15 Classic Old Money Outfits for Men: Timeless Style and Elegance

When it comes to fashion, old money style is synonymous with timeless elegance, sophistication, and a touch of conservatism. This style is not about following the latest trends but about creating a look that stands the test of time.

In this blog post, we will explore 15 classic old money outfits for men, each designed to exude a sense of refinement and class.

Whether you’re attending a formal event, a business meeting, or a casual gathering, these outfits will help you make a lasting impression.

Understanding Old Money Style

Old money style is often associated with the upper echelons of society, where wealth has been accumulated over generations.

This style is characterized by high-quality materials, classic designs, and a focus on fit and tailoring. The goal is to create a look that is both polished and understated, avoiding ostentatious displays of wealth.

1. The Classic Three-Piece Suit

Outfit Description:
A three-piece suit is a quintessential “old money” outfit. Comprising a jacket, vest, and trousers, this ensemble is perfect for formal events and business meetings. Opt for a navy or charcoal gray color, as these shades are timeless and versatile.

Key Elements:

• Jacket: Choose a well-tailored, single-breasted jacket with a notch lapel.
• Vest: A matching vest adds a touch of elegance and formality.
• Trousers: Ensure the trousers are well-fitted and have a clean, pressed crease.
• Shirt: A white or light blue dress shirt is a classic choice.
• Tie: Opt for a silk tie in a solid color or a subtle pattern.
• Shoes: Pair with polished black or brown leather dress shoes.
• Accessories: Add a pocket square, cufflinks, and a classic watch.

2. The Tweed Blazer and Chino

Outfit Description:
A tweed blazer paired with chinos is a versatile and sophisticated look. This outfit is ideal for semi-formal events or a day at the office.

Choose a tweed blazer in a neutral color like brown or gray, and pair it with khaki or navy chinos.

Key Elements:

• Blazer: Select a tweed blazer with a classic fit and a notch lapel.
• Chinos: Choose chinos in a complementary color, ensuring they are well-pressed.
• Shirt: A white or light blue dress shirt is a safe choice.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with brown or tan leather loafers.
• Accessories: Add a pocket square, cufflinks, and a leather belt.

3. The Cashmere Sweater and Dress Pants

Outfit Description:
A cashmere sweater paired with dress pants is a comfortable yet elegant option for a variety of occasions.

This outfit is perfect for a casual dinner or a relaxed business meeting. Choose a cashmere sweater in a neutral color like gray or navy, and pair it with black or charcoal dress pants.

Key Elements:

• Sweater: Select a high-quality cashmere sweater with a V-neck or crew neck.
• Dress Pants: Choose dress pants in a complementary color, ensuring they are well-fitted.
• Shirt: A white or light blue dress shirt can be worn under the sweater for added formality.
• Shoes: Pair with brown or black leather dress shoes.
• Accessories: Add a leather belt, a classic watch, and a pocket square.

4. The Tailored Trench Coat

Outfit Description:
A tailored trench coat is a timeless piece that adds a touch of sophistication to any outfit. This coat is perfect for a rainy day or a crisp autumn evening.

Choose a trench coat in a classic beige or khaki color, and pair it with a well-fitted suit or a smart casual outfit.

Key Elements:

• Trench Coat: Select a high-quality trench coat with a classic fit and a belt.
• Underneath: Choose a well-fitted suit or a smart casual outfit.
• Shirt: A white or light blue dress shirt is a classic choice.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with polished black or brown leather dress shoes.
• Accessories: Add a pocket square, cufflinks, and a classic watch.

Also Read: 15 Outfit Inspiration for Men: Elevate Your Style with These Fashion Tips

5. The Plaid Flannel Suit

Outfit Description:
A plaid flannel suit is a classic choice for a more relaxed yet sophisticated look. This outfit is ideal for a casual business meeting or a family gathering.

Choose a plaid flannel suit in a neutral color like gray or brown, and pair it with a simple dress shirt.

Key Elements:

• Suit: Select a well-fitted plaid flannel suit with a notch lapel.
• Shirt: Choose a white or light blue dress shirt.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with brown or black leather dress shoes.
• Accessories: Add a pocket square, cufflinks, and a classic watch.

6. The Cashmere Overcoat

Outfit Description:
A cashmere overcoat is a luxurious and elegant addition to any wardrobe. This coat is perfect for a cold winter day and can be paired with a variety of outfits.

Choose a cashmere overcoat in a classic color like black or navy, and pair it with a well-fitted suit or a smart casual outfit.

Key Elements:

• Overcoat: Select a high-quality cashmere overcoat with a classic fit and a belt.
• Underneath: Choose a well-fitted suit or a smart casual outfit.
• Shirt: A white or light blue dress shirt is a classic choice.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with polished black or brown leather dress shoes.
• Accessories: Add a pocket square, cufflinks, and a classic watch.

7. The Corduroy Blazer and Chinos

Outfit Description:
A corduroy blazer paired with chinos is a stylish and comfortable option for a variety of occasions.

This outfit is perfect for a casual dinner or a relaxed business meeting. Choose a corduroy blazer in a neutral color like brown or green, and pair it with khaki or navy chinos.

Key Elements:

• Blazer: Select a corduroy blazer with a classic fit and a notch lapel.
• Chinos: Choose chinos in a complementary color, ensuring they are well-pressed.
• Shirt: A white or light blue dress shirt can be worn under the blazer for added formality.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with brown or tan leather loafers.
• Accessories: Add a pocket square, cufflinks, and a leather belt.

8. The Leather Jacket and Dress Pants

Outfit Description:
A leather jacket paired with dress pants is a stylish and edgy look that can be dressed up or down.

