For The Love Of Loafers

Loafers are a great go-to shoe for nearly every season, but the trick is knowing when and where to slip on a pair without looking like a rookie.  But don’t worry, we’ve put together a can’t-fail loafer guide that will show you the ropes and have you pulling off the perfect loafer style from season to season just like a veteran.

While there are different varieties of loafers, most slip-on, dress shoes can roughly be classified as loafers, and this style of shoe has shaped much of the menswear landscape for the better part of a century.  For the everyman’s purposes though, there are 4 primary varieties of loafers, each with a different style and vibe, not to mention level of formality.   So, before you even think about slipping into a pair of your own, it makes sense to brush up on the ins and outs of each style, and what to wear ‘em with.

Penny Loafers
A classic, casual option that has been an essential staple since the late 1920s, the penny loafer is known for the small pouch found in the front of the shoe. Some used this space to store coins in the slit as a style statement, while others say the slit was designed to hold enough change to make an emergency phone call.  Regardless of what you use it for, penny loafers have evolved from their preppy beginnings into the utmost in versatility when it comes to casual dressing.

Wear Them With: Perfect with your favorite pair of chinos, slim-fit jeans, and nearly any casual trouser or suit pants.  Dressing them up formally can be more dicey territory though, so use caution.  If you’re going for a more casual vibe with a suit (lose the tie) they can work, but outside of that, it’s best to keep the penny loafer to more casual situations.

Driving Loafers
The tell-tale rubber, high-traction soles on the bottom of modern driving shoes is what makes these slip-ons unique. Designed without a heel, as not to get caught on a driving pedal, driving loafers were originally designed just for that: driving, and are typically made of supple leather or soft suede, so they’re easy to slip on and off.  Lately, designers have made all-purpose versions of the driving shoe that allow men to wear them in non-driving conditions, too.  Today’s modern driving loafer is the ultimate in laid-back style and a great casual shoe.  

Wear Them With:  Anything casual, from denim and chinos to shorts.  Even more casual than a penny loafer, these loafers are strictly for relaxed dressing, so skip the suit.  Also, be prepared to show a little ankle, as these are generally worn without socks.

Horse Bit and Tassel Loafers
These embellished slip-ons are beacons of vintage style.  Horse bit loafers (named for the metal “H” on the top of the shoe that resembles, you guessed it, a horse bit), made wildly popular in the 1960’s and 70s by Gucci, were a crowd favorite among the business elite and Wall Street up-and-comers until the late 1980s. Nowadays, they’re still synonymous with the Italian fashion house that first created them, but are widely worn by all walks of life.  Tassel loafers, on the other hand, have a history of being a tough, versatile shoe known for its timelessness.  A longtime preppy favorite, the tassel loafer enjoyed a recent surge in popularity as dandy styles returned to popularity.  Similar in look and style to boat shoes, they’re a more formal variation that’s easily recognizable by the leather tassel-like straps found on the front end of the shoe.

Wear Them With: Like their closest cousin, the penny loafer, both horse bit and tassel loafers are a dressy casual staple.  Wear ‘em with denim and chinos if you want to dress up your casual looks with a bit of extra style.  As with penny loafers you can wear them more formally but unless you’re dressing down your suit slightly, they’re best left for more casual vibes.

Dress Slippers
While your favorite pair of flannel-lined slippers is definitely your go-to move for an afternoon of Sunday football, we can’t really recommend rocking those with your favorite pinstripe suit to that Wednesday morning meeting.  What we’re talking about here is a true “dress slipper”, a shoe that’s sort of a hybrid; part dress shoe, part low-profile slip on.  They’re most commonly found as a stand in for a more traditional lace-up patent leather tuxedo shoe but have evolved to include dandy-inspired versions in velvet and leather that can be worn with suits or casually. 

Wear Them With: A patent or black leather slipper is a cool way to mix up your formal footwear and add a retro vibe to your black-tie ensemble.  Just be sure to shorten up your hem slightly and wear with confidence, just like The Rat Pack did.