15 Old Money Dress to Impress Outfit Ideas

The “old money” style is one of the most elegant and sophisticated ways to dress to impress. Using this timeless aesthetic means you’ll always look polished, classic, and timeless. No matter what kind of event you’re attending, or whether you’re going on a business trip or going to a casual event, here are 15 old money outfit ideas that will help you feel and look good.

1. Classic Tweed Suit

An old-money look wouldn’t be complete without a tweed suit. Consider a well-tailored suit in a neutral color, such as gray or navy. You can pair it with a crisp white shirt, silk tie, and polished leather shoes for a more formal look. Put on a pocket square and some cufflinks to add a touch of elegance.

Pro Tip: To keep the look classic and not too garish, go for tweed suits that have a subtle pattern.

2. Tailored Blazer and Chinos

It’s easy to look sophisticated and versatile when you pair a tailored blazer with chinos. Choosing a navy or charcoal blazer and pairing it with khaki or grey chinos is the best option. Make the look complete by wearing a button-down shirt and loafers.

Pro Tip: For a contemporary, polished look, opt for a slim fit blazer.

3. Cashmere Sweater and Trousers

There is something cozy and sophisticated about a cashmere sweater and trousers combination. If you’re looking for a cashmere sweater with a rich color, try a V-neck or crew neck sweater in burgundy or forest green. It looks great paired with tailored trousers in a complementary color.

Pro Tip: To add a touch of refinement to your blazer, layer a silk pocket square on top.

4. Tuxedo with White Tie

An old money look would be wearing a tuxedo and a white tie for the most formal occasions. You’ll look good in a classic black tuxedo paired with a white tie, white shirt, and patent leather shoes. You can add a vintage touch by wearing a bow tie and waistcoat.

Pro Tip: To avoid bulk and sagging, make sure your tuxedo fits perfectly.

5. Flannel Suit

The cozy and stylish look of a flannel suit is ideal for cooler weather. A charcoal or grey flannel suit is the perfect complement to a button-down shirt and silk tie. Make your look complete by wearing a pocket square and brogues.

Pro Tip: Wintertime is the perfect time to wear flannel suits for their warmth and style.

6. Leather Jacket and Chinos

An old money look is given a modern spin with a leather jacket and chinos. Match your leather jacket with khaki or grey chinos to create a classic look. You can finish the look with a button-down shirt and a pair of loafers.

Pro Tip: Keep your silhouette sleek by opting for a leather jacket that fits slim.

7. Corduroy Blazer and Trousers

There is nothing more stylish and unique than a corduroy blazer and trousers set. You can pair a corduroy blazer with matching trousers in deep navy or forest green. To complete the look, add a button-down shirt and oxford shoes.

Pro Tip: The warmth and durability of corduroy make it an excellent fabric for fall and winter.

8. Wool Overcoat and Suit

It is a classic and timeless look to pair a wool overcoat with a suit. Combine a navy or gray wool overcoat with a matching suit. Complete your look with a button-down shirt, silk tie, and dress shoes.

Pro Tip: Wool overcoats are ideal for cooler weather, as they provide warmth and style at the same time.

9. Velvet Blazer and Trousers

There is nothing more luxurious and sophisticated than a velvet blazer and trousers set. Put on a velvet blazer in a deep shade of blue or burgundy, and pair it with matching trousers. The look is completed with a button-down shirt and loafers.

Pro Tip: Adding a touch of elegance and sophistication to evening events is achieved with velvet.

10. Linen Suit

For warmer weather, you can’t go wrong with a linen suit. With a button-down shirt and silk tie, pair a light grey or beige linen suit. The look can be completed with a pocket square and a pair of loafers.

Pro Tip: Linen keeps you cool and comfortable in the summer because it is a breathable fabric.

11. Tweed Blazer and Chinos

Adding a tweed blazer to chinos will make your outfit versatile and stylish. Try pairing a tweed blazer in navy or charcoal with khaki or grey chinos to create a tailored look. You can complete the look by wearing a button-down shirt and loafers.

Pro Tip: An investment piece like a tweed blazer is a great addition to your closet.

12. Leather Jacket and Suit

With a leather jacket and a suit, you can achieve an old money look that is both stylish and edgy. You can pair a leather jacket with a navy suit or grey suit with a classic black or brown leather jacket. The outfit can be completed with a button-down shirt and a pair of dress shoes.

Pro Tip: Leather jackets add a touch of rebellion to classic suits, making them great choices for nights out.

13. Corduroy Blazer and Chinos

When paired with chinos, a corduroy blazer is a unique and stylish look. You can pair a corduroy jacket with khaki or grey chinos in a deep navy or forest green color. To complete the look, pair the suit with a button-down shirt and loafers.

Pro Tip: The warmth and durability of corduroy make it an excellent fabric for fall and winter.

14. Wool Overcoat and Chinos

It is a classic and timeless look to pair a wool overcoat with chinos. Whenever you wear your overcoat, wear it with khaki or grey chinos. To complete the look, pair loafers with a button-down shirt.

Pro Tip: Wool overcoats are ideal for cooler weather, as they provide warmth and style at the same time.

15. Velvet Blazer and Chinos

You look sophisticated and luxurious in a velvet blazer with chinos. Match your velvet blazer with khaki or grey chinos and a deep blue or burgundy shirt. To complete the look, pair your button-down with loafers.

Pro Tip: Adding a touch of elegance and sophistication to evening events is achieved with velvet.

Conclusion

Adding a modern twist to classic styles is the key to dressing to impress with an old-money aesthetic. These 15 outfit ideas are sure to help you feel and look your best, whether you’re wearing a tweed suit, a tailored blazer, or a velvet blazer. You can create a truly timeless look by paying attention to details such as fit, fabric, and accessories.