Style Talk with Kirk Robert Chambers: Fall essentials, bucket hats and Moscot

Fall is that in–between moment when your wardrobe has to do a little more thinking. Mornings feel crisp, afternoons still carry some warmth, and the right outfit needs to move easily between the two. It’s not about reinventing your look but about adjusting the rhythm, layering smarter, playing with texture, and knowing when to trade linen for wool or suede for leather.

Style in this season isn’t only about what you wear, but how you think about getting dressed. It’s the time to rediscover pieces you’ve had for years and mix them with something new, to let materials and tones do the talking. Whether it’s the sunglasses you choose, the watch on your wrist, or the way you layer a shirt under a jacket, every detail adds a line to the story of how you move through this in–between season.

In our conversation with Kirk Robert Chambers, the photographer and style connoisseur shared his take on what defines a fall wardrobe. He gravitates toward simple, classic pieces. Think denim, loafers, crew-neck sweaters, and versatile outerwear. Accessories are essential: he favors well-crafted sunglasses from Moscot or American Optical, understated watches from Tudor or Omega, and a trusty leather weekender for weekend getaways. His approach to color and fabric leans toward earth tones, soft textures, and timeless classics, with the occasional pop of color, while hats, jackets, and functional bags form the backbone of his everyday autumn look.

We caught up with him for a fall #StyleTalk. Here's what we found out.

What’s your go-to fall look?

“Denim, loafers, crew neck sweater, trench coat or some type of outerwear piece.” - Kirk Robert Chambers

On the topic of fall staples, Kirk believes that chunky knits and flannels can be timeless if chosen carefully. He appreciates the right piece that blends classic style with a modern feel, though, as he notes, fit is everything.

Are chunky knits and flannel shirts timeless staples, or do you see them as overdone?

Kirk Robert Chambers: Depending on the type of knit or flannel, they can definitely have a “timeless” look, and I think the right piece can look cool and classic. I’m bigger guy so they don’t always work for me, but I’ve seen plenty of guys wear them well.

Favorite brand of sunglasses?

Kirk Robert Chambers: Oh man. Lots of good ones out there. I’ll probably go with Moscot or American Optical. Well made, been around for a long time, classic, and they have something for everyone.

Favorite brand of watches? The timepiece you trust to complement your fall wardrobe.

“I like very simple, classic, and understated watches. I’d look at Tudor or Omega. Some can be investment pieces, but there are a lot of good vintage finds out there that will complement your outfit better than any other accessory and won’t break the bank.” - Kirk Robert Chambers

You’re escaping to a cozy cabin for the weekend. What are you packing?

Kirk Robert Chambers: My Moore & Giles leather duffle weekender to pack all the goods. Inside the bag we’ll have some dark denim, boots, a couple of flannels and crew neck sweaters, a denim jacket, and a leather dopp kit. I’ll probably bring my guitar and a couple bottles of whiskey and tequila, as well.

When it comes to scents, he keeps things simple and sticks to a few trusted fragrances year-round like Le Labo’s Santal 33 and 80 Muze No. 16 his go-to choice for fall.

What’s your favorite fabric to wear when it’s chilly, and do you have a favorite brand?

Kirk Robert Chambers: Probably a cashmere sweater. I’ve got a mix of vintage and newer stuff. If you’re buying new and building up the sweater arsenal, Buck Mason has some good mid-price staples.

Do you have a favorite fall shoe brand or boot style you love wearing?

Kirk Robert Chambers: I’m all about loafers in the fall, and all year around since I live in South Carolina. Baudoin & Lange is probably my favorite loafer brands at the moment.

Is there a fall color palette you always gravitate toward, or do you experiment each year?

Kirk Robert Chambers: I don’t go too crazy on colors or patterns. Most everything I wear is pretty simple and earth tone. I love shades of brown, green, blues, grays, and soft texture or patterns. I will occasionally add some pieces that are brighter and more colorful, like pops of yellow or orange.

Do you have a go-to hat, scarf, or accessory that defines your autumn look?

“I love a good bucket hat in the fall.” - Kirk Robert Chambers

Which city or country, in your opinion, has the best fall street style?

Kirk Robert Chambers: I gotta go with London. I’m more of a classic dresser, and I feel like they do this very well. There are still plenty of unique, modern fits and styles on the streets, but I feel like a lot of the looks have an element or piece of a timeless and classic men’s tailoring. Also, London is one of my favourite cities and the autumn city backdrop is unmatched.

What’s your take on seasonal trends vs. timeless classics during fall?

Kirk Robert Chambers: Trends range on a broad spectrum. I definitely pay attention to them and it’s fun to see what people are gravitating towards season to season, but personally, I’m trying to simplify my wardrobe. I’m always asking myself “could I wear this outfit in 10, 20, 30 years from now?” If the answer is “no,” then I’ll likely steer away from partaking in that trend or buying that item that’s associated with it. It’s not always the case, but this is my opinion more often than not.

When it comes to seasonal inspiration, Kirk doesn’t tie his style to a specific event or tradition. Instead, he gravitates toward the charm of university life - the classic “back to school” aesthetic. He draws inspiration from Ivy League influences and campus looks that span the 1950s through the 1990s, eras that captured a certain sophistication he continues to reinterpret in his own way today.

Your everyday essentials. What three things do you never leave the house without in autumn?

Kirk Robert Chambers: A hat, a jacket or coat, and a tote.

Thank you Kirk for this lovely interview!

Pictures: Kirk Robert Chambers