14+ Recommended Old Money Outfits Men Will Love to Try

There’s an allure to the timeless elegance of old money fashion that captivates the senses. Picture yourself in outfits that whisper sophistication and exude confidence. What follows is a journey through styles that evoke a sense of classic charm and understated luxury.

1. The Classic Navy Blazer

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The navy blazer is a cornerstone of old money fashion. Its versatile nature makes it perfect for a casual lunch or a formal event. Pair it with crisp white shirts and khakis for a look that’s both relaxed and refined.

What makes it unique is its adaptability. You can dress it up with a tie or keep it casual with jeans. It’s an investment piece that never goes out of style, offering endless outfit possibilities.

Consider choosing a blazer with gold buttons to add a touch of opulence. Prices can vary, but a good-quality blazer is always worth the expenditure.

2. Tailored Gray Suit

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A gray suit is the epitome of elegant simplicity. It speaks volumes without saying a word and is ideal for any formal occasion. Choose a light gray for daytime events or a darker shade for the evening.

Its benefit lies in its neutrality, allowing you to pair it with a variety of shirt and tie combinations. The fit is key; make sure it’s perfectly tailored to your body for that polished look.

While a tailored suit might cost more, the confidence it brings is priceless. Opt for classic cuts that will remain stylish for years.

3. Oxford Button-Down Shirt

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An Oxford shirt is a wardrobe staple that exudes understated elegance. It’s versatile enough to be worn under a blazer or on its own with rolled-up sleeves.

The unique texture of the fabric offers a touch of sophistication. Choose classic colors like white or light blue for maximum versatility.

Invest in shirts that fit well around the shoulders and chest. You can find quality options at various price points, making it easy to add a few to your collection.

4. Cashmere Sweater

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There’s nothing quite like the feel of a cashmere sweater. It’s soft, luxurious, and perfect for layering. Wear it over a collared shirt for a preppy look.

The uniqueness of cashmere lies in its ability to keep you warm without added bulk. Choose neutral colors like camel, gray, or navy for maximum pairing potential.

Though cashmere can be costly, it’s an investment in comfort and style. Take care of it properly and it will last for years.

5. Leather Loafers

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Leather loafers are the quintessential old money footwear. They offer a balance of comfort and style, perfect for both formal and casual settings.

The benefit of loafers is their easy slip-on nature, combining convenience with elegance. Opt for classic colors like brown or black.

A good pair of loafers may require a bit of investment, but the durability and timeless style they provide make them worth every penny.

6. Trench Coat

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A trench coat is an iconic piece that adds a layer of sophistication to any outfit. It’s perfect for rainy days or cool evenings.

What sets it apart is its classic design and functionality. Choose a length that suits your height and complements your wardrobe.

While high-quality trench coats can be pricey, they offer protection against the elements while keeping you stylish.

7. Chino Pants

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Chino pants are a versatile wardrobe essential. They’re perfect for both casual and semi-formal occasions, offering comfort with style.

Their uniqueness lies in their adaptability. Pair them with a blazer for a smart look or a simple T-shirt for a relaxed vibe.

Chinos are available in a variety of colors and price points, making them a flexible addition to any wardrobe.

8. Wool Overcoat

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A wool overcoat is a must-have for the colder months. It adds a touch of elegance to any outfit and keeps you warm.

The benefit of a wool overcoat is its durability and timeless style. Choose classic colors like black, gray, or navy.

Though the initial cost can be high, a well-made overcoat is a worthwhile investment that will last for many winters.

9. Silk Pocket Square

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A silk pocket square is a small accessory that makes a big impact. It adds a splash of color and personality to your ensemble.

The uniqueness lies in its ability to elevate a simple suit. Choose patterns and colors that reflect your style.

Pocket squares are relatively inexpensive, allowing you to experiment with different styles without breaking the bank.

10. Argyle Sweater Vest

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An argyle sweater vest offers a preppy yet sophisticated look. It’s perfect for layering over shirts and under blazers.

The pattern is unique and eye-catching, adding a touch of character to your outfit. Opt for classic color combinations for timeless appeal.

Vests are a cost-effective way to enhance your wardrobe, providing warmth and style in one package.

11. Brogue Shoes

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Brogue shoes are a classic choice that adds a touch of flair to any outfit. Their detailed design is both stylish and functional.

The unique perforations set them apart from other dress shoes. Pair them with suits or chinos for a polished look.

Though they can be pricey, their durability and timeless style make them a valuable addition to your shoe collection.

12. Tweed Jacket

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A tweed jacket is synonymous with timeless elegance. It’s perfect for adding texture and warmth to your outfit.

The benefit of a tweed jacket is its versatility. Wear it with jeans for a casual look or over a shirt and tie for something more formal.

Tweed jackets come in various colors and patterns, allowing for personalization. They’re a smart investment for a stylish wardrobe.

13. Wool Scarf

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A wool scarf is both practical and stylish. It provides warmth while adding a splash of color or pattern to your outfit.

The uniqueness of a wool scarf lies in its ability to transform a simple coat into a fashionable statement. Choose colors that complement your wardrobe.

Scarves are affordable and can be easily switched up to match different outfits, making them a versatile accessory.

14. Corduroy Trousers

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Corduroy trousers are a comfortable and stylish option for cooler weather. Their textured fabric adds visual interest to your look.

The benefit of corduroy is its warmth and durability. Pair them with sweaters or blazers for a classic autumn ensemble.

Available in various colors, corduroy trousers are reasonably priced, making them a great addition to any wardrobe.

15. Leather Belt

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A leather belt is a simple yet essential accessory. It ties your outfit together while providing a touch of sophistication.

Choose high-quality leather for durability and a classic buckle for timeless appeal. It’s a small detail that makes a big difference.

Leather belts come in various price ranges, allowing you to find one that fits your budget and style.