30+ Old Money Winter Outfits 2023 You’ll Love

As the winter chill settles in and the holiday season approaches, it’s time to elevate our style game and embrace the elegance of “Old Money Winter Outfits.” Picture yourself strolling through a winter wonderland, exuding timeless sophistication and class with your sartorial choices.

From luxurious coats to statement accessories, we’ve got all the inspiration you need to rock that classic, opulent look. So, let’s delve into the world of timeless fashion and discover how to stay cozy and chic during the chilly months ahead!

30+ Old Money Winter Outfits

Old Money Aesthetic and Style

Get excited about the timeless and sophisticated old money aesthetic! Inspired by the fashion choices of classic socialites and icons such as Jackie Kennedy Onassis, Paul Newman, and Lady Diana, this style exudes understated elegance and charm with a touch of American prep.

As you dive into the old money style, remember to prioritize classic, versatile pieces made from high-quality materials. Your wardrobe essentials should include tailored pants, a crisp white button-down shirt, cashmere sweaters, and structured blazers. Accessories can play a significant role in achieving the look, so consider adding silk scarves, leather gloves, stylish brooches, and timeless handbags to complete your outfit.

To master the old money aesthetic during winter, focus on layering various textures and elegant patterns. Opt for luxurious fabrics like cashmere, wool, and leather and high-quality outerwear such as trenches, pea coats, and fur-trimmed parkas. This ensures that you look elegant and stay warm and cozy throughout the season.

Integrating old money fashion into your lifestyle, take inspiration from the American prep style by incorporating preppy patterns like plaid, houndstooth, and argyle. Don’t be afraid to mix tailored pieces alongside more casual garments, like pairing a polished blazer over a crisp polo shirt or sweater. Embrace a polished yet relaxed vibe while maintaining your old money flavor.

Essential Old Money Items

Old Money Winter Outfits

Trousers and Blazers

Trousers: When it comes to winter outfits, functional yet fashionable trousers are a must. Beige trousers, for instance, are versatile piece that can be easily paired with a variety of tops and shoes. They’ll keep you warm and stylish throughout the season.

Blazers: A well-fitted blazer can elevate any outfit to new heights. Opt for a classic cut and colors like navy or black, which can seamlessly blend into your winter wardrobe. A blazer can be layered over a blouse or a turtleneck for added warmth and class.


A beautiful coat is the backbone of any winter wardrobe. A wool coat in particular, such as a camel coat, is a timeless piece that will keep you warm and add polish to your outfit. Here are a few options for chic winter coats:

  1. Classic Trench Coat – This versatile coat can be easily styled with dresses, jeans, or trousers, adding sophistication to any outfit.
  2. Faux Fur Coat – Stay cozy and stylish with a glamorous faux fur coat, perfect for dressing up a simple ensemble.
  3. Plaid Coat – A plaid coat adds a touch of pattern to your wardrobe and pairs well with solid-colored clothing items.

Black Dresses

When it comes to old-money winter outfits, a black dress is a wardrobe essential. This versatile garment can be dressed up or down depending on the occasion. A winter-appropriate version would be a long-sleeve black dress, which offers warmth as well as elegance. Pair it with tights, knee-high boots, or stylish heels for any elegant gathering or dinner party.

Top Brands for Old Money Style

Ralph Lauren is a true classic in the world of old money style. They offer a wide range of clothing items, including luxurious cashmere sweaters, elegant coats, and timeless accessories, perfect for your winter wardrobe. Embrace the Ralph Lauren look and feel like royalty as you walk down the street, bundled up in their finest pieces.

Lacoste is another brand synonymous with the old money vibe. Known for their signature polo shirts, they also offer an excellent selection of high-quality knitwear and outerwear that radiate comfort and class. Stay warm and stylish with a chic Lacoste scarf or a well-tailored coat, the perfect addition to your winter outfit.

Luca Faloni is a luxurious Italian brand that focuses on crafting beautiful cashmere and leather products. Their designs showcase the epitome of old money elegance, with a subtle touch of European sophistication. Invest in a Luca Faloni cashmere sweater or a timeless leather belt to elevate your outfit and add an air of opulence to your winter ensemble.

Selecting the Perfect Old Money Color Palette

Regarding old money style, neutral colors are your best friends. These classic shades exude elegance and allow you to create versatile, easily mixed, matched outfits. Consider beige, black, and shades of gray as your base.

Oh, and don’t forget about muted tones! Incorporating colors like dusty rose, deep burgundy, and forest green will add depth to your winter wardrobe without overpowering the overall aesthetic. These subtle hues work wonderfully when paired with your neutral staples.

For a quick reference, here’s a list of fantastic colors for an old money winter outfit:

  • Classic black
  • Crisp white
  • Alluring beige
  • Rich navy
  • Moody gray
  • Dusty rose
  • Deep burgundy
  • Forest green

Accessorizing Your Old Money Outfit

Footwear Essentials

Step up your shoe game with the perfect footwear essentials to complete your Old Money aesthetic! Loafers are an absolute must-have for both men and women in this style. These classic, timeless shoes provide comfort and add a touch of class to your outfit. Opt for high-quality materials like leather, suede, and find colors that match your outfits, like black, brown, or navy. Don’t forget that a well-polished pair of loafers goes a long way in showcasing your sophistication!

