While there are plenty of footwear classics to pick from (like leather shoes and Chelsea boots), we’re living for loafers these days for their ability to dress up a T-shirt and jeans or give suiting a casual-cool vibe. While you’re probably familiar with the shoe term, you might not be familiar with the different types of loafers and the history behind them. Is it necessary to know? Maybe not, but if you’re going to spend your hard-earned bucks on a pair, it’s best to know a thing or two about what you put on your feet.

G.H. Bass was the first major brand to bring the shoe style to the American man back in the ‘30s with their classic Weejun loafers. The name of the shoe came from the slip-on moccasin-style that was noticeably worn by Norwegian fishermen (and basically is the style we call penny loafers today). Loafers (the name loafer refers to loafing in a field) became a hit by the ‘50s among the preppy set, and soon the tassel loafer was hitting it big, thanks to Alden Shoe Company and Brooks Brothers. Fun fact: “Tassel loafers” is also a term used to describe lawyers, because they loved to don them.

The popular luxe equestrian-inspired loafer that you’ve spotted everywhere these days (especially on Hollywood’s leading men) is the horsebit Gucci loafer that was created back in 1953. The loafer with hardware detail has been a status symbol of comfortable footwear for rich and powerful men over the years, and it’s worth the investment for timeless footwear, especially if you believe in cost-per-wear (and you can swing the price).

Thanks to different price points and styles that run from more classic to unexpectedly modern, you’ll wonder why these bad boys haven’t been a part of your life sooner.

1. Florsheim Men’s Pisa Moc Toe Tassel Loafer

This reasonably priced loafer comes with all the bells and whistles (and tassels!). Croc-embossed leather and a tassel take this loafer to stylish new heights with detail and texture to offset your sleek suiting. Known for their comfortable and stylish shoes at a price that won’t break the bank, Florsheim is always a sure bet to up your shoe game.

2. Steve Madden Men’s Novel Webbed Loafer

Not sure loafers are right for you? Steve Madden makes it easy to try out the style — without digging deep into your pockets — with their navy leather loafers with stripe webbed-detailing. Keep it casual and pair these loafers with your favorite T-shirt and jeans to wear on any Sunday funday for a snazzy look that’s totally comfortable.

3. Gucci 1953 Horsebit Leather Loafer for Men

Yes, you can still get the same iconic Gucci style that made a splash back in the ‘50s! While Gucci has put out newer versions of the horsebit loafer (some even with crazy cool embroideries), it’s a sure bet that this loafer (approaching its 60th anniversary!) is worth every penny to sport for years to come.

4. Want Les Essentiels Marcos Loafers

For a fresh look on the classic shoe style, Want Les Essentiels updated the penny loafer with a white and tan color-stacked outer sole to accent the smooth, black leather upper. Combined with a slimmer silhouette, this option is the perfect loafer for the modern man to incorporate into his everyday style.

5. Vince Comrade Lug Sole Penny Loafers

City Slickers with fashion-forward style will appreciate the timeless appeal of a penny loafer upper paired with a trendy, tough lug sole. Beyond the style appeal, the lug sole makes these penny loafers wearable for any crazy weather the new season might bring.

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