Bentley Caldwell

OCTOBER 2023: Falling for Fall Spice

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: Falling for Fall

The crisp breeze through the auburn- and orange-colored trees, the crunching of leaves on the ground, and pumpkin spice everything — everywhere — can only mean one thing: Layering season is upon us!

With fall weather comes fall fashion! This is the most wonderful time of the year in menswear. Why? Because we get to layer and truly peacock with our wardrobe. Here are four items you need to help you strut your stuff this fall.


The dip in temperature beckons us to explore. For that, you’re going to need a boot that can withstand the rigors of the fall elements or, at least, the corridors of Nissan Stadium during Titans games — yikes. I suggest you splurge a little and get a nice pair of leather boots.

A good pair of leather boots will cost you between $300 and $600, whereas a stellar pair is a bit of an investment at $600-plus. Nothing compares to the comfort and quality of a pair of high-end leather boots. Trust me, they pay dividends for years to come. 


I cannot stress enough the importance of denim in a man’s wardrobe. Last month, I talked about jeans. This month, I’m throwing jackets and shirts into the mix. A good denim jacket or shirt is a fall staple, and it’s a workhorse in my wardrobe.

Dress up the jacket with a tie, button-up and dress pant for a different take on business casual, or sub in a denim shirt with your suit, instead of your typical dress shirt. The sky’s the limit!

Sweaters, Hoodies

Another big component of layering season is lightweight sweaters and hoodies. These are great pieces to toss on for crisp fall mornings or brisk autumn evenings. Personally, I opt for merino wool or cashmere: Both are lightweight, buttery soft and unbelievably comfortable. You’ll want to give yourself a hug!


Fall is not yet time to throw on the down parka, but it’s a little too chilly to go without what we call a “third piece.” This is where jackets reign supreme! Play with different fabrics here — like waxed canvas or corduroy — or go more premium with a suede or leather jacket. Layer your jacket with your favorite hoodie to keep you warm without the bulk.

This fall, remember, gents: Be bold, be brave and — most importantly — be 100 percent you! Until next time.