Feature image for the blog post 'Old Money Aesthetic Outfits: From Summer to Winter', showcasing a young man in all-white attire walking down a street with a briefcase and blazer, set against a background of palm trees and an old money style car.

Old Money Aesthetic Outfits: From Summer to Winter

When it comes to timeless elegance and sophistication, few styles can match the allure of the old money aesthetic. This article guides you through the world of old money outfits, providing insight into both summer and winter styles while emphasising the importance of quality and craftsmanship.

From the basics of old money fashion to the fine details that make each season unique, this comprehensive guide aims to equip you with the knowledge you need to embrace the old money aesthetic. Here's a quick summary of what we'll be covering:

  • Explore the timeless elegance of old money outfits, highlighting specific style cues for both summer and winter seasons.
  • Discover the foundation of classic old money fashion, characterised by subtle luxury, attention to detail, and superior craftsmanship.
  • Learn how to curate your old money summer style, featuring key garments such as linen shirts and dresses, feminine sundresses, and tasteful accessories.
  • Dive into old money winter style, focusing on investments in outerwear, luxurious knitwear, tailored trousers and skirts, and winter accessories.
  • Navigate the old money shopping landscape, with a focus on timelessness, craftsmanship, and intricate details.
  • Understand the distinction between new money and old money aesthetic, emphasising the old money values of understated elegance, heritage, and lasting quality.

With that brief overview, let's delve deeper into the intricacies of old money outfits, beginning with the foundational principles that define this timeless aesthetic.

A young man wearing all white walking down the street holding a briefcase and blazer over his shoulder, palm trees and an old money style car in the background.

The Foundation: Classic Old Money Outfits

To begin our journey into old money style, let us first understand the basics. Old money fashion is all about looking refined, elegant, and timeless. For a comprehensive analysis, you can refer to our guide to old money fashion and aesthetic, which provides an in-depth look at how to get started with this classic aesthetic. In essence, old money outfits are about subtle luxury, intricate details, and excellent craftsmanship.

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Firstly, a well-tailored suit or dress is essential. Your wardrobe should have a mix of both casual and formal wear. Timeless pieces like button-down shirts, tweed jackets, and tailored trousers form the basis of versatile old money summer and winter wardrobes, as explained in our article on old money outfits for every season. The key is to choose garments made from quality materials and to focus on fit and comfort. For a deeper exploration into essential pieces that epitomise this aesthetic, check out our Old Money Wardrobe Essentials guid

"Old money style is not about flaunting wealth, but about understanding the importance of craftsmanship, quality, and tradition."
A well-dressed man in a shirt and shorts laying on a sunbed.

Old Money Summer Style

With the foundation in place, it's time to explore specifically for the warmer season. The old money summer style is all about maintaining a polished and sophisticated look while staying cool and comfortable during the hottest months.

  1. Linen shirts and dresses: In an old money summer wardrobe, linen garments are a must-have. Lightweight and breathable, linen helps you stay cool while looking effortlessly chic. Pair a classic white linen shirt with tailored shorts or a pleated skirt for the perfect summer ensemble.
  2. Feminine sundresses: Consider investing in a lovely sundress with an understated floral print or a pastel-coloured wrap dress for those garden parties or afternoon tea events. Include items with timeless details such as lace, pearl buttons, or delicate embroidery.
  3. Sophisticated summer accessories: Complete your old money summer outfits with tasteful accessories such as a straw hat, leather sandals or loafers, and a timeless tote or structured handbag.

When summer events demand a touch of formality, elevate your style with insights from our detailed breakdown of Old Money Event Dressing: From Casual to Gala Events. For further inspiration, check out our article on iconic old money styles, which explores several distinct looks that epitomise the old money aesthetic.

Woman in silk scarf and sunglasses, exemplifying old money style aesthetic.

Old Money Winter Style

As the mercury drops, old money outfits adapt seamlessly, focusing on cosy yet sophisticated garments that provide an air of refinement. Here are some essentials for the perfect old money winter wardrobe:

  1. Invest in outerwear: Classic wool coats or tweed jackets are essential winter wardrobe items. Opt for neutral colours such as navy, camel, or black to ensure versatility and timelessness. For a little extra panache, consider a chic cape or faux fur collar that exudes old money elegance.
  2. Luxurious knitwear: Update your wardrobe with high-quality cashmere or merino wool sweaters in understated colours. Cable-knit patterns, turtlenecks, and V-necks are all elegant options that can effortlessly enrich your winter style.
  3. Tailored trousers and skirts: Choose well-fitted wool trousers or long, pleated skirts to form the foundation of your old money winter outfits. Pair them with classic button-down shirts, turtleneck sweaters, or chic blouses for a refined and polished look.
  4. Winter accessories: No old money winter wardrobe is complete without a collection of exquisite accessories. Keep warm and stylish with plush scarves, leather gloves, berets, or elegant fedoras.
"Quality over quantity is the essence of old money fashion. Luxurious materials, impeccable fit, and timeless style are worth the investment."
Attractive young woman dressed in old money winter fashion, including a blazer, turtleneck, and gloves.

Old Money Shopping Guide

Finding the perfect old money fashion brands and garments can initially seem daunting, but our old money shopping guide can help you navigate through the world of effortless sophistication. Additionally, our collection of quality old money fashion brands can assist you in locating standout pieces to upgrade your wardrobe.

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When shopping for old money outfits:

  • Prioritise timelessness: Opt for classic cuts, high-quality materials, and neutral tones that withstand fleeting fashion trends.
  • Pay attention to craftsmanship: Invest in clothes made by skilled artisans who have a keen focus on detail and quality.
  • The details make the difference: Embroidery, monograms, or subtle embellishments can enhance an outfit's old money aesthetic.

By embracing and incorporating the old money aesthetic, you set yourself apart with refined elegance and timeless style. Whether you're curating versatile summer outfits or bundling up for winter, the lasting appeal of old money fashion is the epitome of sophistication.

1980s Ralph Lauren photoshoot showing a group of boys dressed in old money winter style, preparing for a game of tennis.

New Money vs. Old Money Aesthetic

While both new and old money lifestyles are associated with affluence, the way wealth is showcased and the values adopted significantly differ. Let's explore the key contrasts between new and old money aesthetic:

  1. Understated elegance versus conspicuous consumption: Old money fashion focuses on quiet sophistication, with an emphasis on quality, timeless cuts, and luxurious materials. On the other hand, new money often gravitates toward extravagance, embracing bold designer logos and attention-grabbing trends.
  2. Heritage and tradition versus modern trends: The old money aesthetic is rooted in history and longstanding traditions, valuing craftsmanship, and heirloom pieces. In contrast, new money style often seeks the latest and most innovative designs and may disregard the importance of heritage.
  3. Investment in lasting quality versus frequent wardrobe updates: Old money wardrobes stand the test of time, as they invest in curated, high-quality garments that last for years, while new money is more likely to constantly update their wardrobe with the latest trends.
"Old money aesthetic respects the past, treasures quality, and curates a wardrobe that tells a timeless story."
Elegant old money styled couple sitting on a car in front of a grand old money mansion.

As you transition your wardrobe from summer to winter and explore the world of old money fashion, remember the core principles that define this timeless aesthetic. Embrace understated elegance, cherish tradition, and invest in high-quality garments that never go out of style.


In conclusion, old money outfits offer a refined and sophisticated take on fashion, proving that lasting charm and elegance reside in the details and values adopted. Whichever season you find yourself in, the timeless appeal of old money style – both in summer and winter ensembles – majestically endures. With our comprehensive guides on old money fashion, style, and shopping, the world of classic sophistication is now at your fingertip

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