfit #2

While the Pronto is the 21st century’s answer to a new classic sneaker, The Wilson plays off a rather iconic silhouette in a way that’s unique to GREATS. The price point ($50) is also a big help.

Because the captoe sneaker is such a well-recognized silhouette, that means you can mix and match at will — more eyecatching pieces like black denim and a heavy shawl cardigan are grounded by the pared-down look of the sneakers, which are simple enough to support most styles.

Like a blazer paired with a chambray shirt, for example. As long as they both fit slim, you’re all good in a captoe like The Wilson. Think of them any time you would wear leather chukka boots.

The Luxury Hybrid Boot

Stay Clean With These Three Classic Sneaker Styles

Outfit #1

Stay Clean With These Three Classic Sneaker Styles

Outfit #2

For those looking to pack an even bigger visual punch with their sneakers, the Hirsh is a strong contender. It draws on the classic design of the functional desert boot, yet the EVA-equipped outsole blurs traditional footwear lines in a compelling way.

Try a basic tan suede color and they’ll wear just like a plain ol’ tan suede desert boot, albeit with a little extra style. Staples like slim grey denim or navy cords will help accentuate the sneaker and give you some room to play with the top half of your outfit.

Mashing together a crisp navy blazer, a chambray shirt and a knit tie is one way to go, but that same chunky shawl cardigan can pull double-duty in a casual, comfortable off-duty outfit. And if you’re going to try out a hybrid style, it’s tough to beat a well-crafted option for under $150.

When first looking into purchasing a new, more daring pair of sneakers, the same menswear rules still apply, which is comforting for us Lean Wardrobe guys. Look for styles in neutral colors (think grey, tan, navy or olive) and build the rest of your outfit as you might around a more traditional sneaker.

Once you do that, you can craft outfits that might normally feature something like a wingtip dress shoe or boot. Using this approach will lead to new, unexpected outfit combinations that will work for the office and off-duty hours. This will help you make the most of your new (or new-ish) kicks while adhering to a Lean Wardrobe philosophy.

Eventually, you might find yourself making new style rules for your closet. And that, my sneaker-loving friends, is what versatile style is all about.

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Your turn

Do you have these sneaker styles in your wardrobe? What’s your favorite sneaker to wear on your casual days? Let us know below!

If you found this article useful, make sure to check out our Lean Wardrobe resources page.

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PUBLISHED December 8, 2015


A Michigan State University alumnus, Beau works in the fashion division at New York City's Coyne PR. In addition to writing for Effortless Gent, Beau's menswear writing has appeared on Dappered, VOUCH Mag, and GearHungry. He also runs his own blog, The Style Guide.



  • Andy Budnik

    Whoa, I missed this one. I’ve never heard of Greats, but these three shoes are pretty sweet. I think I prefer the Rosens in khaki though to the Pronto. Definitely will be looking at these in spring – fall and winter are my boot seasons.

  • Vernon

    Jack parcels enough said the classic