What To Wear With Loafers: 18 Modern Looks For Men

For sartorialists, the loafer is about as commonplace and normal as shoes get, but if you grew up in Generation Sneakers, those pointy little slip-ons couldn’t be further from your wardrobe’s safe place.

And even if you don’t profess any allegiance to a particular shoe or generation, loafers should be on your style radar because they are one of the most versatile designs you can own. You can wear them with a suit or smart separates for a polished look or pair them with linen shorts and a polo while on vacation – there is a loafer for just about any casual look bar sportswear.

But as you’ll discover, loafers are challenging to pigeonhole since they come in various shapes and designs that suit different aesthetics. Below, we’ll show you how to pick the perfect look for your particular style.

Essential Advice For Loafer Lovers

Shape

Whether your loafer is a penny, tassel, Belgian or some other variant, its shape will largely determine how you can wear it.

Most loafers have a rounded toe rather than a pointed one, making them a comfortable slip-on style you can easily take on and off. The pointier the toe, the smarter the look. So, if you wear a lot of suits, you might want your loafer to have a more defined silhouette.

Contemporary ‘fashion’ loafers tend to be chunky, with oversized soles or grip details and accentuated elements such as tassels or metal hardware. They’re actually surprisingly versatile for an on-trend dresser since they’ll add a real edge to suiting but are also wild enough to be a statement in casual fits.

Material considerations

The material of the loafer is another critical component in determining how you style it. Almost all loafers are constructed from calfskin leather or suede upper, with the former being a smarter, dressier option than the latter.

Black leather styles spearhead the more sartorial bunch, whereas tan suede options are at the other end of the spectrum, but that’s not to say they can’t also be styled as part of a suit or smart separates. Patent leather styles have become popular with chunky contemporary loafers in recent years, too.

Silhouette

The third pillar of the loafer is style. There are four predominant sub-categories of loafers: the penny loafer, defined by the leather panel with a hole cut into it; the tassel loafer, so-called because of the two tassels attached to the upper; the horse-bit loafer, embellished with a metal bar or similar; and the Belgian loafer, which you could almost categorise as a slipper, such is its flexibility and softness.

Other variations have gained popularity in recent years, not least the backless loafer, which was given cult status when Gucci launched its fur-lined versions.

18 Cool Outfits To Wear With Loafers

Suede Loafers With Smart Separates

There’s smart, and then there’s elegant – this look firmly resides in the latter.

The off-white trousers and stunning blazer are tailored to perfection. While everything is top-notch sartorial kit, the sand suede penny loafers lend the look a softer and more relaxed finish than if you were to wear them with Oxfords.

Navy Loafers With White Pants and a Navy Cardigan

Taking a nautical approach is always a good idea when wearing white trousers, so adopting navy in this look is on the money.

The cardigan adds texture, the shirt adds pattern, the white trousers add contrast, and the navy suede loafers bookend the look with a casual tactility.

Brown Penny Loafers with White Pants and a Cream Shirt

A simple neutral-tone ensemble always looks expensive and well put together, no matter what. And so it goes with this outfit, which combines white and cream in a slim silhouette to create an understated, quiet luxury vibe.

The brown suede tassel loafers, meanwhile, add a punch of colour and texture to wrap it all up.

Brown Penny Loafers with White Pants and a Suede Jacket

Riffing on a 70s vibe, this look combines dark brown leather penny loafers with white tapered pants, a combination which could go in a number of directions.

With the green crew neck, it’s a modern preppy look that you could layer with a varsity jacket, but in this case, a vintage-style suede jacket has been used to stylish effect.

Suede Penny Loafers with White Jeans and a Black Polo

Monochrome looks are always a stylish option and difficult to get wrong, until you get to the shoes. This black polo shirt combines well with the white jeans, but the shoe choice is critical in rounding off the fit.

Black loafers would look too smart, and even brown leather loafers might jar a little, so the grey suede style chosen here is perfect, underscoring the outfit’s casual aesthetic.

Black Penny Loafers with an All-Black Look

The wearing of loafers is not restricted to long pants alone. As this all-black fit demonstrates, tailored shorts are also the perfect canvas for a smart pair of loafers.

