A few years back I received a flannel shirt as a Christmas present. While I wasn’t familiar with the brand, the shirt quickly became a staple in my wardrobe. It was one of those pieces that stood out from the other shirts in my closet at the time, not because of the color or pattern but because of the quality and construction. As the years passed, a majority of my other shirts slowly migrated into the donation box or recycling bin due to poor material and overwhelming signs of wear. But this particular shirt stood the test of time and is still in my closet (or on me) to this day. 

As I’ve grown older, my fashion tastes have shifted. I find myself shying away from the temptations of fast fashion, and am actively seeking brands that focus on not only quality, but those that create pieces that are more of an investment with timeless collections that will last wear after wear and year after year.  

So after a recent clean out of my closet in preparation for the colder months, I took a look at the growing pile of clothing that didn’t make the cut. My eyes then shifted to the shirt that once again renewed its worthy place in my closet. I needed more clothing like that shirt, and I took a closer look to find out what company had made it. That brand was Jeremiah 

Jeremiah has been around since 2007. It’s a brand that takes classic men’s staples (henleys, flannels, outerwear), and bumps up the typical quality you might see with other brands, and adds the perfect amount of modern day design that keeps your style current yet timeless. For me, it doesn’t get any better.  

Recently I went on a weekend winetasting getaway to Walla Walla (a hidden gem of a town in Washington State), and it was the perfect opportunity to try out some of Jeremiah’s latest designs and explore some pretty amazing wineries in the process. Here are my top Jeremiah picks from their fall/winter collection and why I selected them, along with a few wine-tasting highlights: 

Heath Flannel  


There are flannels, then there are FLANNELS. This shirt is what most flannel shirts dream of becoming. A very structured, yet comfy blend of poly wool brushed twill with double flap hidden snap pockets. The yarn dyed plaid colors blend to perfection, enough to make a statement without being overwhelming. This is the perfect versatile piece to wear as a shirt or open up the front for more of a shirt jacket style. $118

Wine Pick: The Charles Smith tasting room is located in the heart of downtown Walla Walla, with exposed brick and a modern industrial vibe. Try the 2014 Boom BoomSyrah, where savory herbs meet berries for a complex and rich taste.

Otis Quilted Bomber Jacket 

If it didn’t get down to sub zero temperatures here in Washington State during peak winter, I’d live in this jacket. It’s just that comfy … ridiculously lightweight (maybe more like no weight). While on its own and from a distance, it looks like a classic quilted black jacket, up close you can see the magic the designers at Jeremiah created as the quilted stitching is done in a golden brown thread that adds a little pop. While it is very light, it comes with some great features you’d expect in a heavier jacket with side zipped pockets and a row of awesome (and convenient) pockets inside the jacket around the bottom front. $150 

Wine Pick: Waterbrook Winery’s tasting room and grounds are as impressive as their wine selection. The 2016 Icon Viognier has an aroma of wet stone and jasmine, finished with tastes of peach and white pepper. 

Penn Henley 

If you are looking for pieces to step up your wardrobe, henleys are a great start. They are a must-have basic layer under your favorite jacket, or perfect with jeans for a casual vibe. The Penn Henley is a perfect alternative for t-shirt wearing guys in the winter. It’s not paper thin and the fabric has a chambray stripe, giving it a stand-out style on its own. While it’s available in four other colors, I opted for the oxblood for a little punch. $88 

Wine Pick: Located in the historic Frenchtown school building, L’Ecole N 41 is a third generation family-owned winery. Their Estate Merlot is an elegant blend of clove, cedar and dark fruit.  

Porter Wool Vest 

Vests are often overlooked by guys when shopping for clothing, probably because jackets and coats seem like a more practical purchase. This should be the complete opposite, as vests, especially a thick structured one like the Porter, add the ultimate polished look to any outfit. They show that you aren’t just throwing on any old coat; you are making a decision to look dapper and have thought out your outfit from start to finish. The Porter Vest pays homage to traditional wool waistcoats and heritage hunting vests, and is the perfect versatile piece to wear over a plaid flannel or a simple t-shirt, and its exceptional details and design is guaranteed to generate compliments. $175 

Wine Pick: Amavi Cellars’s modern architectural tasting room has the perfect view of the region, and the perfect place to catch the sunset with a glass of wine in hand. Go for the 2016 Semillon, a refreshing taste of fuji apple and melon with a scent of lemongrass and honeysuckle.  

Just like a fine wine, Jeremiah seems to get better with age. Find out for yourself by visiting Jeremiah Clothing and use code ONNEUPPED for 30% off the purchase of any of the above mentioned items, good until midnight January 8, 2018. Cheers!

(Editor’s Note: Thank you to Jeremiah for sponsoring this editorial feature.)