Taking a Second Look: Penny Loafers

Heels may be a girl's second best friend, but we're all in tune enough to know that they're a nightmare for your legs in the long term. So I say we save them for a good night out and for day dressing we start exploring the variety of options for sleek flat shoes that can keep you fashionably on point. Penny loafers reigned for years in the 50s and 60s, and your mom will likely tell you that they were part of her every day wardrobe. The "penny" part comes from storing a shiny bright penny from your birth year in that central gap, which later became a dime. The dime was for one phone call home from a payphone. Every part of this story sounds alien, most notably because we really need to phase out the penny, but it's adorable all the same. 

Today's penny loafer is more likely to be worn with pants than a skirt, and we've completely left the mini sock look behind (thank God). The key is to treat your penny loafer like a ballet flat or a great pair of oxfords and make sure that the bony portion of your ankle is always visible. 

The first photo that inspired me to buy a pair!

I'd almost argue that loafers are a step up from ballet flats, only because the entire planet is now aware of the joys of the ballet flat. In terms of styling guidelines, wear with either a skinny jean  ending at the ankle or a loose/wide jean cuffed a few inches above to show off the shoe. The baggy sweater in both these outfits is a great touch with tons of texture and detail. Here, the loafers feels sleek and more adult than a beat up pair of Payless flats. 

You can also let loafers ground an ultra feminine dress. They look deliberate enough (when well cared for!) that they can stand on their own as a formality equal to the ballet flat. Here the loafer adds a bit of vintage flair to the green dress, and also links the plaid sweater to the modern printed skirt. 

There's something clean and classic about the loafers that translates well into a few different styles. Also, Alexa Chung is on board. And she gets into bed with Alexander Skarsgard, so she's basically on my hero list. Note that she's impossibly tall and long limbed, so she went with a more almond toed loafer that makes her seem even leaner. On some people the broad toe on a loafer can seem a bit clunky, so just keep an eye out for that!

You can also update the shoe leaving the traditional black and brown leather and going for a colored leather or a colored suede. You'll often see these advertised specifically as driving moccasins when in suede. The mint green, burgundy suede, and Anne Klein reptile purple feel incredibly modern.

Are penny loafers still too soda pop for your tastes or do you think you might snag a pair on eBay? I scored my Eastland reddish brown pair on eBay for about $10 and was thrilled with the quality. They're actually due for some care at the cobbler to be resoled, but the uppers are aging fantastically!