Top 19 Old Money Outfit Ideas for Men

When it comes to fashion, the “old money” style is all about subtlety, classic tailoring, and quality over flashiness.

This look doesn’t shout wealth; instead, it quietly exudes sophistication and taste.

It’s about dressing in a way that reflects a legacy of timeless style and understated luxury. Here are 19 old money outfit ideas for men that embody the essence of sophistication and aesthetic.


1. Navy Blazer and Gray Trousers

A navy blazer paired with gray trousers is a quintessential old money look.

Choose a well-fitted blazer with a classic lapel and matching gray trousers in a fine wool fabric.

Add a crisp white button-down shirt, a silk tie, and polished brown leather shoes for a look that’s both elegant and timeless.


2. Tailored Tweed Suit

Tweed is a staple of old money style, known for its warmth and sophistication.

A tailored tweed suit with a soft-shouldered jacket and slim-cut trousers is perfect for cooler months. Pair it with a simple cashmere sweater or a dress shirt and a silk tie for an effortlessly classic look.


3. Polo Shirt and Chinos

For a more casual approach, a simple polo shirt in muted colors like navy, beige, or forest green, paired with chinos, offers a clean, relaxed yet refined look.

Choose well-fitted chinos, not too tight or loose, and classic loafers or boat shoes to complete the ensemble.


4. Cashmere Sweater and Wool Trousers

A fine cashmere sweater in a neutral tone (gray, navy, camel) paired with wool trousers gives a comfortable yet elegant look.

Opt for a slim fit sweater to keep it modern and pair it with brogues or oxford shoes for added sophistication.


5. Double-Breasted Suit

The double-breasted suit is a nod to traditional luxury and old-school masculinity.

Go for a well-tailored version in classic colors like charcoal, navy, or deep green. Pair it with a crisp white shirt, silk tie, and pocket square for a polished look.


6. Linen Blazer and White Shirt

A lightweight linen blazer is perfect for warmer months. Pair it with a white dress shirt and beige or gray trousers for a smart yet breathable look.

Leather loafers or suede driving shoes complete this summer-ready old money outfit.


7. V-neck Cashmere Sweater and Leather Loafers

For a refined casual look, pair a v-neck cashmere sweater with tailored trousers or chinos.

Finish it off with a pair of high-quality leather loafers, preferably in brown or oxblood, for an added touch of class.


8. Gray Suit and Black Leather Shoes

A classic gray suit never goes out of style.

Choose a medium to light gray suit with a tailored fit and pair it with a crisp white shirt and a silk tie. Black leather oxford shoes are the perfect finish to this polished and refined look.


9. Corduroy Blazer and Wool Pants

For a more textured and casual look, a corduroy blazer with wool trousers offers a perfect combination of comfort and sophistication.

Stick with earthy tones like brown, deep green, or navy. Pair it with a simple dress shirt or turtleneck sweater for a versatile look.


10. Wool Peacoat and Scarf

A wool peacoat is a classic outerwear piece that speaks volumes of understated luxury.

Opt for a well-tailored fit in navy or dark gray. Pair it with a simple cashmere scarf, wool trousers, and dress boots for a refined winter look.


11. Navy Suit and Brown Brogues

A navy suit with brown brogues offers a warm, rich contrast that feels elegant without being too stiff.

Add a light blue shirt, silk tie, and pocket square to enhance the timeless appeal of this combination.


12. White Dress Shirt and Khaki Trousers

A white dress shirt paired with well-tailored khaki trousers is one of the simplest yet most sophisticated outfits in the old money style. Opt for a lightweight cotton shirt and slightly tapered trousers to keep it modern. Pair it with leather loafers or derbies.


13. Suede Jacket and Cashmere Sweater

For a chic, slightly rugged look, pair a suede jacket with a soft cashmere sweater. This combination brings together comfort and sophistication with a touch of understated luxury. Add dark jeans or wool trousers and finish off with leather boots.


14. Plaid Wool Suit

Plaid wool suits, especially those in muted tones of green, gray, or brown, are another classic option for the old money aesthetic. Make sure the pattern is subtle and not overly bold. Pair with a simple shirt and tie, and polished brown leather shoes for a sophisticated look.


15. Cable-Knit Sweater and Slim Trousers

A cable-knit sweater, especially in a soft wool or cashmere fabric, paired with slim trousers offers a cozy yet elegant look. Choose neutral tones such as beige, navy, or charcoal, and finish the look with loafers or dress boots.


16. Blue Oxford Shirt and Khaki Shorts

In summer, a blue oxford shirt paired with tailored khaki shorts can give off an effortlessly polished vibe. Stick with high-quality materials and avoid overly casual looks. Boat shoes or loafers will elevate the outfit for a more refined touch.


17. Black Velvet Blazer and Dress Pants

For evening wear, a black velvet blazer paired with black dress pants is a luxurious and refined look. Keep accessories minimal, such as a simple black silk tie and a white pocket square. Black patent leather shoes will complement this elegant outfit.


18. Turtleneck and Wool Overcoat

A fine wool overcoat paired with a turtleneck sweater is both sleek and practical.

Choose a neutral-colored coat like camel or charcoal and pair it with a black or navy turtleneck. Slim-fit trousers and leather boots will complete this modern take on old money style.


19. V-Shape Sweater and White Shirt

For an elegant, streamlined look, opt for a v-shape sweater.

The simplicity of the outfit exudes sophistication. Keep accessories minimal and refined, such as a leather belt and polished shoes.


Final Thoughts

The old money style is not about flashy designer labels or bold patterns; it’s about embracing quality, classic tailoring, and understated elegance.

By choosing timeless pieces and focusing on fit and fabric quality, you can channel the effortless sophistication that defines this aesthetic.

Keep your wardrobe simple, refined, and built on key essentials, and you’ll embody the charm and grace of old money style.