Jon Scott Bennett

02/08/2025

28/06/2025

The Highlands Surveyor

Shirt: This Banana Republic tunic was picked up at a yard sale in Beacon. What immediately struck me was, of course, its vibrant orange color. According to the seller, he had last worn it on an ill-fated expedition through Constitution Marsh, which ended with him capsizing and scaring some exotic birds that were being monitored by the New York State Parks Department. Let's just hope that this is a bad omen for the individual and not my new shirt.

Vest: An unlabeled waistcoat I found on a rack at an antique store in Vails Gate, sized for someone twice my circumference. Armed with a Singer sewing machine and naive determination, I spent an entire Sunday tailoring it down while listening to Andhi and the Oneills. Unlike most of my stories, this one is 100% true!

Pants: These Croft & Barrow pleated trousers were picked up in a church thrift shop in Highland Falls. I struck up a conversation with the organizer about the history of the building, which is called the “Church of the Holy Innocents”, named after the children of the architect and Hudson River School Painter, Robert Walter Weir. Turns out his children died young, hence the name “Holy Innocents”. Anyway, these pants are cool.

Boots: You already know by now, my love for Thursday Boots is unmatched. Walking along the Peekskill waterfront has never been easier, thanks to the expert craftsmanship that went into these boots. Yet they also make the most mundane tasks, such as going out to do laundry, feel like I am embarking on a glorious expedition. I can safely say Timberlands have never made me feel that way.

15/06/2025

The Frayed Presenter

Jacket: This Vintage Lee Denim Jacket was found neatly folded at a yard sale off of Route 9D, whose owners were proudly displaying a "No Fjord Trail" sign. When asked why they didn't support the Fjord Trail, they said they didn't want an overflow of tourists in the area. When the conversation progressed to the question of what they did for a living, they said they worked at an antique shop in Cold Spring. Hmm.

Shirt: This IZOD Shirt was given to me by a friend who was clearing out his late father's closet. He reportedly attended every school board meeting for 35 years, long after his kids had graduated, and would pick fights over the introduction of a free lunch program because it was "Communism in its purest form". Not sure what the negative is with that, but in any case, the shirt is made out of silk and fits very nicely on me.

Pants: These Linen-Cotton 90s Loose GAP Trousers were near perfect when I first picked them up in a church basement in Ossining. However, the pockets were too shallow. Naturally, I removed the back pockets and used them to extend the front pockets. The funniest part about this is that this is the only true story I've told in this post.

Shoes: Back at it with the in this fit, I won these in a tense eBay bidding war back in February of last year. They've trudged through Beacon's streets, the questionable trails of Putnam Valley, and once stepped into quicksand in
Jamaica Bay. But thats a story for another day.

Sunglasses: No brand. No case. Just found them sitting on the edge of a stone wall by an unnamed pond north of Peekskill. They’re crooked on my face and filter the world into that soft pink that makes gas stations look like paintings. I’ve worn them to funerals and birthday parties and couldn’t tell you which is which. They’re not prescription, but they help me see things clearly.

Sticker: Speaks for itself (The only important thing in this post).

08/06/2025

The Riverside Naturalist.

Shirt: Once worn by a trust-fund kid who went to Stepinac Catholic School, this Abercrombie and Fitch "Big Shirt" from the 90s is now being appropriated by a man who puts the 'starving' in "starving artist". I picked it up at a church rummage sale where the woman working the table whispered, “That belonged to a boy who turned down Princeton to become a DJ.” Anyways, it's pretty comfy and looks great.

Shorts: These Banana Republic pleated shorts were bought from a retired botanist at an estate sale in Nyack. He said they were standard issue for a 1991 Smithsonian expedition to document flora in the Azores. There's still a faint smell of pressed fern and to***co in the pockets. I wouldn't trade them for the world.

Shoes: I found these Adidas Americana Low Rise sneakers in the dugout of a baseball field in Verplanck. After throwing them in the washing machine, they were as good as new. A more relaxed change of pace from the usual boots I wear.

31/05/2025

The dog; Man’s best friend. Years ago we hunted side by side to provide food for our tribe. These days we continue that tradition by exploring the uncharted corners of our biome. This little guy—affectionately named “Crab Apple Rangoon”—is just happy to be along for the ride, and reminds me to take some time to play and relax, and that the goal of any true adventure is to live in the moment rather than rushing to get to the destination.