Despite being essentially casual, the minimalist black look is inherently smart, if not contemporary fashion, and the addition of black loafers reinforces the elevated aesthetic.

Black Suede Loafers with Tapered Black Trousers and a Khaki Shacket

Suede loafers are inherently more casual than polished leather versions so they work really well when trying to dress down smart separates.

But equally, they can be used to dress up workwear garments such as this two-pocket olive shacket. Combined with the black tapered pants, they sign off on an easy-to-style everyday outfit.

Black Loafers with Black Pants and a Long-Sleeve Polo

The modern preppy aesthetic is one that has snowballed in recent seasons. The formula is essentially classic collegiate garments such as chinos, quarter-zips, and OCBDs matched with sportier pieces like long-sleeve polo shirts and rugby tops.

This look plays on that same idea, using the black polished loafers as a great way to keep the look polished without being ‘smart’.

Black Loafers with Navy Pants and an Olive Shacket

With a slim cut and straight leg, these navy pants are a great complement to a pair of black chunky loafers. They give the look a rugged appeal that a pair of sneakers could never achieve.

The addition of the workwear-inspired shacket adds to the sense of masculinity.

Brown Leather Loafers with Navy Pants and Cream Zip-Through

If you’re looking for a dressed-down Friday look as opposed to your Mon-Thur suit, then this outfit has all the right ingredients.

Rather than a blazer, this look uses a cream zip-through layered over a classic pale pink work shirt, alongside a pair of tapered navy chinos.

Office smarts, but with a hint of preppiness, it’s finished off with a pair of brown leather loafers.

Oxblood Tassel Loafers with Navy Pants and a Prince of Wales Check Blazer

While black and brown loafers are by far the most common styles, don’t overlook the power of a pair of Oxbloods.

With a rich, deep colour, born out best in polished calfskin, they bring an elevated feel to smart separates, as evidenced here with smart navy tailored trousers and a Prince of Wales check blazer.

Black Penny Loafers with a Tobacco Suit

The tobacco suit, especially when crafted in linen, is one of our favourite sartorial looks for a summer event.

The temptation is to pair it with a pair of similarly toned suede or leather loafers, but in fact, black leather loafers make the suit pop more, as evidenced by the fit above.

Sand Suede Loafers with Grey Chino Shorts

Shorts don’t necessarily have to be the tailored variety to work with loafers, but it certainly makes things easier if they are. These smart chino versions have been nicely paired with some sand suede loafers and worn notably sockless for a clean, off-duty look.

The fitted grandad collar shirt and nonchalantly slung cream sweater channel a classic East Coast preppiness that’s perfect for summer.

Chocolate Brown Loafers with Tailored Grey Shorts and a Linen Shirt

This ensemble is a casual yet elevated look for the summer and a slick example of combining interesting textures to create a bold look, even while using an understated colour palette.

The loafers verge on espadrilles, which is a nice touch, underlining the casual credentials of the fit.

Chunky Loafers with Straight-Leg Cropped Jeans

As simple and laid back as it gets, the easy combo of stonewashed jeans and a white T-shirt is as timeless as any pairing your wardrobe could muster.

While most people would reach for a pair of sneakers here, the brown leather loafers add a much more creative and stylish edge.

Suede Loafers with Jeans and a White Cuban Collar

Similar to the look above, this outfit revolves around the easy pairing of white and blue, only this time, the tee is swapped for a slightly dressier white Cuban-collar shirt.

The same brown leather loafers would work fine, but instead, a grey suede tone is used, which has less of a colour contrast and makes the look softer and more understated overall.

Dark Loafers with Selvedge Denim Jeans

Every wardrobe should have at least one pair of selvedge denim jeans. Typically cut from raw Japanese denim, these rich indigo-dyed styles can be easily dressed up or down.

Loafers, as shown here, offer the perfect way of dressing them up, while the shawl-collar cardigan adds a good dose of neutral colour and texture.

Black Penny Loafers with Straight-Leg Stonewashed Jeans

This is another great example of a simple off-duty summer look that would usually worn with sneakers. Yet adding the black leather loafers brings a different edge entirely.

The stonewashed jeans are really casual, so by bookending the look with a sliver of smartness, you elevate the outfit.