This post shows 27 Timeless Old Money Outfit For Men in 2025
In a world of fleeting trends and ever changing fashion, some styles remain timeless, transcending eras with their elegance and sophistication. These styles belong to the realm of “Old Money.”
Rooted in tradition and understated luxury, the Old Money aesthetic is not about flashy logos or ostentation, it’s about quality, heritage and an effortless sense of refinement. Men who embrace this style exude confidence, class and an air of effortless wealth that is truly timeless.
In 2025, the Old Money Outfit For Men has gained renewed popularity, offering a refreshing alternative to the loud and fast fashion trends of the moment. This guide dives deep into 27 classic outfit ideas that will elevate your wardrobe and ensure you embody this enduring aesthetic.
If you’re dressing for a casual day out, a formal gathering or a weekend getaway, these outfit ideas celebrate the essence of Old Money style polished, sophisticated and forever in vogue.
27 Timeless Old Money Outfit For Men In 2025
1. The Navy Blazer and Khaki Trousers Combo
This quintessential Old Money outfit for men is a staple that embodies elegance and practicality. A tailored navy blazer paired with well-fitted khaki trousers creates a sharp yet relaxed look.
Opt for natural fabrics like wool for the blazer and cotton or linen for the trousers. Complete the ensemble with a crisp white dress shirt and brown leather loafers. This look is perfect for brunch at the country club or an afternoon yacht outing.
2. Crisp White Oxford Shirt with Beige Chinos
A crisp white Oxford shirt is the cornerstone of any Old Money wardrobe. Pair it with beige chinos for a look that’s understated yet sophisticated as an Old Money Outfit for Men
Roll up the sleeves for a casual vibe or keep them buttoned for a more polished appearance. Leather moccasins and a brown braided belt add the perfect finishing touch.
3. The Classic Double-Breasted Suit
A double-breasted suit in a neutral color like charcoal gray or navy blue screams Old Money elegance. This style of suit has been a hallmark of wealth and sophistication for decades.
Wear it with a silk tie, a pocket squar and polished leather oxfords to complete the look. It’s an impeccable choice for formal occasions or business meetings.
4. Cashmere Sweater with Wool Trousers
For a relaxed yet luxurious outfit, pair a soft cashmere sweater with tailored wool trousers. This Old Money Outfit For Men is ideal for cooler months, exuding a cozy yet sophisticated vibe.
Stick to neutral colors like camel, gray or navy for both pieces. Loafers or brogues work well as footwear.
5. Polo Shirt and Pleated Shorts
The combination of a fitted polo shirt and pleated shorts is a timeless summer staple for the Old Money aesthetic. Choose a high quality polo shirt in a classic color such as navy, white or pastel blue.
Pair it with tailored pleated shorts and finish with boat shoes or leather sandals. A leather watch adds an extra touch of refinement.
6. Three Piece Suit in Earthy Tones
Earthy tones like olive green, brown and tan are iconic in Old Money wardrobes. A three piece suit in these shades adds a vintage touch to your ensemble.
Pair it with a crisp dress shirt and a silk tie. Leather brogues or monk strap shoes are the ideal footwear to round out the look.
7. Turtleneck with a Tailored Coat
For winter sophistication, layer a fitted turtleneck under a tailored coat. Opt for rich fabrics like wool or cashmere for the coat and ensure it’s impeccably tailored.
This look exudes understated luxury and pairs beautifully with slim fit trousers and leather Chelsea boots.
8. Striped Dress Shirt with Suspenders
Suspenders are a subtle yet impactful detail in Old Money style. Pair a striped dress shirt with tailored trousers and classic suspenders for a look that’s both vintage and polished. Add leather oxford shoes and a gold tie clip to elevate the outfit further.
9. Tweed Jacket with Corduroy Pants
A tweed jacket instantly conveys a sense of heritage and class. Pair it with corduroy pants for a quintessential Old Money look.
Stick to earthy tones like forest green, brown or burgundy for the trousers. A pair of leather loafers or brogues completes this timeless ensemble.
10. Seersucker Suit
A seersucker suit is the ultimate summer staple in Old Money fashion. Lightweight and breathable, this suit in pastel shades like baby blue or cream is perfect for garden parties or summer weddings. Pair it with a white dress shirt, a silk tie and suede loafers for a polished finish.
