Old money style, synonymous with the connotation of timeless elegance, understated sophistication, and effortless class. The very first encounter with this aesthetic took place in a summer visit to the Hamptons to an old friend’s family gathering.
Men in that group exuded refinement, their every feature finely put together in tailor-made blazers, crisp shirts, and perfectly worn loafers, looking as though they might last generations. It wasn’t about logos or flashy brands but about quality, simplicity, and tradition.
That weekend, I couldn’t help but admire how polished and intentional their style was. Every single piece looked like it had been well thought out, from the perfectly pressed chinos to the small monograms on their cufflinks. Inspired, I found myself wanting to incorporate some aspects of old money style into my wardrobe. I started with classic things like navy blazers and Oxford shirts and worked my way up to a timelessly collectible list of items that never go out of style.
I’ve come to appreciate how this style celebrates the idea of “less is more.” It’s not about chasing trends but about investing in high-quality, versatile pieces that reflect confidence and refinement.
Whether you’re heading to a casual brunch, a business meeting, or a formal event, these 25 old money outfit ideas for men will elevate your wardrobe and help you embody timeless sophistication.
And within this style guide, I’ll be sharing practical tips and inspiration on how to achieve that old money aesthetic, so you can dress the part and embody the charm of classic men’s fashion.
Why Explore Old Money Outfit Ideas for Men?
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Timeless Appeal
Old money fashion is rooted in tradition, ensuring that your wardrobe remains stylish no matter the trends.
Investing in timeless pieces saves money over time and keeps your look effortlessly sophisticated.
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Emphasis on Quality
This style values well-made clothing over fast fashion, prioritizing craftsmanship and durability.
Quality pieces not only last longer but also convey a sense of refinement.
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Versatile and Practical
Old money outfits are designed to work across various occasions, from casual gatherings to formal events.
A well-curated wardrobe reduces decision fatigue and ensures you’re always appropriately dressed.
25 Old Money Outfit Ideas for Guys
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Navy Blazer with Chinos
Pair a tailored navy blazer with beige chinos and a white Oxford shirt for a classic smart-casual look.
Perfect for both business casual settings and semi-formal events.
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Crisp White Polo with Khaki Pants
A fitted white polo shirt tucked into khakis is a preppy yet relaxed combination.
A go-to look for summer brunches or outdoor gatherings.
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Double-Breasted Suit in Charcoal Grey
A well-tailored double-breasted suit exudes power and sophistication.
Ideal for formal occasions or business meetings.
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Cashmere Sweater over an Oxford Shirt
Layer a lightweight cashmere sweater over a collared shirt, paired with tailored trousers.
Warm, stylish, and versatile for cooler seasons.
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Pinstripe Suit with Leather Oxfords
A pinstripe suit paired with polished leather oxfords is a statement of refined elegance.
Timeless and professional, perfect for formal occasions.
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Linen Shirt with White Trousers
A breathable linen shirt tucked into crisp white trousers creates a laid-back yet sophisticated summer look.
Comfortable and stylish for warm-weather events.
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Trench Coat over a Suit
Layer a tailored trench coat over your suit for a polished, weather-ready ensemble.
Combines functionality with timeless style.
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Rugby Shirt with Slim-Fit Jeans
A striped rugby shirt paired with dark slim-fit jeans is a casual nod to preppy fashion.
Great for relaxed weekends or casual outings.
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Turtleneck with a Blazer
A fitted turtleneck under a blazer creates a modern yet classic aesthetic.
Ideal for semi-formal dinners or cocktail parties.
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White Oxford Shirt with Navy Shorts
A white Oxford shirt tucked into tailored navy shorts is perfect for summer soirées.
Simple, clean, and effortlessly classy.
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Cable Knit Sweater with Corduroy Pants
A cream cable knit sweater paired with corduroy pants is a quintessential old-money winter look.
Combines warmth and texture for a cozy yet refined outfit.
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Monochrome Suit with Loafers
Choose a monochrome suit in beige or grey and pair it with sleek leather loafers.
Minimalistic and perfect for formal occasions.
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Quilted Jacket with Slim Trousers
A quilted jacket layered over a knit sweater and slim trousers strikes the perfect balance between casual and sophisticated.
Ideal for transitional seasons or outdoor events.
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Breton Striped Shirt with White Chinos
A navy-and-white striped Breton shirt tucked into white chinos is effortlessly nautical.
A timeless choice for coastal or summer settings.
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Blazer with a Silk Pocket Square
Elevate a classic blazer look by adding a silk pocket square in a complementary color.
Adds a subtle touch of personality to formal attire.
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Tweed Jacket with a Wool Scarf
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Pair a tweed jacket with a textured wool scarf for a vintage-inspired ensemble.
Perfect for autumn or countryside outings.
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Polo Neck Sweater with Wool Trousers
A fitted polo neck sweater tucked into high-waisted wool trousers is effortlessly chic.
Combines warmth with sophistication.
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Camel Coat over a Suit
A camel coat layered over a navy or charcoal suit is a classic winter look.
Timeless and practical for colder months.
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Tailored Vest with Dress Pants
A tailored vest worn with matching dress pants and a crisp shirt creates a dapper three-piece suit look.
Polished and perfect for formal dinners or events.
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Leather Jacket with a Roll Neck
A well-fitted leather jacket over a roll neck sweater adds a modern twist to the old-money aesthetic.
Edgy yet sophisticated.
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Plaid Blazer with Dark Denim
A plaid blazer paired with dark-wash denim creates a smart-casual ensemble.
Great for dinners or casual business meetings.
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Overcoat with a Suit and Tie
A classic overcoat layered over a suit and tie is a winter staple for formal occasions.
Combines warmth and style effortlessly.
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Pique Polo with Tailored Shorts
A pique polo tucked into tailored shorts is a refined yet relaxed summer look.
Ideal for casual outdoor events.
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Silk Tie with a Crisp White Shirt
A silk tie paired with a crisp white shirt and tailored trousers is timelessly elegant.
Perfect for weddings or high-profile meetings.
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Velvet Blazer with Dress Shoes
A velvet blazer in deep hues like navy or burgundy paired with leather dress shoes exudes luxury.
A statement piece for evening events or special occasions.
Old money fashion is more than a trend—it’s a way of life that celebrates quality, tradition, and timeless style. These 25 outfit ideas for men offer practical inspiration for building a wardrobe that reflects refinement and sophistication.
Whether you’re dressing for business, leisure, or formal events, these looks will ensure you’re always impeccably dressed.
