Have you seen our other popular Five Ways To Wear One articles?

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If you’re a regular Effortless Gent reader (or even if you’re just getting into all things menswear), there’s a good chance you’re in the process of getting your footwear and style basics covered.

Perhaps you’ve grabbed your trusty pair of dark denim and your reliable chukka boots. But there are certain footwear moves that can be a bit tricky to… step into? (Pun intended).

Maybe you’ve even ventured into pairing tailored shorts with some high-low style combos. One such style that may raise some eyebrows is the classic leather loafer; it’s up there with the double-monkstrap as a piece of footwear that some might forego in their rotation. But we’re here to show that:

  1. loafers are every bit as versatile as classic white sneakers, and
  2. they can be worn in ways that your father (or grandfather) never dreamed of.

It can be done! Come along with us and find out how.

It’s lucky that plenty of refined brands are doing the style in their own way, from classic footwear purveyors like Allen Edmonds to pricey and sleek pieces from J. Crew.

As you might expect though, we reach today for a premium piece at a solid price point – yes indeed, the pick featured below comes courtesy of the folks at Jack Erwin.

We’ll have more on those in a minute – ideal loafers if you want to try out the style. They can swerve more dressy thanks to the slim silhouette, yet they’re inherently a bit more casual. Why? Well… it’s a loafer, not a classic dress shoe.

You should select something much the same. While black loafers are certainly an option, the rich cognac color you see here (and a heck of a lot of other places) is more casual and ready for spring/summer.

Look for an upgraded loafer. While moccasin-inspired loafers do just fine, the construction and detailing leans more casual and laid back (tougher to dress up than the pair you see here). It’s all about balancing dressy and casual.

Well, that and taking care of the perfect pair of loafers. How to do that? Right this way, gents.

Fit and Care

Unlike most winter boots, loafers run fairly true to size (they also fit slimmer than thick boots). In lieu of being able to head into an actual store to try on your loafers (which is happening more and more these days), it is wise to follow a brand’s sizing guidelines.

In this instance, the Jack Erwin Archie Loafer runs true to size (according to the brand). You want a fit that’s comfortable and ready for wearing with no-show socks for the warmer months – as you’ll see, the looks below are geared in that direction.

Once they’re on (and off) your feet, care is going to keep them going for many spring and summer seasons to come.

The simplest step comes from some good ol’ shoe-shining. This will keep that leather rich and supple – perfect for wearing those bad boys in dressy situations. Brands like Kiwi offer inexpensive, easy-to-use shoe-shine kits that come with everything from brushes to shoe-shine towels.

Selecting the right shoe polish for cognac-colored loafers is tricky. Luckily, Kiwi (among other brands) has you covered there as well. Once you’ve got the right gear, it’s just a matter of shining them regularly to keep them up to snuff.

Added touches like cedar shoe trees help your loafers keep their shape while minimizing odor.

From personal experience, shining your shoes can be a nice part of a Sunday routine as you prep for the week ahead. Plus, those small steps in your routine make that quality last even longer.

So, that’s all sorted. Ready to step into some outfits? We’ll keep the style turned up and the puns turned down.

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#1. Crisp and Continental

At first glance, it might seem like this outfit has too much going on – loafers, plus a denim jacket? But bear with us…

If you’ve never given garment-dyed denim a look, spring and summer is the best time to do so. The color is a change of pace from dark denim and pairs nicely with a sturdy denim jacket.

A printed short-sleeve shirt in a slim fit is always a sure move for warm-weather style. Smart accessories like a heritage-quality belt and wallet complement the coganc loafers perfectly.

It’s an overall combo that might at first seem out of place. But, once you work loafers into ensembles that lean more casual, it gets easier and easier.

Five Ways to Wear One: Leather Loafers

#2. Sharp & Suited

Here we combine sharp tailoring with an equally sharp pair of loafers. It’s a step away from rocking sharp wingtips. This look will come off perfect at an outdoor wedding or a day at the office (don’t forget loafer socks, though).

For the spring and summer months, a classic navy suit serves you just as well as it would the rest of the year. Ditching the tie gives the whole ensemble a slightly more casual vibe, particularly with that crisp white shirt.

Stylish touches like an outstanding dress watch finish off this outfit quite well. Keep in mind that when you go with simple, tailored basics, it’s perfectly fine to rock a bit more of an eye-catching timepiece.

Five Ways to Wear One: Leather Loafers

#3. Easygoing Summer’s Day

Think stylish leather loafers can only be rocked with a suit or chinos and a blazer? Step outside the box and pick up a few upgrades over standard casual fare.

An upgraded casual T-shirt is a subtle way to switch things up from a slim pocket tee (although that would also work here). Tailored khaki shorts tie the look together with spring and summer vibes.

Clean sunglasses and a go-to casual watch are the finishing touches that make this outfit work. Add a sharp spring jacket if you need something extra.

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#4. High-Low Style

Combining navy shorts with leather loafers is nothing new – the supporting pieces take this casual ensemble up a notch. A baseball tee offers old-school athletic inspiration, while a navy quilted jacket adds a monochromatic factor and hybrid style (part field coat, part rain coat).

A clean, simple watch with a striped NATO strap splashes some color in an unexpected place. The classic Aviators are always a good sunglasses option.

Oh, and the loafers stand out just enough. It’s tough to beat white sneakers in this case, but loafers are a much more refined (and unique) option.

Five Ways to Wear One: Leather Loafers

#5. Travel-Ready

When you’re traveling between climates or seasons, sturdy, solid layers are your saving grace. Once again, these handsome Jack Erwin loafers complement a classic pair of dark denim perfectly.

Easygoing staples – a clean white Oxford and a washed indigo crewneck – are layering pieces that play off the dark denim perfectly. The grey linen jacket is simple and stylish; it’s also effective at keeping out chilly breezes as you move from place to place.

Mix things up with a webbed stripe belt and finish with a timepiece. This just might be the only watch you’ll need for a quick trip – it’s that versatile.

The Take Away

Don’t forget: one essential item – in this case, really well-built loafers – can help tie together an entire outfit.

That goes for casual ensembles as well as seasonally appropriate suits. And for those in-between situations, a crisp leather loafer can act as a casual middle ground just like a simple white leather sneaker.

Don’t be afraid to push the boundaries and mix some of the above pieces together – a baseball tee under a slim chambray suit, for instance. Or a graphic tee under a denim jacket. A good pair of loafers grounds each look (pun very much intended).

Loafers with an upgraded silhouette and rich leather tones deserve a place in your spring/summer footwear rotation. It will be a relief to finally slip into them after months of thick boots and chilly temperatures. Start with these outfits to create your own stylish ideas.

Tell Us: How would you style these loafers? Are you on-board, or are there any looks you’d add or switch up?

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PUBLISHED May 12, 2016


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.



  • Eugene Walter

    I can tell you from personal experience jacket + Florida + summer = no unless absolutely required as part of a formal outfit.

    • I hear ya. Omit the jacket, or in the case of a formal occasion, unlined + linen is your friend

  • Zac Silk

    I’ve got a pair of Bruno Maglis handed down to me by a family member. They’re a rich brown colour Funnily enough, I wore the exact same travel outfit going to Spain.

    It really worked well in the heat, and loafers are great with shorts.

    • Glad to hear you’ve successfully pulled off the look!