How To Wear Loafers – Show Your Ankles

personal stylist

personal stylist

Loafers are for ankles. And when I say loafers, I am referring to those rounded toe, slipper like, moccasin shaped shoe. Not pointy or square toe dress loafers.

What Should I Wear With Loafers?

Ideally, loafers should be paired with crisp shorts. They also look sharp with rolled up jeans and chinos. If you are feeling extra spicy, a cropped summer suit will work as well. Why? Because loafers are for ankles. Naked ankles to be more specific. If you can, don’t wear socks with your loafers. If you need socks for hygienic or comfort purposes use no-show socks, preferably no-show socks that are the same color as your loafer in case they want to peak out and see what’s up in the world.

loafers with shorts

Jack O’Neill Shorts

What Can’t I Wear With Loafers?

Basically, you shouldn’t be wearing loafers with slacks, jeans, chinos or suits, unless of course those slacks, jeans, chinos and suits have cropped or rolled pant legs. The reason you don’t wear rounded toe loafers with longer pants is because it makes your legs look short and your feet look stumpy. When you display skin and leg with the round toe loafer, the stumpy effect stops short (pun!). In other words, exposing the curves of your calves and/or ankles creates a defined and lengthening line for your lower half.

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Photo Credit: Caroline McCredie

What Loafer Do You recommend This Summer?

I love a grey shoe in general, but a grey loafer is the dog’s bark. Cole Haan has made a cool canvas penny loafer in a nice slate grey color. You can pair these with navy shorts, rolled blue jeans, black shorts, and swim shorts as well. Although if you are looking for a water friendly loafer, SWIMS has an awesome waterproof grey loafer. For a grey loafer to pair with a sharper rolled up jean or rolled up white chino, Carlo Pazolini has made a handsome nubuck penny loafer. Note: Grey loafers need grey no-show socks.


how to wear loafers

Cole Haan $77.95


how to wear loafers

Swims $159

suede grey loafers

Carlo Pazolini $185

1 Comment

  • Antonymous says:

    Hi, nice article, indeed I alternate no socks and ankle socks in shorts with moccasins, the style it depends, from neutral dark colors blues, and greys to more colorful, non flashy emeralds, turk blue or, sometimes stripes, and I agree with you they are great with bare ankles too!
    Although being them so flexible I find they work even in normal jeans, or even i suits, still with socks, in this case.

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