11. Trench Coat Over a Suit
A high quality trench coat is a must-have in any Old Money wardrobe. Worn over a tailored suit, it creates a look of effortless sophistication.
Opt for classic beige or khaki tones and pair with polished leather dress shoes. This outfit is perfect for rainy day business meetings or formal events.
12. Crisp Linen Shirt and Tailored Shorts
Ideal for tropical climates, a crisp linen shirt paired with tailored shorts exudes relaxed elegance. Stick to neutral colors like white, beige or light blue for both pieces. Add leather espadrilles or boat shoes to complete the look.
13. Argyle Sweater Vest with Slim-Fit Trousers
An argyle sweater vest paired with slim fit trousers is a nod to preppy Old Money style. Choose muted colors for the vest and pair it with a white dress shirt underneath. Leather loafers and a sleek watch enhance the overall aesthetic.
14. The Monochrome Ensemble
A monochrome outfit in shades of gray, navy, or beige creates a sleek and sophisticated look. Pair a well-fitted blazer with matching trousers and a shirt in a slightly lighter or darker shade.
Add leather dress shoes to complete this Old Money Outfit For Men.
15. Velvet Blazer with Black Trousers
A velvet blazer is a statement piece that oozes luxury. Pair it with tailored black trousers and a crisp white dress shirt for formal occasions. Add a silk pocket square and patent leather shoes for a dashing finish.
16. Rugby Shirt and Slim Jeans
A rugby shirt paired with slim fit jeans is a casual yet polished Old Money look. Choose a high quality shirt in classic colors like navy and white. Leather loafers or brogues add a refined touch to this outfit.
17. Checked Blazer with Neutral Trousers
A checked blazer adds character to your outfit without being overly flashy. Pair it with neutral trousers and a plain shirt to balance the look. Brown leather monk strap shoes complete the ensemble.
18. Lightweight Knit Sweater with White Pants
A lightweight knit sweater paired with white pants creates a breezy yet polished look for spring or summer. Stick to pastel or neutral tones for the sweater. Loafers or boat shoes are the ideal footwear choice.
19. Button Down Shirt with a Silk Scarf
Adding a silk scarf to a button down shirt is a simple yet effective way to elevate your outfit. Pair it with tailored trousers and leather loafers for a sophisticated look that embodies the Old Money aesthetic.
20. Double-Breasted Blazer with White Pants
A double-breasted blazer paired with white pants creates a nautical-inspired Old Money outfit for men. Stick to navy for the blazer and add brown loafers or boat shoes to complete the look.
21. Knit Polo with Slim Trousers
A knit polo shirt paired with slim trousers offers a refined take on casual wear. Choose high quality fabrics and stick to neutral tones. Leather moccasins add the perfect finishing touch.
22. Pinstripe Suit
A pinstripe suit is a timeless piece that exudes power and sophistication. Choose classic colors like navy or gray and pair with a white dress shirt, silk tie and leather oxfords.
23. Quilted Jacket with Dark Denim
A quilted jacket paired with dark denim is a casual yet elegant look for cooler months. Add a cashmere scarf and leather Chelsea boots for a polished finish.
24. White Dress Shirt with a Tailored Waistcoat
A tailored waistcoat adds depth to a simple white dress shirt. Pair with slim fit trousers and leather brogues for a sophisticated Old Money look.
25. Wool Overcoat with Dress Pants
A wool overcoat is a staple for winter sophistication. Pair it with tailored dress pants and polished leather shoes. Add a cashmere scarf for extra warmth and style.
26. Chambray Shirt with Khakis
A chambray shirt paired with khakis creates a casual yet polished Old Money outfit for men. Roll up the sleeves for a relaxed vibe and add leather loafers to complete the look.
27. Classic Black Tie Attire
Nothing exudes Old Money sophistication like a classic black tie outfit. A tailored tuxedo, a crisp white dress shirt, a black bow tie, and patent leather shoes create a timeless and elegant look for formal events.
The Old Money aesthetic for men is not just a fashion statement; it’s a lifestyle rooted in tradition, quality, and sophistication. These 27 timeless outfit ideas prove that elegance never goes out of style. By investing in high-quality pieces and focusing on classic designs, you can create a wardrobe that stands the test of time.
If you’re dressing for a casual day out or a formal evening event, these Old Money Outfit For Men ideas ensure you’ll always look polished and refined. Embrace the art of understated luxury and let your style speak volumes about your impeccable taste.
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