Bentley Caldwell

NOVEMBER 2023: An Ode to Old

Each month Nashville #1 Men’s Personal Stylist, Bentley Caldwell will weigh in on the latest trends and answer men’s styling questions. His partner in crime, Carson Love will share her style tips for women.


His Style: An Ode to Old

This month, I’ve had the privilege of once again styling the men’s issue, which we were fortunate enough to shoot at the b-e-a-utiful Cheekwood Estate & Gardens. While preparing for the shoot, the concept of the “old money aesthetic” was bouncing around my mind. For those unfamiliar with the term, the “old money aesthetic” favors quality over quantity, elegance over extravagance and heritage over hurry-up. In today’s column, we’ll talk about what the old money aesthetic is in menswear, why it’s important and why you shouldn’t follow trends.

The Old Money Aesthetic in Menswear

To understand the old money aesthetic, you must understand old money. “Old money” refers to significant generational wealth. Think: the Rockefellers, the Vanderbilts, the Schermerhorns and whoever the family is that owns the color blue. Old money is wealth that stands the test of time. The same is true for the old money aesthetic in menswear. It is defined by heritage garments made in timeless fabrics, like tweed, cashmere and fine wool. Put simply, it is fashion that is made to last.

Why the Old Money Aesthetic Matters

In a world where fast fashion (H&M, Zara and Shein) runs rampant and devastates the environment, slow fashion transcends trends and gets back to the humanity of well-crafted garments. The old money aesthetic evokes the themes of yesteryear, when garments were made by artisans through meticulous design and craftsmanship. The level of detail was bar none. And that garment could be traced back to the source of origin. Can the same be said of a boy band tee from Zara? (Speaking of, NSYNC, we need that world tour!)

Why You Should Not Follow Trends

The short answer: Because they’re forever changing. One season, it’s chunky sneakers. The next, it’s skinny jeans. Then, it’s oversized pants. Bentley hot take: Trends are meant to keep you buying into consumerism. I said what I said! Get off the consumerism merry-go-around. There’s a reason why fabric makers like Abraham Moon & Sons have been around since the 1800s and the “dad” shoes trend died off a few years ago. Trends are temporary. Style is forever.

Gents, ’tis the season for a nice tweed suit and a good bourbon. Pinky finger up? Your call. Be well, lads!