Today, we give you five Southern preppy outfit ideas for summer, inspired by Thomas, a 25-year-old rising star in the venture capital world.
As an alumnus of Vanderbilt University and avid golfer, Thomas is no stranger to preppy fashion but always felt: “It’s a bit too pretentious for relaxed summers.”
For Thomas, we curated five modern summer outfits inspired by the dressing style of Preppies who live in the American South, particularly North Carolina, South Carolina, Georgia, and Virginia.
The nautical aesthetic of this Preppy style evokes a classy summer look synonymous with success, sophistication, and an aura of Old Money.
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 we created for Thomas and see how each look can elevate your style:
1. Regatta Outfit
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-coloured linen trousers from Incotex, renowned for exceptional fit and comfort.
Layer a cream-coloured cable-knit cotton sweater from Ralph Lauren over your shoulders for a preppy touch.
Accessorise 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. Garden Party Outfit
Embrace the vibrant colours 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 the old-money summer style.
Pair the coat with a light blue cotton oxford shirt from Gitman Vintage and white linen trousers from Zanella.
Accessorise 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 epitomises the art of fine shoemaking.
This ensemble is guaranteed to turn heads at any summer garden party or outdoor soirée.
3. Tennis Club Outfit
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-coloured lightweight wool tennis sweater from Fred Perry over your shoulders for a touch of vintage style.
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.
Accessorise 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. Equestrian-inspired Look
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.
Accessorise 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. Country Club Outfit
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 double-breasted suit with a crisp white cotton dress shirt from Turnbull & Asser, known for impeccable craftsmanship.
Add a touch of colour 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.
Southern Preppy Outfits Do’s and Don’ts
To ensure you nail the old money summer style, keep these do’s and don’ts in mind:
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Capturing the essence of old money in summer outfits can be achieved easily with Southern preppy garments, footwear, and accessories that prioritise 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.
Styling Beyond Southern Preppy Fashion
Knowing some tips about the Southern Preppy style is just a small step towards dressing like a successful, confident gentleman.
True fashion mastery lies in knowing and matching your body shape/type with your seasonal colour – skin, eye, and hair colours.
It requires understanding how to shop and pair the most ideal garments, footwear, and accessories from the most relevant, heritage brands.
This is paramount to being able to dress correctly by body shape, occasion, location, time of the day, and lifestyle.
Find Your Body Shape
Different garments flatter different physiques so discover your body shape now by taking our free body shape quiz for men.
Identify Your Best Colors
Fashion comes in a wide range of colours, but not every hue will complement your natural colouring so find out your ideal colours with our free seasonal colour quiz for men.
Then, learn how to dress by occasion, location, season, and even time of the day.
Dress for the Occasion
Understanding how to choose and style garments from relevant heritage brands, and style them by occasion, season, location, and body shape is crucial.
From casual weekends to formal events, each occasion requires a unique approach to styling.
To save time, headaches, and even money, get in touch with The VOU’s expert stylists now.
Get Expert Styling Advice
Take our comprehensive fashion style analysis for men, and let our expert stylists guide you in selecting and curating items of maximum impact in a wardrobe that communicates success and confidence.
Remember, owning luxury brands isn’t enough. To look stylish, confident, wealthy, and successful you must match your body shape, colour palette, season, occasion, location, time of the day, to perfection.
With these tools and expert guidance, you’ll not just wear the brand—you’ll master it, creating a wardrobe that truly reflects a unique fashion taste and many achievements.
Get in touch with our team of pro stylists and receive a free summer wardrobe overhaul – it’ll be designed around the Southern preppy charm.
We’ll teach you how to recognise, 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.