No products in the cart.


No products in the cart.

Old Money Northern Preppy Style Guide for Classy Gentlemen

Today, we will explore the world of Northern Preppy style and how you can incorporate this timeless aesthetic into your winter wardrobe.

So, grab a hot toddy, and let’s start this sartorial journey!

Northern Preppy Style Origins

Before we delve into the specifics of crafting the perfect Old Money winter outfit, let’s take a moment to understand the roots of Northern Preppy style.

This aesthetic originates in the traditional Ivy League fashion of the Northeast United States, where cold weather and outdoor activities heavily influenced the clothing choices of the well-to-do.

The emphasis was on quality, timeless pieces that could withstand the elements and maintain their sophistication.

Northern Preppy Wardrobe Essentials

To achieve a Northern Preppy-inspired Old Money look for winter, you’ll need to curate a wardrobe comprising traditional essentials such as:

Garment Description
Wool Blazers & Sport Coats Well-tailored jackets in classic patterns like herringbone or tweed
Cashmere or Cable-Knit Sweaters Classic preppy colors like navy, forest green, and burgundy
Oxford Button-Down Shirts White or light blue OCBDs as a versatile foundation for any outfit
Corduroy or Wool Trousers Neutral colors like khaki, olive, or gray for maximum versatility
Leather Boots or Loafers Quality footwear that can withstand the elements and maintain their polish

Layering Style

Effective layering is one of the secrets to mastering the Northern Preppy winter look.

Start with a base layer, like a cotton undershirt or turtleneck, then add a sweater or vest, and top it off with a wool coat or jacket.

Don’t forget accessories such as cashmere scarves, leather gloves, and wool hats to add a unique flair to your ensemble.

Grooming Tips

In addition to your clothing choices, your grooming habits play a crucial role in achieving the Old Money aesthetic.

Opt for classic, neat, well-maintained hairstyles and avoid overly trendy or army-style haircuts.

If you sport facial hair, keep it trimmed and tidy; alternatively, go for a clean-shaven look.

During the winter months, moisturize your skin to combat dryness and maintain a healthy, polished appearance.

Northern Preppy Style Icons

Let’s take a look at some notable figures who have embodied the Old Money look for winter, over the years:

  1. John F. Kennedy – The epitome of East Coast prep, JFK’s winter style featured wool overcoats, turtleneck sweaters, and leather boots.
  2. Ralph Lauren – The designer is often seen sporting Northern Preppy essentials, such as cable-knit sweaters, corduroy trousers, and tweed jackets.

Northern Preppy Style Outfit Ideas

One of the beauties of the Northern Preppy winter look is its versatility.

With a few key pieces, you can create outfits suitable for a range of occasions:

Casual Weekends

For a relaxed casual weekend look, pair a cable-knit sweater with corduroy trousers and leather boots.

Top it off with a wool coat and a cashmere scarf for warmth and style.

Office Attire

To maintain the Old Money look professionally, opt for a wool blazer, Oxford shirt, and wool trousers.

A pocket square adds a pop of color, and polished loafers finish the outfit.

Formal Events

For dressier occasions, reach for a tailored suit in a rich, winter-appropriate fabric like flannel or tweed. Pair it with a crisp white shirt, a silk tie, and well-shined dress shoes.

Styling Tips

To ensure your Northern Preppy winter outfits exude the Old Money aesthetic, keep these tips in mind:


  • Invest in high-quality, timeless pieces
  • Focus on fit and tailoring
  • Experiment with layering different textures and fabrics
  • Accessorize with purpose (e.g., a vintage watch or a family heirloom)
  • Pay attention to grooming and personal hygiene


  • Follow fleeting trends or opt for overly flashy garments
  • Neglect the importance of proper fit
  • Overdo it with logos or branding
  • Forget the power of simplicity and understated elegance

Northern Preppy Brands

When building your Northern Preppy winter wardrobe, consider investing in pieces from these renowned brands:

  1. Ralph Lauren – The quintessential preppy brand, offering a wide range of winter essentials
  2. Brooks Brothers – A classic American label known for its high-quality tailoring and timeless style
  3. J.Press – An Ivy League staple, providing traditional menswear with a focus on craftsmanship
  4. Barbour – The British brand’s waxed jackets and quilted coats are perfect for the Old Money winter look
  5. Alden – Handcrafted leather shoes and boots that combine durability and elegance

Expert Styling at Your Fingertip

Congrats, you now have the knowledge and tools to create stunning Old Money winter outfits inspired by the Northern Preppy aesthetic.

Don’t stop here; take your Old Money style to the next level with The VOU’s expert styling packages.

Our seasoned professionals will work closely with you to curate a winter wardrobe that embodies the Old Money look while reflecting your unique personality and lifestyle.

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.

Similar Articles


Please enter your comment!
Please enter your name here

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.