Pup: .stacean

Vest: This 80s Banana Republic Quilted Up Vest was acquired from an old photographer for Time Magazine that I met at a cafe in Cold Spring. In exchange for a bottle of Captain Morgan Spiced Rum he gifted me this vest which he claimed to have worn while on an expedition through Albania in the 90s. I then understand why Rum was required to tell those stories…

Shirt: Continuing the Banana Republic habit with this shirt, I picked this up as a thrift item at a New Jersey warehouse. In the front pocket was a movie ticket for a Paris screening of “The Last Temptation of Christ” that read “October 22, 1988”. The ticket was a bit charred…not sure what thats about but the shirt is in great condition.

Pants: You probably expect me to have a story for these Gap Linen 90s style trousers. Nope. Picked them up on sale and they fit pretty well.

Shoes: A loyal customer of thursdayboots I ironically have never purchased a new pair of boots from them. Instead I fought a brutal bidding war to win these for $54.99. I would sell my soul to become a model for Thursday Boots, as these boots are perfect from its style to its durability.

30/05/2025

Albany's Attack on its Black Community...

Sources that helped in the creation of this video:
https://dev.digitalgizmo.com/urban-renewal/stories/albany-displaced.html #
https://www.urbanarchive.org/stories/8THE9YRbFfN

What do you think of this? Let us know!

17/05/2025

I'm a Peekskill Problem. Fortunately for some (and unfortunately for others), I'm not going anywhere. Standing beside the river that flows both ways, I feel tapped into centuries of history that yearns to be heard. What can I do but share what I hear with my community? What makes the Hudson Valley beautiful to me is that it reflects centuries of history and culture, coexisting and thriving. Despite this, it is easy for a resident of the region to take for granted the unparalleled beauty that surrounds us (I am often guilty of this). Yet as the weather gets warmer and we spend more time outdoors, let us all take some time to go off the beaten path and admire this gift that has been bestowed upon us.

Shirt: WXYZ Summer Shirt - Thrifted
Pants: 1940s U.S. Army Trousers - Thrifted
Belt: Unlabled Red/Brown Belt - Thrifted
Shoes:
Pin: "I'm a Peekskill Problem"

16/05/2025

The May issue of the JSB Newsletter is out! Check it out on JonScottBennett.com !

We get into the film of the decade “Sinners”, Thom Johnson’s book series on Bannerman’s Arsenal, some military surplus of my own, and a DIY Eggshell powder cleaner.

And of course, a full list of screenings for the months of May, June, and July where you can see your favorite JSB Films.

Let it shine!

03/05/2025

The trees have turned green seemingly overnight, and I couldn't be more thrilled. Spending some time along the river as the sun is setting over the green Hudson Highlands gives me a new level of appreciation for living in what is-- objectively--the most beautiful part of the country. For today's fit, I wanted to show off one of my new favorite shirts, the 80s-era Banana Republic striped tunic. Made during the "Safari and Travel Company" era of BR, the superb quality of the shirt, combined with its vibrant color, truly helps make any fit stand out. In last month's JSB newsletter (which can be found on JonScottBennett.com ), I discussed my growing interest in this era of Banana Republic, which was in many ways inspired by military surplus (before it became a more expensive and lower quality version of GAP). Also worth noting in this post is the superb work of Thom Johnson on Bannerman's Arsenal, which I used for research in an upcoming short video about the island arsenal on the Hudson. It was a real trip to read some of it over again while looking out over the Bannerman ruins.

Shirt: 80s era striped tunic - Thrifted
Pants: Unlabeled green pleated trousers - Thrifted
Shoes: @thursdayboots

28/04/2025

The One and Only San Antonio 🤠

26/04/2025

Spring is here! And that means that if I wear any more wool I will get heat stroke. Soooo now we pull out the light fabrics such as cotton and linen. Not having heavy clothes is great for climbing on dead trees but I stress that only a professional such as I should be engaging in such activities. This is the perfect fit for the riverside explorer who also has a dinner date at Table 9 later that evening.

Shirt: St. John’s Bay Blue Vintage Shirt - Thrifted
T Shirt: Old Navy Shirt (Dyed Green by previous owner) - Thrifted
Pants: Linen Cotton 90s Loose Trousers
Shoes: Chukka Boots

18/04/2025

The April JSB Newsletter is out! Check your email or go to JonScottBennett.com/jsb-newsletter

We go over our 1000 Subscriber milestone and Q&A video, as well as our shorts videos, and my “Book of the Month”.

Join the email list if you haven’t already!

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