This Is How You Can Rock the Old Money Aesthetic

by | Feb 20, 2024 | Style

Classic threads are getting an egalitarian makeover, blending timeless elegance with a touch of contemporary flair, creating ensembles perfectly suited for the sun-drenched days of summer. Here’s how to infuse your wardrobe with the essence of old-money sophistication, effortlessly prepping your look for the last stretch of summer and any other outdoor event/sitch you need to attend during the final days of summer.

The Power Blazer

A navy blazer is one of the most versatile garments you can add to your burgeoning collection of threads. Modern iterations of this ultimate enhancement feature contemporary two-button single-breasted cuts and elegant double-breasted options, too.

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Custom Fit Single Breast Blazer

Oxford Classic Shirt

Ray-Ban Black Andy Sunglasses

DENHAM Bandana

adidas SAMBA sneakers

Breitling Ford Mustang

Casual Layering

Layering is a skill every guy should master. Done right, you can add serious depth and dimension to any look. Try a lightweight jersey over a casual shirt, colour chinos and white sneakers.

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Polol Denim Shirt

Polo Chinos

Thule Aion Duffel

Sleeveless Cotton Vests

Denham Langford Crew Knit

Polo Socks

READ MORE: How To Pick The Best Board Shorts For Your Body Shape This Summer

Easy-To-Style Classic

There’s something so effortlessly chic about a sleeveless pullover. This iconic item works whether you’re dressing down for beachside drinks or dressing up for a night out. Pull this over a boxy white Tee or striped blue linen shirt to instantly take any look from good to great.

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Denham Lawrence Vest

Huawei GT 4 Watch

JacobsbyJacobs Necklace

Reebok Club C 85 Sneakers

Quality Over Quantity

A timeless aesthetic demands garments that are built to last. So, when you’re choosing a suit, shell out a little extra to make sure you’re getting the finest fabrics like merino wool, linen and cotton. 

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Trenery T-shirt

Zara Pants

Polo Belt

Bass & Co Larkin shoe

CHIMI Sunglasses

The Preppy Golfer

Back in the day, informal threads matched the sophistication of their formal counterparts. Borrow from history by donning a preppy polo shirt spun from breathable cotton. It’s understated but suave, and choosing a colour like pink will hammer home your confidence. Just stay away from anything too bright. 

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Trenery Golfer

Scotch & Soda Knit

Denham Razor Clean Denim

Old Money Sport

This new wave of active fashion has its roots in country club sports like tennis, golf and polo. But today’s ready-to-wear pieces won’t restrict you to the greens; most transition seamlessly from a social setting to settling scores while retaining their distinctive charm and nostalgic edge. Just make sure you snag the right fit.

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LV Signature Sunglasses

PUMA Luxe Sport Track Jacket

Puma Palermo Sneaker

Mesh Bracelet Evergold

READ MORE: 5 Classic Men’s Style Essentials That Will Stand The Test Of Time

Invest in Neutral

Stock up your wardrobe with neutral tones for threads that will let you adapt on the fly. Most of these chameleon-like layers can be paired with something suitably over the top (think: tropical hues). You’ll want to look for lighter tones like beige, white, off-white, grey, cream or tan.

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CHIMI Sunglasses

Louis Vuitton Trunk Bag

JacobsbyJacobs Necklace

Scotch & Soda Blazer

Scotch & Soda Pants


Fashion Director: Azeez Jacobs
Photographer: Teri Robberts
Fashion Editor: Wagheeba January
Model: Jackwin O’Reilly at Boss Models
Location: Flash Studios Cape Town

A version of this story appeared in the Nov/Dec 2023 issue of Men’s Health.

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