The Cult Of Loafers And How To Wear Them

I have worn my pair of penny tassel loafers to death after I bought them in November last year for my brother’s wedding. You can call me a disciple of the loafer movement that seems to get even the most loyal streetwear enthusiast to rock these shoes that seemingly works with any outfit you wear it with. Well, almost any outfit.

My Sebago Dan Penny Loafers of the tassel variant have seen many roads and parts of my life at this point in the six months I’ve had them. These were my first pair of honest-to-goodness leather penny loafers after pining after them for years.

I finally bit the bullet after using my older brother’s wedding as an excuse to snag a pair and to write it off as a familial expense. Most of my life I’ve been a sneaker guy and really only saw loafers as something my dad or my uncles would wear so their feet wouldn’t hurt while driving.

Everything changed for me when I saw Tyler the Creator, a musician I adore tremendously, unapologetically rock classic tassel loafers with white socks and cropped pants. The worlds of Hip-Hop and classic men’s fashion colliding made the gears turn in the limited menswear section of my brain.

It was so jarring to me but also a critical point in expanding my wardrobe beyond Nike Dunks and parachute pants.

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I decided it was time for me to start advocating for this article of clothing that has assimilated into my personality as someone trying to be fashionable without much effort.

There is also something mesmerizing about living a life out of these shoes or when they look worn compared to how loafers look fresh out of the box. You might even prefer how cool they look and how much character the shoes get when they get really beat up.

Wearing these shoes almost always feels like you are out on important business or meeting high powered executives, even if you’re just actually out to buy groceries.

If you drop a substantial sum of money on a bespoke, quality pair of loafers, these could even be heirlooms much like vintage mechanical watches.

Lug or Leather? Why You Might Need Both

The lug soled loafer has been soaring in popularity recently due to its more casual-yet classy look that many streetwear discerning individuals have found easier to transition to rather than something like wing-tip shoes.

We might have to thank the Doc Martens Adrian Tassel Loafers for this after it seemed to be on every men’s fashion Pinterest inspiration board.

These shoes have become ridiculously popular in the last few years as people try to look classier while keeping a chunkier alternative silhouette.

You may not have known that penny loafers were originally made to easily store two cents in case you needed to make a call on a payphone back in the old days, or at least that’s how the urban legend goes. They also have a distinguishing “beef roll” or the leather build up on the sides of the iconic leather strap with the slot in the middle.

Lug or foam sole loafers, which have raised textured rubber “lugs” intended for traction, bring a more contemporary and casual look. In comparison, leather outsole loafers feel heavier, more premium, but take a bit of time to break into.

Loafers outfitted with these foam souls presents a more outdoorsy comfort and security if you happen to be wearing these shoes on unfavorable terrain.

The Sock Question

Now it's time to pick out what socks to wear with these shoes or to just brave the storm and go sockless as you set off with your new loafers.

A fashion rule you might have heard of is to match your socks with your pants but this isn’t really a hard and fast commandment to swear by. It's really up to you whether you want your socks to match or not as long as you have the confidence to pull it off.

White socks and black loafers is a look that has had a style resurgence, whether to pair this combination with jeans or dress pants to give a high class look with purpose. The rather simple but contrasting style choice is a callback to the 1950s and 1960s casual menswear, which was popular with Ivy League students in the United States. So don’t be afraid to switch to white socks; people won’t think you’re Michael Jackson.

That said, here're some of our picks of loafers you can’t go wrong with:

1| G.H Bass Weejuns

The two-toned black and white Weejun Loafers from G.H Bass are probably the most stylish pair of loafers you can get at a price that's not astronomically expensive. These are probably the quintessential pair of penny loafers that menswear connoisseurs preach as must-haves. In the Philippines, the Weejun Loafers usually go for P11,000 brand new or about P4,000 pre-owned.

The legendary loafers, which was introduced in 1939, is a footwear staple that has been worn by cultural icons such as James Dean and the late US President John F. Kennedy. And now more than ever, these shoes remain the benchmark for timeless shoes you can’t go wrong with.

2| Sebago Dan Loafers

Another pair of classic loafers, the Dan Loafers from Sebago also have different iterations such as lug sole or tassel style pairs. A cheaper alternative to the Weejuns that capture the same look and go for about P9,500 brand new and can be picked up on-sale for about P6,650. You can’t beat the quality hand-sewn and classic finish these bring for half the price of Bass’ slip-ons.

3| Marquina

A brand from the shoe capital of the Philippines, Marquina traces its roots in 1956 Marikina and the penny loafers they offer mean business. Their handmade, full-grain leather Grand Penny Loafers in Black Noir are priced at P7,690 on their website and local boutique shops. These made to order locally made slip-ons are made to last with a stacked leather sole outfitted with memory foam footbeds.