The Surprising History of Penny Loafers: From Preppy to Iconic

Today I am going to talk about how to style the penny shoes. For those of you hearing this term for the first time, it means the type of shoe that has a tongue at the top of the shoe that has just enough room to slip a penny inside. Usually this is a pair of slippers. It is easy to put together stylish and elegant-looking business-casual or semi-formal outfits. To better show you how to style it, I have compiled some of the best penny shoes outfit ideas that I have collected for you. Now let’s check out the cool list.

Black bomber jacket with penny shoes and mini shorts

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You are about to see a list of very unique and stylish outfit ideas. And to give you a little surprise to start the list, I’ll show you an artistic business casual outfit. As a top, you can wear a white loose-fitting blouse with a black bomber jacket. Pair them with green khaki mini shorts and a pair of penny shoes. Add a black felt hat for that cool artistic touch.

Black slim fit jeans with blazer and leather penny shoes

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To look somber and cool, simply wear an all black outfit. For a top, wear a black t-shirt with a black blazer jacket. Pair it with black slim fit ankle jeans. For shoes, wear a pair of black leather penny shoes. Add a brown leather clutch to complete the look with some color.

Blue puff shoulder blazer with cropped sweater and purple penny shoes

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This is an understated sexy outfit that is especially suitable for gatherings with friends. To create this look you can wear a white fitted slightly cropped sweater with a blue washed fitted puff sleeve blazer. Pair them with black leather skinny pants and a pair of purple suede penny shoes to complete the look.

White sweater with black knee length skirt and leather penny shoes

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The penny shoes or loafers are great substitutes for the black heels. The black heels can make you look elegant while the penny shoes usually make you look more stylish and artistic. For example, you can pair the black leather penny shoes with a white fluffy sweater and black knee length straight skirt to complete an attractive business casual look.

White lace blouse with black high-rise mini denim skirt

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To achieve this artistic and sleek outfit, wearing a high-rise skirt is key. In detail, wear a white lace short-sleeved blouse with a black high-waisted, figure-hugging mini denim skirt. Pair them with a pair of black leather penny loafers and a black fedora to complete the outfit in a stylish and artistic way.

White blouse with three-quarter sleeves and ripped black slim-fit jeans

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To look super breezy and minimal, this black and white look is for you. For the top, wear a white linen blouse with a relaxed fit and three-quarter sleeves. Pair it with black slim-fit jeans with a ripped ankle. Add a black and white leather handbag and a pair of black penny shoes to complete the outfit in style.

Long camel wool coat with black penny suede shoes

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To create this cool and grown up business casual look, you can wear a light camel long wool coat with a black sweater and black bodycon mini skirt to create some nice layers. Wear a pair of black suede penny shoes and a black leather handbag to add a feminine and dark touch to the outfit.

Gray button down shirt and light blue cuffed jeans

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In any case, some casual street outfits can be put together around the penny shoes. Here’s a good example. As a top, you can wear a gray shirt with a button placket and pockets in the front. Pair it with light blue cuffed slim fit jeans. Finally, round off your outfit stylishly and casually with a pair of black penny loafers.

Black blazer with leopard print blouse and penny loafers

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Here is a really nice demonstration of how to give your black outfit a grown up and elegant look. You should combine your black jacket with a blouse with a leopard print. For the rest of the outfit, you can wear black skinny jeans and a pair of black leather penny shoes.

Black leather jacket with white button down shirt and skinny jeans

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To look sleek and cool, adding some leather to the mix is ??a good idea. For example, you can wear a white button down shirt and a black leather biker jacket as a top. Team them with gray cuffed skinny jeans. You can wear a pair of black leather loafers with the shoes to complete the outfit in style.

White button down shirt and black pleated mini skirt

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To achieve this minimal and breezy look, you can wear a white oversized chiffon button down shirt and a gray pleated mini skirt as the focal point of the outfit. Pair them with a pair of black penny leather shoes. Finally, add some gold or silver bracelets to add a shiny and elegant touch.

Black sweater with ankle chinos and penny shoes

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To look cool and slightly unisex, you can wear a black fitted sweater over a white button down shirt and let the collar of the shirt peek out. Combine these pieces with black slim-fit jeans. Complement your outfit with black leather penny shoes for a stylish and artistic finish.

Light blue denim jacket with pink sweater and infinity scarf

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Now let’s look at a happy, girly and youthful outfit that will help you stand out from the crowd. As a top, wear a sky blue denim jacket with a pink sweater and a gray infinity scarf. Pair them with gray slim-fit trousers and a pair of black leather penny shoes to complete the outfit in a relaxed and stylish way.

Here are the penny shoes outfit ideas to make you look good and unique. Try it instead of constantly wearing heels to work.