What To Wear With Classic Loafers

What to Wear with Classic Loafers

The loafer is a dressy type of closed-toe shoe, coming in many different styles. I personally prefer the classic horsebit loafer, but the traditional penny loafer is another cool option! In the 1930s, when phone booths were still the norm, the loafer was designed to comfortably slot in a single penny that the wearer might use on a phone call. And while pay phones have since given way to modern landlines, smartphones, and other innovative devices, the penny loafer has never gone out of style. The shoes are typically associated with professionalism and finesse, and as such, they’re a fixture of preppy fashion styles for both men and women. Whereas the horsebit loafer was made popular by Aldo Gucci and invented in 1953, inspired by the traditional moccasins.

Both loafer designs are extremely popular and are still standing the test of time! Don’t let the penny loafer’s polished reputation scare you too much though. Even for those who aren’t used to wearing them, these shoes are pretty easy to style. They also have the effect of elevating even the simplest outfits and making them appear more urbane and refined. Below are some outfit ideas that, when paired with penny loafers or horsebit loafers, are guaranteed to make you look like a million pounds:

The No-Fail Button-Down and Tailored Bottoms Combo

One virtually failproof combination that you can always finish off with a pair of loafers is the button-down shirt and tailored bottoms ensemble. Well-fitting shirts and bottoms will streamline your figure and make you look effortlessly put together—a fact that can be emphasized with some handsome leather loafers and matching accessories.

To turn an ordinary day at the office a little more extraordinary in terms of your personal style, pair a crisp button-down shirt and a pair of Ponte pants or leggings with plain black or two-toned loafers. Finish the ensemble with a matching leather belt and watch for a look that will exude respectability and self confidence.

The Preppy Sweater and Skirt Combo

Your collegiate days may be over, but there’s never a bad time to rock the academic-chic aesthetic. You’ll be able to achieve this perfectly with a woolen or knitted sweater vest over a polo shirt or boyfriend shirt, a pleated skirt, and some opaque women’s tights with caramel, chocolate brown, or oxblood loafers.

Pair your outfit with some distinguished accoutrements, like a leather satchel and some statement eyeglasses or sunglasses, and you’ll be ready to take your fashion followers to school.

The Artsy T-Shirt and Distressed or Patterned Bottoms Combo

Penny loafers aren’t only for the bookish or preppy crowd. If your style relies more on casual clothing staples like T-shirts and jeans, there’s a way to combine them with loafers that will strike a perfect aesthetic balance between sophistication and a rebellious and spirited edge.

Try wearing penny loafers in an unorthodox colour—like mustard yellow, navy blue, or emerald green—with your favorite oversized tee and some distressed shorts or a pair of plaid pants. You’ll be surprised at how well you can still capture the zeitgeist of your generation with shoes that are considered more “vintage” in their design.

The Chic Monochromatic Combo

Want to try wearing a pair of loafers that sport an unusual colour combination or accent, for example snakeskin or leopard print? The best strategy for pulling off a statement pair of penny loafers is to wear a simple monochromatic outfit and let the shoes do the talking.

Put on a playsuit or mini dress, or combine a top and a pair of bottoms in different shades of the same
colour. Use your monochromatic outfit as a blank canvas that will allow a pair of statement penny loafers to shine in the spotlight. However, if bold loafers aren’t for you, opt for a white pair with your monochrome outfit, and it’s a very chic ensemble!

The Summery Polo Shirt and Shorts Combo

It’s easy to associate penny loafers with indoor looks that utilize lots of layers, and that probably makes
them an intuitive option for you in the cooler and windier months. But they’ll still look good on you
when summer comes, and you should consider wearing them with smart-looking polo shirts and shorts.
This airy, but dignified combo will be great for outdoor events and photo ops during your travels out of
the country.

The Loafers and Denim Jacket Combo

Lastly, for an adaptable combo that would look good on a variety of occasions—from a casual night out
with your friends to a date with your special someone—bring out your favourite dress, a reliable denim
jacket, and a pair of loafers in a delicate colour like beige or rose pink. Your shoes will surely add a
touch of poise to your ensemble and make your venture outside a more enjoyable one. If a dress isn’t your thing, wear a pair of jeans with a denim jacket and it works just as well!

As you can see from the combinations above, there are a lot of great outfit options for a familiar, but
timelessly elegant shoe type like the penny or horsebit loafer. Don’t hesitate to pair your loafers with either preppy ensembles or casual combos that you would otherwise finish with boots or sneakers.

Which outfit idea appeals the most to your personal style, and on what occasion will you sport a trendy pair of loafers? You can check out more loafer outfit inspiration below.



  1. May 29, 2023 / 4:14 pm

    I love all of your outfits, Lorna, the photo of you on the fence is beautiful. ❤️☺️🇬🇧

    • Lorna
      May 30, 2023 / 2:30 pm

      Thank you so much, John! I really appreciate that!

  2. Mica Away From Blue
    May 29, 2023 / 10:47 pm

    You wear all your loafers so well! I think they perfectly suit your classic style 🙂

    • Lorna
      May 30, 2023 / 2:30 pm

      Thank you so much, Mica 🙂

    • Lorna
      June 1, 2023 / 2:32 pm

      I totally agree!

  3. Frogger
    June 3, 2023 / 3:46 pm

    So cute and beautiful outfits 🙂

    • Lorna
      June 5, 2023 / 4:32 pm

      Thank you 🙂

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