The 4 Best Loafers For Men In 2020 [And How To Style Them]

Loafers are making a big comeback in men’s fashion this season. And I’m not just talking about your dad’s favorite penny loafers or those Sperry boat shoes (eww) that people love to pair with pastel 5-inch shorts. I am talking about loafers than can be worn to work (whenever we can safely go back) with a pair of nice slacks all the way down to loafers that look great worn sockless with a pair of Patagonia baggies.

Why have loafers made a huge comeback? It’s a combination of reasons. 

First off, slip-on shoes like those from Vans are more popular than ever for both men and women. Second, casual styles have matured in the past few seasons resulting in a more dressed up look - even when you’re dressing down on the weekends.

The result: a resurgence of the classic slip-on dress shoe: the humble loafer.

Loafers are the perfect summer shoe for men. They are easy to slip on and off, they are dressed up enough for business casual, and they are relaxed enough to wear to a pool party.

As the hosts of fashion podcast Throwing Fits would say, we’re living in a post-sneaker world. It’s time to catch up. To help up your summer loafer game, here are the 4 best loafers for men in 2020.

The Entry-Level Option: Rockport Men's Classic Penny Loafer

If you are just getting starting with loafers and want something extremely versatile, check out the Rockport Men's Classic Penny Loafer. These loafers don’t have tassels or horse bits or anything like that, and that is what makes them great. They will dress up a pair of jeans and they’ll go great with a pair of pressed Chinos.

The Throwback: Dockers Men's Sinclair Kiltie Loafer

I mentioned your classic “dad” style loafer earlier and here it is again. The Dockers Men's Sinclair Kiltie Loafer features tassels and moc-toe stitching for a retro look perfect for more casual office environments or weekends with the boys.

The Classics: Bass Weejuns

The Weejuns from G.H. Bass and Co. are an American classic. The brand has been around since 1876 and has been churning about high-quality leather footwear ever since. They offer a wide variety of loafer styles (which they call Weejuns) and you can’t really go wrong with any of them.

If you’re just getting your first pair of loafers and want to play it safe, I recommend classic Larson. If you want to class it up a little bit, go with the Lincoln.

My current favorites are the Palm Springs Larkin Weejuns because I am a sucker for a good tassel and the low profile sole makes them a little more casual compared to the traditional style.

The High-Fashion Icon: Gucci Men's Leather Horsebit Loafers

When it comes to designer loafers, no one beats Gucci (although Virgil Abloh at Off-White is giving Gucci a run for their money). The Gucci Horsebit Loafer is often imitated (see the Bass Lincoln, for example), but if you have the money to spend and you want to flaunt it, you can’t beat Gucci.

What to Wear With Men’s Loafers

I mentioned in the introduction that loafers are extremely versatile. Depending on the style, you can wear them pretty much anywhere. Here are a fit outfit inspiration ideas to get you started.

Casual

For a casual look, grab a pair of tan loafers with a subtle sole like the Palm Springs Larkin Weejuns and pair them with a pair of khaki shorts or cropped pants. If you’re going for this look, skip the socks (or grab a nice pair of no show socks, these are my personal favorites).

Business Casual

For a more business casual look, opt for a pair of nice slacks and a casual pair of loafers in pretty much any color. If you want to show off a bit, grab something in burgundy or wine colors. In the summer, feel free to go with no-show socks. If it’s cold out, don’t be the guy showing off your ankles with snow on the ground.

Dressed Up

You can dress up loafers to an extent, but if it is a fancy black-tie event, leave them at home (Gucci may be an exception here). You can certainly wear a nice pair of black loafers with a suit in the summer - always with socks. Suits with no socks is a corny look that you’re going to regret when you look back at old photos.‍

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