We’ve all been there…
You’re browsing online, fall in love with something, buy it impulsively, and then when it arrives you’re left scratching your head wondering how to actually wear it. For me, this happens most often with footwear—and that’s exactly what happened when I received these gorgeous Myrqvist Stenhammar II penny loafers in black.
Black loafers seemed straightforward enough to style, but they didn’t click for me right away. After some experimentation and practice, I’ve put together five different outfits that showcase just how versatile these shoes can be. Here’s what I learned about styling black penny loafers.
The Key to Success: The Sandwich Method
Before diving into the looks, let me share the styling trick that made everything click. It’s called “the sandwich method”—a technique where your top and shoes are the same or similar color (the bread), with a contrasting color in between (the filling). This creates visual balance and was the key to making these black loafers work across multiple outfits.
Elevated Casual
Starting with an elevated casual look that’s perfect for spring and summer, I built this outfit around a simple yet sophisticated color palette. The foundation is a navy lightweight cotton twill chore coat layered over a heather gray t-shirt, creating that effortless layered look that works so well in transitional weather. The navy and gray combination is timeless and versatile, serving as the perfect backdrop for the rest of the outfit.
For the bottom, I chose white cotton trousers and deliberately skipped the belt despite the belt loops. This keeps the look cleaner and more casual, preventing it from feeling too structured or formal. The white trousers brighten the entire ensemble and create a fresh, summery vibe that works beautifully with the darker tones up top.
The black penny loafers are the perfect finishing touch here, grounding the lighter elements while adding a touch of sophistication. Paired with no-show socks, they maintain the casual, breezy feel that’s essential for warm weather styling. The overall effect is polished but relaxed, making this outfit ideal for everything from weekend brunches to casual Friday at the office.
Old Money Modern
This outfit perfectly captures those coveted old money vibes while incorporating a modern high-contrast approach that feels fresh and contemporary. The foundation is a black cotton pique button-up shirt that provides structure and sophistication, serving as the anchor for the entire look. The texture of the pique fabric adds visual interest and prevents the black from looking too flat or monotonous.
The real star of this outfit is the cream cable knit cashmere sweater worn draped over the shoulders. I’ll be honest—this styling choice intimidated me at first, but it’s all about building confidence through practice and repetition. The cable knit pattern adds texture and visual depth, while the cream color creates a striking contrast against the black shirt. This combination of colors and textures is what gives the look its modern edge while maintaining those classic preppy undertones.
Stone cotton trousers complete the ensemble, bridging the gap between the high contrast of the top half. The addition of a black leather belt creates continuity with the shirt and shoes, while the stone color keeps the overall palette sophisticated and cohesive. The black penny loafers are essential here, echoing the black elements above and creating that sandwich effect that makes the whole outfit feel intentional and balanced.
Bringing Preppy Back
Drawing inspiration from classic preppy style, this outfit embodies that effortless, refined casual aesthetic that never goes out of fashion. The foundation is an ivory cotton canvas chore coat that brings both structure and casual coolness to the look. The ivory color is softer and more sophisticated than stark white, creating a refined base that works beautifully with the other elements.
Underneath, an off-white t-shirt provides the perfect relaxed contrast to the more structured jacket. The slight tonal difference between the ivory and off-white adds subtle depth without being too obvious or contrived. This layering approach creates visual interest while maintaining the clean, preppy aesthetic that defines this style.
The classic light wash denim brings authentic Americana vibes to the outfit, and this is where the magic happens with the black penny loafers. Loafers with jeans is such a quintessential preppy move that instantly elevates casual denim from weekend wear to something you could easily wear to a nice lunch or casual evening out.
The navy baseball cap adds another classic preppy touch while providing practical sun protection, and the black loafers ground the entire look with their sophisticated presence. This combination proves that preppy style doesn’t have to be stuffy or overly formal—it can be relaxed, approachable, and thoroughly modern.
Tonal Summer Suit
This look demonstrates how to approach wearing a suit during warmer months while maintaining sophistication and comfort. The ivory twill suit is the perfect foundation for summer suit style—light enough to be comfortable in heat, yet substantial enough to maintain a polished appearance.
The key to making this tonal approach work is the sand-colored shirt, which provides just enough contrast to define the silhouette without being jarring. When working with colors this close in tone, texture becomes crucial. The sandy hue complements the ivory beautifully while adding warmth to the overall palette.
Here’s where the sandwich method really shines in formal wear. The black penny loafers provide the perfect anchor for this light, airy ensemble. They’re formal enough for suiting but relaxed enough for summer, and their dark presence prevents the outfit from feeling too ethereal or insubstantial. The contrast they create against the light suit is exactly what this look needs to feel grounded and intentional. A matching belt ties everything together, creating continuity between the upper and lower halves of the outfit.
Summer Business Casual
This final look represents the most conservative and versatile approach, perfect for professional environments where you want to look polished without being overly formal. The light gray hopsack sport coat serves as the ideal foundation—the hopsack weave adds texture and visual interest while the gray color remains neutral enough to work in virtually any business setting.
The crisp white button-up shirt is a timeless choice that creates clean contrast against the gray jacket. There’s something to be said for the power of a perfectly pressed white shirt—it instantly elevates any outfit and conveys attention to detail and professionalism. The key to achieving that perfect collar stand is using a collar support band, which might seem like a small detail but makes a significant difference in the overall polish of the look.
Classic charcoal trousers complete the ensemble, providing the perfect neutral base that allows the other elements to shine. Charcoal is one of those colors that works with everything, and these trousers bridge the gap between the lighter jacket and the dark shoes beautifully. In this more conservative look, I opted for visible socks, which is more appropriate for professional settings and creates a more traditional, polished appearance.
The black penny loafers are the perfect finishing touch for this business casual ensemble. They’re formal enough for the office but more relaxed than traditional dress shoes, striking exactly the right balance for modern business casual dress codes. This combination proves that you don’t need to sacrifice style for professionalism—the black loafers add a contemporary edge to an otherwise classic outfit.
About the Myrqvist Stenhammar II
These particular loafers are worth highlighting for their craftsmanship. The Stenhammar II is an apron-fronted penny loafer built on Myrqvist’s rounded, wider last number 21, finished with a thin half rubber sole. Designed in Stockholm and handcrafted in Portugal, they feature leather board heel caps, cork filling, and Goodyear welted construction.
Available in multiple options including box calf (which I chose), dark brown and black suede, dark brown calf, and black country calf, these shoes offer excellent quality at their price point.
The Bottom Line
Even experienced menswear guys, like me, sometimes struggle with new pieces. The key is to keep experimenting and practicing. I spent an entire morning putting together these five looks—it wasn’t magic, just persistence and creativity.
Whether you’re dealing with black penny loafers or any other challenging piece in your wardrobe, remember to try the sandwich method, don’t be afraid to experiment with different color combinations, and most importantly, keep practicing. Put in the work, and you’ll see the results.
What’s your go-to method for styling challenging pieces? Share your tips in the comments below.
Thanks, as always, for reading.