10 Chic, Transitional Penny Loafer Outfits for Fall/Winter Seasons

These penny loafer outfits are perfect to recreate for the fall/winter seasons! 

As the weather gets colder and the leaves start turning that reddish-orange color, it’s a sign to start wearing your fall/winter wardrobe. For many of us, we swap our sneakers and sandals for boots and shoes, and the one type of shoe I find myself always coming to during this time of year is my penny loafers. 

Sure, penny loafers are great to wear in the spring/summer, but there’s something about pairing penny loafers with your fall/winter wardrobe that will make any outfit look so chic. They’re the perfect shoe to have for this season because they really go with any outfit! 

If you’re looking for ways to style your penny loafers this fall/winter, here are 10 outfits to inspire you! 

10 Chic Transitional Penny Loafer Outfits 

1. Wool Cardigan + Wrap Mini Skirt 

This outfit is the perfect transitional look for fall/winter. There are brown tones, cozy layers, and, of course, penny loafers to complete! The patterns on the cardigan also add a bit of fun to the outfit since it’s such a stunning statement piece. If it’s a colder fall/winter day, keep the tights on, but if it’s a little warmer, you can always leave them at home!

2. Cropped Button-Up Shirt + Cardigan + Jorts

The bright colors in this outfit make it stand out, and I’m obsessed! It strikes the perfect balance of smart (with the button-up and cardigan) and casual (with the jorts), plus, the loafers themselves are both a smart and casual shoe!

3. Tee + Knit Vest + Maxi Skirt

This penny loafer outfit is definitely the most autumnal one so far in this list, pairing a T-shirt with a cozy cropped knit vest and a maxi skirt. The dark tones are perfect for the season, and the skirt is plaid, which is the go-to pattern for fall/winter. 

If you’re recreating this outfit on a colder day, you can always replace the tee with a long-sleeve shirt or thermal instead! 

4. Tee + Tie + Wrap Mini Skirt + Leather Coat 

If you’re looking for another smart casual look to style with your penny loafers, then this one is perfect! I love how the tie is used as a scarf; it gives the outfit a more polished look. The leather coat also makes the whole outfit look a bit more edgy while still being sophisticated! 

5. Top + Pleated Maxi Skirt 

This is the kind of outfit you can throw on with your penny loafers yet still look put together. All you’ll need is a plain vest top and a pleated maxi skirt. Then, add some more accessories, such as a necklace and crew socks, to make this look a little more interesting! 

6. Tee + Knit Vest + Leopard Print Pants

If you have statement pants in your fall/winter wardrobe, whether it’s leopard print like in this look, gingham, plaid, or any other pattern, they are perfect for styling with your penny loafers. Because your statement pants will be the attention grabber, you don’t want your outfit to be overwhelming with more patterns. So, pair your statement pants with a plain white tee and knit vest for a cohesive look! 

7. Oversized Button-Up Shirt + Knit Vest + Mini Skirt

We love an oversized outfit here, especially when it’s done so intentionally yet looks effortless! Wear a knit vest over your button-up shirt, and instead of tucking your shirt into your skirt, let the end be seen and become part of the look! Don’t forget to accessorize by wearing a necklace that will fit perfectly between the shirt’s collars!

8. Roll up Sweater + Mini Skirt + Trench Coat

For a cozier outfit, style your penny loafers with a roll up sweater and mini skirt. This is a great outfit to layer, as you can wear as many tees or long sleeves as necessary before putting on your sweater, and you can wear tights to keep your legs warm. Put on a trench coat to complete the look, and you’ll look so chic and badass!

9. Tee + Blue Jeans + Wool Coat

While this is a casual look, it’s the type of outfit that you really can’t go wrong with. Everyone has a pair of blue jeans in their closet, so it’ll be so easy to recreate, and it’ll be super comfy to wear. Style your penny loafers with blue jeans, a tee, and a wool coat for a cool girl look. Don’t forget to accessorize with a baseball cap too! 

10. White Long-Sleeved Blouse + Button-Down Dress 

What makes this a really chic penny loafer outfit is that while the outfit is monochrome, the penny loafers are snakeskin! Having patterned penny loafers immediately screams statement piece that must be worn during fall/winter, and they’re so gorgeously styled in this look!