An outfit can be perfectly put together, but the wrong shoes can throw the whole thing off. Conversely, the right pair of shoes can elevate even the simplest look, grounding it with personality and style. Some actors have mastered this art, making their footwear choices seem completely effortless, yet incredibly impactful. Their go-to shoes become as much a part of their signature style as their acting roles.

These are not the flashy, flavor-of-the-month sneakers that dominate trend cycles. Instead, they are timeless, versatile, and durable classics that exude confidence. From rugged work boots to sophisticated loafers, these actors choose footwear that tells a story and only gets better with age. Let's walk through some of the most iconic footwear choices made famous by stylish actors and explore how you can make these classics a part of your own wardrobe.

Ryan Gosling’s Red Wing Moc Toes

Ryan Gosling has cemented his status as a modern style icon, known for his ability to blend classic Americana with a contemporary edge. While his style is versatile, one piece has become a consistent staple in his off-screen wardrobe: a pair of well-worn Red Wing Moc Toe boots. He’s been photographed in them for years, pairing them with everything from cuffed jeans and a simple t-shirt to a cardigan and chinos.

The Red Wing 875 Classic Moc Toe is a legendary American work boot, originally designed for farmers and factory workers in the 1950s. Its distinctive moccasin-style stitching and durable crepe sole make it instantly recognizable. Gosling’s affinity for these boots speaks to his appreciation for quality craftsmanship and rugged, masculine style. The boots look lived-in and loved, which is the whole point. They are not precious; they are meant to be worn. This choice reflects a confidence that isn't about looking perfect, but about looking authentic.

How to Style Them

  • The Go-To Casual Look: Take a cue directly from Gosling and pair your Red Wing Moc Toes with dark selvedge denim. Cuff the jeans just above the top of the boots to show them off. On top, keep it simple with a white henley or a vintage-inspired graphic tee. A classic leather or denim jacket completes this timeless, rugged look.
  • A Step Up: These boots can also work in a smart-casual context. Try them with a pair of olive or khaki chinos and a chunky-knit sweater or a casual button-down shirt. The key is to balance the boot's ruggedness with slightly more polished pieces.
  • Pro Tip: Don’t be afraid to beat them up. Red Wing boots are built to last and develop a unique patina over time. Every scuff and crease adds to their character. Invest in some quality leather conditioner to keep them healthy, but let them show the miles you've put on them.

Steve McQueen’s Desert Boots

Steve McQueen, the original "King of Cool," had a style that was effortlessly masculine and rebelliously understated. His wardrobe consisted of simple, timeless pieces that he wore with an unparalleled level of confidence. Among his most iconic footwear choices were his suede desert boots, specifically the Clarks model. He wore them both on and off-screen, most notably in films like Bullitt and The Great Escape.

The desert boot was originally designed for British army officers stationed in North Africa during World War II. Its simple, two-eyelet design, suede upper, and crepe sole made it lightweight and comfortable in hot climates. McQueen’s adoption of the boot helped transition it from military gear to a menswear staple. For him, the desert boot represented a casual, anti-establishment cool. It was less formal than a leather dress shoe but more refined than a sneaker, striking a perfect balance.

How to Style Them

  • Classic Cool: Channel McQueen by pairing brown suede desert boots with white or stone-colored trousers or jeans. A simple navy polo shirt or a slim-fit crewneck sweater on top creates a clean, sophisticated look that is pure 1960s cool.
  • Modern Versatility: Desert boots are incredibly versatile. They work just as well with dark denim as they do with tailored chinos. For a smart-casual office look or a date night, try pairing them with dark trousers, a button-down shirt, and an unstructured blazer.
  • Care is Key: Suede can be intimidating, but it’s easier to care for than you think. Invest in a suede brush and eraser to gently remove dirt and revive the texture. A protective spray can also help guard against water and stains, keeping your boots looking sharp for years.

Brad Pitt’s Laid-Back Loafers

Brad Pitt's style has evolved over the years, but he has settled into a look of relaxed, sophisticated cool. He often leans into a tonal, minimalist aesthetic, and his footwear choice frequently reflects that: the loafer. Whether he’s on a red carpet or walking through an airport, Pitt often opts for a pair of simple, comfortable loafers, usually in suede or soft leather.

The loafer is a slip-on shoe that perfectly balances comfort and elegance. Pitt’s preference for them showcases a man who values ease without sacrificing style. He chooses soft, unstructured loafers that feel more like slippers than dress shoes, reinforcing his laid-back, Southern California vibe. It’s a confident choice that says he doesn’t need to be constrained by laces or formal dress codes to look put-together.

How to Style Them

  • Relaxed Elegance: This is Pitt’s signature. Pair a pair of tan or brown suede loafers with light-colored linen trousers or relaxed-fit chinos. On top, go for a simple, high-quality t-shirt or a breezy, open-collar shirt. The entire look should feel soft, comfortable, and monochromatic or tonal.
  • With Denim: Loafers and jeans can be a great combination. Opt for a slim or straight-leg jean in a light to medium wash. A penny loafer in a classic brown or oxblood leather adds a touch of preppy sophistication to an otherwise casual outfit. Avoid wearing them with baggy or bootcut jeans.
  • To Sock or Not to Sock: This is a perennial debate. For the most part, loafers look best without visible socks, especially in warmer weather. If you’re not comfortable going sockless, invest in some no-show liner socks. In colder months, you can experiment with pairing loafers with high-quality wool socks for a classic, academic-inspired look.

The footwear choices of actors like Ryan Gosling, Steve McQueen, and Brad Pitt teach us a valuable lesson: iconic style is built on timeless classics, not fleeting trends. Their preferred shoes—work boots, desert boots, and loafers—are all versatile, durable, and packed with personality. They prove that you don’t need a closet full of shoes to be well-dressed. You just need a few high-quality, well-chosen pairs that you can wear with confidence.