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Old Money Summer Style Mastery with Southern Preppy Outfit Ideas

Today, we’ll introduce five Southern preppy-inspired summer outfit ideas to master the Old Money look.

The article is inspired by a client we styled last June, Thomas, a 25-year-old rising star in the venture capital world.

As an alumnus of Vanderbilt University and an avid golfer, Thomas was no stranger to preppy fashion but always felt that “it is a bit too pretentious for relaxed summers.”

Together, we curated five unique summer outfits that exuded elegance and confidence – the ones we present in this article.

The impact on Thomas’s professional and social life was remarkable – he closed three major deals and received countless compliments on his polished yet super relaxed appearance.

Let’s explore the five quintessential old-money summer outfits I created for Thomas and see how each look can elevate your style:

1. The Weekend Regatta

Channel the spirit of the sea with a nautical-inspired outfit perfect for weekend sporting events or a casual stroll along the marina.

Start with a classic navy and white Breton striped cotton jersey shirt from the French heritage brand Saint James.

Pair it with stone-colored linen trousers from Incotex, renowned for exceptional fit and comfort.

Layer a cream-colored cable-knit cotton sweater from Ralph Lauren over your shoulders for a preppy touch.

Accessorize with a handcrafted leather boat shoe from Sperry Top-Sider, a brand that has been a staple of nautical fashion since 1935.

Top off the look with a timeless Panama hat from Lock & Co. Hatters, a British institution crafting fine hats since 1676.

2. The Garden Party Soirée

Embrace the vibrant colors and patterns of summer with a garden party-inspired outfit.

Start with a tailored Madras plaid sport coat from the American prep icon J.Press.

The patchwork-like pattern, which originated from the Indian city of Madras (now Chennai), is a quintessential element of old-money summer style.

Pair the coat with a light blue cotton oxford shirt from Gitman Vintage and white linen trousers from Zanella.

Accessorize with a woven leather belt from Torino Leather Co. and classic tortoiseshell sunglasses from Anglo-American Optical.

Complete the look with a pair of brown suede tassel loafers from Edward Green, a brand that epitomizes the art of fine shoemaking.

This ensemble is guaranteed to turn heads at any summer garden party or outdoor soirée.

3. The Tennis Club Championship

Embrace the sporty side of old money style with a tennis-inspired outfit that exudes a sense of casual elegance.

Start with a crisp white performance polo shirt from Lacoste, a brand with a rich tennis heritage.

Pair it with tailored white tennis shorts from Fila, a company that has been at the forefront of tennis fashion for over a century.

Layer a cream-colored lightweight wool tennis sweater from Fred Perry over your shoulders for a touch of vintage charm.

Complete the look with a pair of classic white leather tennis sneakers from Adidas Stan Smith, a timeless silhouette that has graced the courts since the 1960s.

Accessorize with a subtle leather wristband from Miansai and a pair of tortoiseshell clubmaster sunglasses from Ray-Ban.

This outfit is perfect for a day at the tennis club championship or a casual summer brunch with friends.

4. The Equestrian Escapade

Channel the sophistication of the equestrian lifestyle with an outfit that seamlessly blends style and functionality.

Start with a classic white cotton polo shirt from La Martina, a brand deeply rooted in the polo world.

Tuck it into a pair of tailored beige jodhpurs from Polo Ralph Lauren, the epitome of equestrian-inspired fashion.

Add a touch of British elegance with a navy blue wool hacking jacket from Hackett London.

Complete the look with a pair of handcrafted brown leather riding boots from Ariat, a brand renowned for exceptional craftsmanship and attention to detail.

Accessorize with a classic leather belt from Hermes—featuring the iconic H buckle—and tortoiseshell aviator sunglasses from Persol.

This ensemble is perfect for a day at the polo fields or a countryside escapade.

5. The Country Club Luncheon

Start with a light blue seersucker suit from the iconic American brand Brooks Brothers for a refined look that is suitable for both the office and the country club.

The lightweight, striped cotton fabric is a hallmark of Southern summer style.

Pair the suit with a crisp white cotton dress shirt from Turnbull & Asser, known for impeccable craftsmanship.

Add a touch of color with a silk pocket square in a complementary pastel hue from Drakes London.

Complete the look with brown leather tassel loafers from Alden, a brand synonymous with timeless elegance.

This ensemble exudes an air of understated sophistication, perfect for a country club luncheon or a business meeting on a warm summer day.

Dos and Don’ts

To ensure you nail the old money summer style, keep these do’s and don’ts in mind:

Do’s Don’ts
  • Opt for well-tailored, classic silhouettes
  • Wear classic accessories like leather wristwatches and aviator sunglasses
  • Invest in high-quality, natural fabrics like cotton, linen, and silk
  • Stick to neutral colors and preppy patterns
  • Avoid trendy or flashy clothes and footwear
  • Steer clear of garish colors or prints
  • Don’t mix too many patterns in one outfit
  • Avoid loud logos or branded garments

Capturing the essence of old money in summer outfits can be achieved easily with Southern preppy garments, footwear, and accessories that prioritize quality, fit, and timeless elegance.

With these five outfit ideas and following the do’s and don’ts, you should be able to project an image of success and refinement.

Elevate Your Old Money Summer Style with The VOU

With our team of pro stylists, we’ll curate a summer wardrobe that exudes Southern preppy charm and timeless sophistication.

We’ll teach you how to recognize, purchase, and wear the best garments, footwear, and accessories for you, ensuring that you look and feel your absolute best.

Find your unique style with The VOU’s fashion style analysis today and embark on a journey of sartorial discovery.

Until next time, stay stylish, stay cool, and remember: summer is a state of mind, and you’re the master of your destiny.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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