Top 5 Shoes Billionaires Wear (and Why)

Wandering around the yacht marina, first class lounge and Goodwood paddock, you quickly learn about the whispers of wealth, especially from the ankles down. The richest people in this room don’t need a logo to prove anything. They vote on materials, comfort, and context. Here are five silhouettes I see over and over again on millionaires and millionaires. We’ll show you what they represent, how they’re worn, and how to choose the right pair for your wardrobe.

1) Loro Piana Soft Suede Walker — a shoe that “disappears into the background”

What it is: Think Open Walk / Summer Walk — Buttery off-brand Italian suede on a flexible sole that’s quiet on marble or teak. The shapes are smooth rather than sharp, the palette is desaturated (tobacco, sand, shark gray), and the finish is matte. A few steps away and they almost disappear.

Why Billionaires Wear It:

• Complete stealth. The suede reads, “Private jet, not a press release.”
• A luxurious feel to the touch. The high-quality suede looks and feels like cashmere.
• Also suitable for travel. Slip-on for easy security. There is no need to wear shoelaces on paved roads.

How they style it:

• Chino pants with slim hems and wool pants with drawstrings. Long sleeve polo. Light cashmere zip hoodie. Blazer without lining.
• On deck: tailored linens, woven belts, and a watch that never makes a sound.

Purchase notes:

• Prefer split suede or reverse calf. The brushed finish will age beautifully.
• If you live near a sea breeze, use a suede protector before wearing for the first time and use a crepe brush weekly.
• If you’re looking for a more understated look, look for unbranded Italian mock-toe sole walkers in muted tones. The shape is more important than the name.

Signal: We’ve been so successful that we don’t need a logo.

2) On Cloud 5 / Performance Runners — “Loud and Quiet” Sneakers for the Yacht Deck

What it is: A lightweight Swiss-engineered sneaker with an instantly recognizable segmented sole. On the quays, white/grey, slate, black, etc. are everywhere. They’re high-tech, nimble, and unapologetically practical.

Why Billionaires Wear It:

• A story of comfort and technology. Private equity professionals love engineering stories as much as cushioning.
• Travel agility. Run from G650 to gate B12 without running-in.
• Status camouflage. To the untrained eye, they are just running shoes. In a crowd, they are a quiet flex.

How they style it:

• Technology pants (4-way stretch) with merino t-shirt and featherweight shell.
• Weekend uniform: Navy knit joggers, crisp white On Clouds, matte sunglasses, and a cross-body cell phone call it “practical.”

Purchase notes:

• Choose Cloud 5 or Cloud X for daily use. If you want a stealth millionaire vibe, avoid neon.
• Keep them spotless. Wash the shoelaces in the washing machine and wipe the sole grooves.

Signal: I like performance and can afford to optimize everything.

3) ZEGNA Triple Stitch — A strapless slip-on that means business

What it is: A laceless, elastic gusseted slip-on with Zegna’s signature triple cross-stitching on the tongue in materials including deerskin, grained calf and technical knit. A dressy sneaker alternative. Sophisticated, quiet and ideal for meeting rooms.

Why Billionaires Wear It:

• A quick and elegant entry. They slip on like loafers and look tailored and sharp.
• Soft and supple upper. The legs are made of deerskin and high quality calf mold.
• Logoliteracy. This three stitches is not a shout but a nod.

How they style it:

• Soft tailoring: unstructured jacket, knit tie and 5-pocket wool pants.
• Traveling: Navy blazer, black triple stitch, gray t-shirt – done.

Purchase notes:

• It has a loose fit. If you’re in between sizes, consider sizing down half a size.
• Prefer a leather-lined version for breathability. If you’re looking for maximum versatility, avoid bright contrast soles.

Cue: I sealed the deal over lunch and caught the 15:05 flight to Milan.

4) Tod’s Gommino & Loafers — “I own at least 5 pairs” uniform

Includes: Tod’s pebble-soled Gommino driver and classic penny/strap loafers in calf or suede. It is a perennial on superyachts because the driver can grab the teak and fold it into the luggage like a glove.

Why Billionaires Wear It:

• Consistency over decades. The pattern remains largely unchanged. That’s the point.
• Gentle on cheeks. Rubber pebbles = traceless traction.
• color library. From biscuits to navy to cigarettes, you’ll find them neatly lined up by the aisles.