This outfit is perfect for a casual dinner or a night out. Choose a leather jacket in a classic color like black or brown, and pair it with black or charcoal dress pants.

Key Elements:

• Leather Jacket: Select a high-quality leather jacket with a classic fit.
• Dress Pants: Choose dress pants in a complementary color, ensuring they are well-fitted.
• Shirt: A white or light blue dress shirt can be worn under the jacket for added formality.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with black or brown leather dress shoes.
• Accessories: Add a leather belt, a classic watch, and a pocket square.

Also Read: 15 Outfit Inspiration Black Women: Embrace Your Unique Style

9. The Tweed Sport Coat and Jeans

Outfit Description:
A tweed sport coat paired with jeans is a stylish and comfortable option for a variety of occasions.

This outfit is perfect for a casual dinner or a relaxed business meeting. Choose a tweed sport coat in a neutral color like brown or gray, and pair it with dark wash jeans.

Key Elements:

• Sport Coat: Select a tweed sport coat with a classic fit and a notch lapel.
• Jeans: Choose dark wash jeans in a slim or straight fit.
• Shirt: A white or light blue dress shirt can be worn under the sport coat for added formality.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with brown or tan leather loafers.
• Accessories: Add a pocket square, cufflinks, and a leather belt.

10. The Cashmere Cardigan and Chinos

Outfit Description:
A cashmere cardigan paired with chinos is a comfortable and elegant option for a variety of occasions.

This outfit is perfect for a casual dinner or a relaxed business meeting. Choose a cashmere cardigan in a neutral color like gray or navy, and pair it with khaki or navy chinos.

Key Elements:

• Cardigan: Select a high-quality cashmere cardigan with a classic fit.
• Chinos: Choose chinos in a complementary color, ensuring they are well-pressed.
• Shirt: A white or light blue dress shirt can be worn under the cardigan for added formality.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with brown or tan leather loafers.
• Accessories: Add a pocket square, cufflinks, and a leather belt.

11. The Wool Peacoat

Outfit Description:
A wool peacoat is a classic and versatile piece that adds a touch of sophistication to any outfit.

This coat is perfect for a cold winter day and can be paired with a variety of outfits. Choose a wool peacoat in a classic color like black or navy, and pair it with a well-fitted suit or a smart casual outfit.

Key Elements:

• Peacoat: Select a high-quality wool peacoat with a classic fit and a belt.
• Underneath: Choose a well-fitted suit or a smart casual outfit.
• Shirt: A white or light blue dress shirt is a classic choice.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with polished black or brown leather dress shoes.
• Accessories: Add a pocket square, cufflinks, and a classic watch.

12. The Herringbone Suit

Outfit Description:
A herringbone suit is a classic and elegant choice for a variety of occasions. This outfit is perfect for a formal event or a business meeting.

Choose a herringbone suit in a neutral color like gray or navy, and pair it with a simple dress shirt.

Key Elements:

• Suit: Select a well-fitted herringbone suit with a notch lapel.
• Shirt: Choose a white or light blue dress shirt.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with black or brown leather dress shoes.
• Accessories: Add a pocket square, cufflinks, and a classic watch.

Also Read: 15 Y2K Club Outfits: A Fashion Guide to the Nostalgic Era

13. The Tweed Suit

Outfit Description:
A tweed suit is a classic and sophisticated choice for a variety of occasions. This outfit is perfect for a formal event or a business meeting.

Choose a tweed suit in a neutral color like brown or gray, and pair it with a simple dress shirt.

Key Elements:

• Suit: Select a well-fitted tweed suit with a notch lapel.
• Shirt: Choose a white or light blue dress shirt.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with brown or black leather dress shoes.
• Accessories: Add a pocket square, cufflinks, and a classic watch.

14. The Cashmere Turtleneck and Dress Pants

Outfit Description:
A cashmere turtleneck paired with dress pants is a comfortable and elegant option for a variety of occasions.

This outfit is perfect for a casual dinner or a relaxed business meeting. Choose a cashmere turtleneck in a neutral color like gray or navy, and pair it with black or charcoal dress pants.

Key Elements:

• Turtleneck: Select a high-quality cashmere turtleneck with a classic fit.
• Dress Pants: Choose dress pants in a complementary color, ensuring they are well-fitted.
• Shirt: A white or light blue dress shirt can be worn under the turtleneck for added formality.
• Shoes: Pair with black or brown leather dress shoes.
• Accessories: Add a leather belt, a classic watch, and a pocket square.

15. The Leather Bomber Jacket and Chinos

Outfit Description:
A leather bomber jacket paired with chinos is a stylish and edgy look that can be dressed up or down.

This outfit is perfect for a casual dinner or a night out. Choose a leather bomber jacket in a classic color like black or brown, and pair it with khaki or navy chinos.

Key Elements:

• Bomber Jacket: Select a high-quality leather bomber jacket with a classic fit.
• Chinos: Choose chinos in a complementary color, ensuring they are well-pressed.
• Shirt: A white or light blue dress shirt can be worn under the jacket for added formality.
• Tie: A silk tie in a solid color or a subtle pattern adds a touch of formality.
• Shoes: Pair with brown or tan leather loafers.
• Accessories: Add a pocket square, cufflinks, and a leather belt.

Conclusion

Old money style is all about timelessness, quality, and a touch of elegance. Whether you’re dressing for a formal event, a business meeting, or a casual gathering, these 15 classic outfits will help you exude a sense of refinement and class.

By focusing on high-quality materials, classic designs, and a perfect fit, you can create a look that stands the test of time and makes a lasting impression.