Jewelry and Watches

Adorning your outfit with the right accessories can make all the difference. For an Old Money vibe, choose timeless and understated jewelry pieces such as a delicate necklace or a simple pair of stud earrings. Stick with precious metals like gold, silver, or rose gold to exude an air of affluence and elegance.

Keeping time in style is essential for that Old Money look. Invest in a classic, high-quality watch that matches your overall aesthetic. Both vintage and modern watches can work, as long as they have an air of sophistication and elegance. Brands like Rolex, Cartier, and Patek Philippe are examples of luxury timepieces that embody the Old Money style. Remember, less is more when accessorizing your winter outfit, so choose your jewelry and watches wisely, and you’ll be exuding that excited, Old Money charm effortlessly.

Dress Like Old Money on Social Media

Old Money Winter Outfits

Ever dreamed of dressing like old money, but not sure where to start? Look no further! You can now create the perfect old money winter outfits with these stylish tips, while also rocking your TikTok presence. Here are a few essential tips to help you achieve this unique, sophisticated, and exciting aesthetic outfit look:

Choose Classic Colors and Patterns: One of the keys to old money outfits is sticking to timeless colors and patterns. Think neutral shades like black, navy, and beige, as well as classic patterns like plaid or houndstooth. These colors and patterns never go out of style and can be easily mixed and matched for endless possibilities.

Invest in Quality Pieces: Forget fast fashion! Old money outfits are all about high-quality, timeless garments that will last for years to come. So, splurge on well-made, luxurious fabrics (think wool, cashmere, and silk) and focus on staple items like tailored coats, blazers, and classic knits.

Accessorize Wisely: A signature accessory can elevate your old money aesthetic outfit. Consider a vintage silk scarf, an elegant watch, or even a fabulous brooch to add some wow factor to your winter look. Just remember, less is more when it comes to old money style.

Take Inspiration From Style Icons: To truly embrace the old money vibe, learn from the best! Study the fashion choices of timeless style icons like Audrey Hepburn, Grace Kelly, or even modern-day royals like Kate Middleton. Incorporate some of their classic pieces into your wardrobe and let their elegance shine through in your TikTok videos.

Achieving the Ideal Sophistication Level

First, invest in some classic outerwear. A well-fitted wool or sophisticated trench coat will instantly elevate your winter wardrobe. Opt for neutral colors like black, navy, or camel, as these shades add a touch of refinement to any outfit. Remember, quality is key when it comes to old money style, so choose garments made from durable, luxurious materials.

Your winter wardrobe should also include some tailored trousers and elegant skirts. Opt for high-waisted, wide-leg trousers in rich fabrics like wool or tweed, which can be paired with chic silk or cashmere sweaters. Similarly, pleated or A-line skirts also work perfectly with fitted dress shirts or turtleneck sweaters. The combination of these pieces creates a subtle yet sophisticated look.

Accessories play an essential role in completing your old money look. Add a classic leather belt to accentuate your waist and silk scarves in bold patterns to elevate your ensemble. Don’t forget about polished leather boots or loafers that showcase impeccable craftsmanship – footwear can make or break an outfit!

Incorporate rich, textured fabrics like cashmere, velvet, and brocade into your winter outfits to exude luxury and sophistication without being overly flashy. These materials not only look and feel expensive, but they also provide much-needed warmth during the colder months.

Finally, the old money look emphasizes subtlety and restraint, so avoid over-accessorizing or choosing flashy, trendy pieces. Stick to one or two statement items at most – less is often more when it comes to this style.


How do you dress old money in the winter?

Old money dresses elegantly in the winter, favoring timeless and luxurious pieces like cashmere coats, wool blazers, fur-lined gloves, and classic designer scarves. They use neutral colors, fine fabrics, and understated accessories to exude sophistication and refinement.

How to dress to look like old money?

Wear classic, high-quality clothing in neutral colors to look like old money. Opt for tailored suits, cashmere sweaters, pearl necklaces, and timeless accessories. Keep a polished appearance with well-maintained grooming and subtle elegance to exude an aura of sophistication and wealth.

How does old money actually dress?

Old money typically dresses in understated, high-quality clothing, favoring classic pieces from renowned designers. They opt for tailored suits, fine fabrics, and timeless accessories, exuding an air of effortless elegance and sophistication without flaunting their wealth.

What are old money clothes called?

Old money clothes are often referred to as “preppy” or “traditional” attire. These include classic and timeless pieces like tailored suits, cashmere sweaters, pearl necklaces, and designer accessories, reflecting a refined and elegant style associated with long-standing wealth and social status.

What Colours are old money style?

Old money style often features neutral and muted colors. Classic hues like navy, camel, gray, and ivory are popular choices for clothing and accessories. These colors exude sophistication, refinement, and timelessness, reflecting the understated elegance associated with old money fashion.

How can I dress better without breaking the bank?

To dress better without breaking the bank, focus on thrifting, shopping during sales, and investing in versatile, timeless pieces. Mix and match existing items, explore affordable fashion brands, and prioritize fit over brand names. Accessorize strategically to elevate your look without overspending.

Disclosure: We only recommend products we would use ourselves and all opinions expressed here are our own. This post may contain affiliate links that we may earn a small commission at no additional cost to you.

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Founder & CEO of Streetstylis

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