How they style it:

• Driver: Linen shorts, clean polo shirt, discreet bracelet, salt spray hair.
• Loafers: cotton silk pants, OCBD, unlined safari jacket, soft leather weekender.

Purchase notes:

• Drivers aren’t built for marathon walks around town. The sole is thin. Get it from your car to your table by the day.
• If you rotate pairs and use cedar wood, you get the year, not the season.

Signal: My schedule runs on Riviera time.

5) Made to order, unbranded and handmade in Italy – the quietest power move of all

What it is: Shoes made to fit your foot shape by master craftsmen in Florence, Naples and Marche. There’s no logo or obvious branding, just your name engraved on the inside. Think hand-welted oxfords, woven loafers, split-toe derbies, whole-cut museum calfs, or soft bespoke slip-ons that look “ready to wear” until you measure your proportions.

Why Billionaires Wear It:

• Perfect fit. If you have unwieldy feet or simply want comfort, customization is the answer.
• Materials that cannot be purchased off-the-shelf. Museum calf, reverse kudu, rare suede, hand-dyed patina.
• Unflattering exclusivity. No one can imitate your last.

How they style it:

• Business: Handmade split-toe derby and high-twist navy suit in dark oak.
• Leisure: Unlined bespoke loafers and pleated linen trousers, suede overshirts.

Purchase notes (mainly Italy):

• Florence: artisans of the Stefano Boehmer school, workshops such as Roberto Ugolini, or traditional family laboratories producing for the great Maisons.
• Marche/Naples: A small atelier known for its hand-stitched uppers and supple construction.
• Expect a try-on, a few visits, and a relationship. This is a technique, not a checkout.
• Care: If you are walking around town, the shoe store will add creams, waxes, and rubber toppers.

Signal: I don’t buy status. I’m entrusting it.

How to choose like a millionaire (even if you’re not)

1) Prioritize silhouettes over logos. The eye first reads shapes: the gentle almond toe of Loro Piana’s Walker, the structured sole of On, the balanced proportions of ZEGNA slip-ons, the neat apron of Tod’s loafers, the harmony of bespoke lasts. If your shape is correct, your clothes will be correct.

2) Live with a neutral palette. Tobacco, sand, stone, navy, shark gray, dark oak. These tones work well with linens, cashmere and technical fabrics and look great in any light.

3) Once purchased, always maintained. Cedar shoe trees, suede protectors, and good shoe stores keep up with the trends. Rotate pairs. Let the leather rest. The wardrobe of the wealthy is smaller than you think, just well-edited.

4) Wear shoes suitable for the road surface. Teak wood and car day driver. Running sole sneakers for airports and hilly cities. Sophisticated slip-ons with soft tailoring. A suede walker for every place in between.

5) The fit is true luxury. If you’re between sizes, talk to a suitable fitter or consider having it made to order. No amount of padding can fix a bad last.

Quick pairing and situational guide

• Jet Day (carry-on only): Cloud 5, tech pants, soft-shoulder blazer, merino t-shirt.
• A board meeting that turns into dinner: ZEGNA triple stitch, unstructured suits and knit ties.
• Yachting Weekend: Tod’s Gommino in tobacco suede, white denim and open weave polo.
• Long lunch in Tuscany: shark gray Loro Piana walker, pleated linen pants and suede belt.
• Night in the Black Car: Bespoke split-toe derbies in dark brown museum calf, navy suits and crisp white shirts.

The Tell: How Wealth Really Appears Under Your Feet

• silence. Expensive shoes don’t click. they glide.
• Maintenance without mania. Freshly polished suede, nourished calf, never a mirror shine, even in brunch.
• Contextual fluency. Billionaires wear shoes that are appropriate for their environment. That’s taste and respect.

TL;DR: The Five

1. Loro Piana Soft Suede Walker – Ultra-stealth luxury for everyday life.
2. On Cloud 5 / Performance Runner – Premium technology comfort.
3. ZEGNA Triple Stitch – A laceless polish for suiting and soft tailoring.
4. Tod’s Gommino & Loafers – Riviera uniform. I own several.
5. Bespoke, unbranded, made in Italy – quiet at its finest.

When you manage these five lanes, you don’t have to shout, you speak the language of modest wealth.