If you happen to chase the trends, dressing well can be a real challenge. Just think how many iterations jeans have gone through. One day we will look back on skinny jeans as this era’s stonewash.

The secret of the always-sharp wardrobe, then, is appreciating the looks that never go out of style. That’s the approach of Chad Kincaid, fashion director for PVH’s Heritage brands, Van HeusenIZOD and ARROW.

This Portland native and University of Oregon alum has made it his mission to keep those labels current yet classic. And he’s the latest distinguished gent to tackle our Style Questionnaire.

Name: Chad Kincaid
Current Residence: Brooklyn, New York and Northwestern Connecticut
Hometown: Portland, Oregon
Occupation: Fashion Director, PVH Heritage Brands

Describe your style in three words.
Classic Americana with a Rebellious Twist (see what I did there?)

Who had the biggest influence on your style?
Classic mid-century American male style icons—James Dean, Carey Grant, Marlon Brando, Paul Newman, Steve McQueen, etc.

If you could have one piece of clothing from your childhood, what would it be?
Either of my grandfathers’ World War II military fatigues.

What’s one thing you always remember when getting dressed?
I always like to have at least one vintage piece on me—as simple as a handkerchief, tie clip or belt, but sometimes something more impactful like a hat, a cool old shirt or leather jacket.

What are three pieces that every man should have in his closet?
A great fitting pair of dark denim, a chambray shirt, and a pair of classic leather lace-up boots—equally appropriate for wrenching in the garage, walking in the woods, or dressed up with a tie and jacket for a night on the town.

What’s one thing a man should do to improve his style?
Find a good tailor—fit is everything, and the most inexpensive items in your closet can look like a million bucks with a little nip and tuck.

Outside of the PVH brands, what stores or websites do you frequent?
Mr Porter, Union Made, RRL, J Crew, Levi’s, eBay.

What trend would you like to see disappear?

When you want to make a good impression, what do you wear?
A snappy hat tops off any outfit.

What’s one thing that is always worth splurging on?
Leather—whether it’s a pair of shoes, boots or a great jacket—take care of it and your grandkids will be able to enjoy it too.

Van Heusen is known for their shirts. Any tips for pairing with ties?
Have fun with mixing and matching patterns—just remember to balance the scale. Big pattern shirt, small pattern tie—and vice versa.

What’s the most promising trend this fall?
The endurance of American Heritage—as much as it may sound cliché, trends come and go but classics never go out of style.