20+ Old Money Outfits for Men That Define Quiet Luxury Fashion

Ever wonder why some men’s outfits never seem to go out of style? Old money fashion has been around for decades, showing us that simple can be classy. These timeless looks blend comfort with a touch of luxury.

In this article, I’ll share 20 examples of old money outfits for men that anyone can try. Did you know many of these classic styles were first worn by wealthy families over 100 years ago? You’ll discover how small details make these looks special without breaking the bank.

1. Vintage Elegance Meets Urban Cool

This brown suit ensemble perfectly captures old money elegance in an effortless way. The rich brown tones pair beautifully with the simple white undershirt and leather belt. The relaxed jacket creates a refined yet approachable look against the tan vintage car backdrop.

Have you ever wondered how such a simple color palette can look so sophisticated? The high-waisted trousers and quality leather shoes complete this timeless outfit. The stone building and cobblestone street enhance the old-world charm of this look. This style works for both casual outings and semi-formal occasions!

2. Green Polo and Tailored Chino Combination

The dark green polo paired with light gray trousers creates a distinguished look. The brown leather belt ties the outfit together perfectly. You might spot this combination at country clubs and weekend gatherings alike.

The white sneakers add a modern touch to this traditional style. A leather weekend bag sits nearby, ready for casual outings or short trips. This outfit demonstrates how versatility remains central to old money fashion traditions.

3. Coastal Chic with Stripes and Sunglasses

The light blue striped shirt paired with navy shorts creates that effortless summer look. The outfit balances casual comfort with refined style. The simple watch and dark sunglasses add just enough accessorizing without trying too hard.

Can you imagine strolling through historic districts in this ensemble? The relaxed fit of the button-down creates an air of confidence. This outfit shows how old money style isn’t about flashy logos or trends. It’s about quality basics in a timeless color palette.

4. Oversized Cream Knit and Wide-Leg Denim Statement

The cream ribbed sweater paired with relaxed blue jeans creates a timeless old money look. What stands out is how it balances comfort with understated elegance. The loose fit of both pieces gives that effortless wealthy vibe.

Have you ever noticed how this style has endured for decades? The quality materials speak volumes without flashy logos. The watch peeking from under the sleeve adds just enough sophistication. This combination works equally well for weekend brunches or casual Friday meetings.

5. Riviera-Ready Linen Look with Leather Accents

This all-white ensemble captures the essence of old money style perfectly. The crisp linen shirt with rolled sleeves pairs beautifully with matching trousers. The brown leather belt adds just enough contrast without breaking the clean look.

Picture yourself at a summer garden party in this refined outfit. The loose fit and natural fabrics create that effortless Mediterranean vibe. The dark leather accessories anchor the outfit with subtle sophistication. This timeless summer look never goes out of fashion.

6. Navy Bomber and Cream Separates for Country Weekend Style

The navy bomber paired with crisp white pants creates a timeless country estate look. The design features relaxed fit while maintaining elegance. This combination works for both casual weekend gatherings and semi-formal outdoor events.

The classic vintage car completes this old money aesthetic perfectly. The stone mansion backdrop reinforces the heritage feel of the outfit. The style achieves an effortless balance between comfort and sophistication.

7. White Shirt and Olive Trousers with Messenger Bag 

The clean white shirt paired with sage green pants creates a distinguished look. The black suspenders add structure without being flashy. The silver watch and messenger bag complete this refined style.

Look closely at how such simple pieces create a put-together appearance. The pleated pants and relaxed fit shirt show attention to detail. This outfit proves that old money style relies on quality basics rather than trendy items.

8. Tonal Cream Knitwear and Statement Sunglasses

The cream knit polo creates a refined yet relaxed look paired with light gray trousers. The half-zip collar adds just enough structure while keeping things casual. The brown leather belt offers a subtle contrast against the neutral tones.

Did you know this style originated from leisure activities of the wealthy class? The loose fit of both the polo and trousers gives this outfit its old money appeal. Round sunglasses and a calm pose complete this effortless style that works for various occasions.

9. A Parisian Preppy Campus Look

The green sweater over a crisp white collar creates timeless old money appeal. The relaxed white pants balance the structured top half. Next time you see this combination, remember its deep roots in collegiate tradition.

This outfit stands perfectly against the elegant stone building backdrop. The blue-striped sneakers add a modern touch to an otherwise traditional look. The whole ensemble speaks of quiet confidence rather than trying too hard.

10. Metropolitan Minimalism

The navy coat over a black turtleneck creates a timeless fall look. Gray trousers complete this refined outfit against the backdrop of stone columns. You’ll appreciate how this ensemble balances structure with wearability.

