Penny and tassel loafers are among the most popular loafer styles in classic menswear. While they share the same slip-on construction, they each bring a different mood — one more relaxed, the other a touch more refined. That’s why I believe both deserve a place in a well-rounded wardrobe.
In this article, I’ll walk you through the key differences, explain when to wear each style, and share a few outfit ideas built around them.
Design & History
Even though they fall under the same loafer family, penny and tassel loafers come from different style traditions, and that shows in how they look and feel.
Penny Loafers
Penny loafers trace their roots to 1930s America. G.H. Bass introduced the style as the “Weejun”, inspired by traditional Norwegian slip-ons. The strap across the front — with a small slit that, legend has it, held a penny for emergencies — gave the shoe its nickname. With their clean, minimal design, penny loafers quickly became an Ivy League staple and a cornerstone of American preppy style.
They’re understated, unfussy, and adaptable, which is exactly why they’ve endured.
Tassel Loafers
Tassel loafers came onto the scene in the 1950s, born out of a custom request from actor Paul Lukas, who wanted a loafer with a bit more flair. Alden took on the commission, combining a sleek shape with decorative leather tassels, creating a new classic.
Tassel loafers quickly gained popularity among professionals looking for footwear that felt elegant but a touch unconventional. They have a slightly bolder, more dressed-up character than penny loafers, and pair especially well with tailored clothing — particularly when you want to make a subtle statement.
When to Wear Each
While both styles are versatile, they serve different purposes. The choice often comes down to the level of formality and the overall look you want to achieve. Below are the combinations I find work best for each.
Penny Loafers
Penny loafers are more casual, and I find them ideal for relaxed or smart-casual settings. They pair especially well with:
- Shorts, jeans, or chinos worn with a polo shirt.
- Jeans or chinos with a blazer.
- Jeans or chinos with a crewneck sweater.
- Unstructured casual suits, especially in linen.
They’re great for spring and summer outfits, casual weekends, or travel days when you want to stay comfortable without looking sloppy.
Tassel Loafers
Tassel loafers are a step up in formality and work best in more tailored or refined combinations. I usually wear them with:
- Worsted wool suits.
- Dress trousers with a blazer.
- Dress trousers with a merino wool rollneck.
- Suits with t-shirts.
They’re my go-to choice for business casual looks, dinners, or anytime I want something a bit bolder and more polished.
Choosing the Right Material
The material of a loafer can completely change how it feels and functions. I always think about how I’m going to wear the shoe before deciding between calf leather or suede.
Calf Leather
Calf leather gives loafers a more structured, polished look. I typically prefer it for tassel loafers, especially when wearing them with tailoring. A dark brown or burgundy calf loafer pairs well with flannel trousers, suits, or other dressed-up combinations. It’s also a practical choice year-round thanks to its durability.
Suede
Suede softens the shape of the shoe and gives it a more relaxed feel. It works particularly well for penny loafers in warmer months. I often wear suede loafers with shorts, chinos, or linen trousers — outfits where a glossy leather shoe might feel too formal.
Choosing the Right Color
Once you’ve decided on the material, color is the next thing to consider. It affects not only how versatile the shoe is, but also how formal or casual it appears.
Brown
Brown is the most versatile color for loafers, but the shade you choose makes a difference.
Darker browns are more formal and pair well with tailoring — they look right at home under dress trousers, suits, or a blazer.
Lighter browns, like tan or caramel, have a more casual feel and work best with medium to light-colored trousers — such as beige, light grey, or cream. They tend to stand out too much when worn with darker bottoms like navy or charcoal, which can throw off the balance of the outfit.
If you’re starting with just one pair, I’d recommend something in the mid-to-dark brown range for maximum versatility.
Burgundy
Burgundy adds some personality without being loud. I particularly like it on tassel loafers, where the color adds depth and complements navy and charcoal beautifully. It’s slightly dressier than brown but still quite versatile.
Black
Black is the most formal option and works best in tailored, structured outfits. I tend to reserve it for tassel loafers worn with a black or charcoal suit. It’s not something I wear casually, but when the occasion calls for it, it looks incredibly sharp.
Outfit Inspiration
To make everything above more concrete, I’ve put together a few outfits that show how I typically wear each loafer style. Each look is built around the combinations I mentioned earlier — so you can see exactly how penny and tassel loafers come to life in a full outfit.
How to style Penny Loafers
How to style Tassel Loafers
Penny and tassel loafers may belong to the same family, but they serve different roles in a well-rounded wardrobe. One leans relaxed, the other refined — and knowing when to wear each can make all the difference in how your outfit feels.
My advice? Don’t choose between them — get both. A pair of penny loafers will take care of your casual looks, while tassel loafers will step in when the dress code leans sharper. Build around your lifestyle, pay attention to materials and colors, and you’ll find yourself reaching for them more often than you expect.