The clean lines and tailored fit speak to old money style traditions. A subtle watch peeks from beneath the sleeve, adding just enough detail. This outfit works for both business meetings and evening events. The architectural setting enhances the overall polished effect.

11. Nautical Elements That Endure

The classic boat outfit pairs a navy tee with light striped pants and a cream sweater. One highlight is the brown leather belt adding warmth against the cool colors. The simple gold necklace and sunglasses complete this effortless river look.

Can you imagine cruising past historic stone bridges while dressed so thoughtfully? This outfit works perfectly for summer social events on the water. The contrast between structured clothing and relaxed posture creates that distinctive old money feel.

12. Knitwear With Athletic Roots

The classic cricket sweater makes a perfect old money statement piece. The cream cable knit with navy and blue trim creates that timeless collegiate look. This style pairs effortlessly with simple blue jeans for a relaxed appearance.

Isn’t it fascinating how cable knit sweaters remain a staple in wealthy wardrobes? They bridge the gap between casual and formal with their structured patterns. White sneakers with gum soles complete this understated look that feels both comfortable and distinguished.

13. City Neutrals

This cream polo paired with tan trousers creates a refined summer look. The ribbed texture adds subtle interest while maintaining simplicity. The eye is drawn to the monochromatic palette against the ornate building backdrop.

What would you do with a space like this? The relaxed fit of both pieces balances casual comfort with old-money elegance. The historic architecture and luxury cars complete this scene of understated wealth.

14. Structured Shirt with Designer Accessories

The black button-down shirt paired with flowing white pants creates a striking look. A special touch is how this combination balances casual ease with refined style. The pearl necklace adds an unexpected elegance against the dark fabric.

Did you know this high-contrast approach has roots in Mediterranean old money style? The relaxed fit of the pants with a more fitted shirt shows classic proportions. Dark sunglasses and leather accessories complete this effortlessly polished appearance.

15. Ribbed Neutrals for Modern Minimalist Appeal

The beige ribbed sweater paired with gray jeans creates a timeless look. The outfit balances comfort with refined style. The neutral colors work together perfectly against the dark patterned background.

Look closely at how such a simple combination appears so put-together. The relaxed fit of both pieces gives off that effortless old money vibe. This look works for casual settings yet still maintains that quiet luxury appeal.

16. Sunset in Berlin

The black sweater over a crisp white shirt creates a timeless look against historic architecture. You can see how this outfit balances casual comfort with refined style. The combination appears polished in the right setting.

This look captures the essence of old money style – understated yet purposeful. The tan chinos add warmth to the classic black and white pairing. The sunset backdrop enhances the outfit’s sophisticated feel without excess.

17. Summer Staples For Warm Weather

The white polo paired with tan trousers creates a timeless summer look. The brown leather belt adds just enough contrast to tie everything together. Loafers without socks became a signature element of old money summer style.

This outfit works perfectly against the Mediterranean villa backdrop with its pool. The rolled pant cuffs and relaxed fit speak to casual luxury. One watch and no other accessories keeps the focus on quality basics.

18. Tonal Texture Play

This tan sweater paired with crisp white pants creates a timeless old money look. The layers work together – the ribbed texture over a white undershirt adds depth. The relaxed fit speaks of quiet confidence rather than flashy style.

Next time you see neutral colors together, remember their sophisticated appeal. The combination works in almost any setting, from casual cafes to upscale venues. The loose-fitting pants with a clean drape show attention to quality fabrics.

19. Tennis-Inspired White Ensemble with Neckwear Accent

This cream-colored outfit shows old money style at its finest. The white polo with black trim pairs perfectly with light trousers and a brown belt. The draped scarf adds instant sophistication without trying too hard.

Can you imagine the impression this makes at an upscale venue? The silver watch and dark glasses complete this refined appearance. The shopping bag suggests he’s adding to his timeless wardrobe. This outfit works for various social occasions.

20. Winter White Masterclass

The all-white ensemble creates a powerful statement of refined taste. The cable-knit sweater adds texture without being flashy. The brown leather bag and shoes provide just enough contrast against the cream outfit.

Did you know old money style often relies on fewer, better pieces? This look demonstrates that principle perfectly. The relaxed fit of the pants balances the structured sweater. Quality speaks for itself without excessive ornamentation.

Conclusion

Old money style embodies timeless elegance through quality basics and thoughtful combinations. These outfits demonstrate how simplicity often creates the most sophisticated impression.

Consider trying one element from these looks in your own wardrobe. Whether it’s a cable knit sweater or neutral trousers, small changes can refresh your style with timeless appeal.