The 7 Outfits I’m Living in This Fall

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I’ve been a fan-guy of Huckberry for years. Their approach in delivering inspiration, tips and tricks, and gear is unrivaled. Having had the opportunity to know a number of members of the Huckberry squad personally through my own professional career, I’m lucky to call these guys true friends. You’ll typically find me in at least one piece from Huckberry and today I’m sharing a few of my latest fall apparel finds.

Outfit 1 (Above Image):  “We’re going out to dinner?!? At a restaurant?!?”

After spending a majority of the last eighteen months at home, I’m ready to go out into public, with a collar and a jacket on. The Soft-Washed Oxford from Flint and Tinder coupled with the versatility of the Pack Blazer (also Flint and Tinder) garnered a great reaction from my toughest critic, Kate. The jeans are a light wash Organic Stretch Denim from Wellen and, given the fact that I work within the footwear industry myself, all footwear are from my own personal collection—these are penny loafers from the fine Maine folks at Rancourt.


The 7 Outfits I’m Living in This Fall | Wit & Delight
Outfit #2

Outfit 2: “Ahhhhhhh autumn”

I love jackets. I’ve got an embarrassing collection of them I’ve built through the years. I’ve got parkas, peacoats, bombers, puffers, chore coats … you name it. This jacket is called a Quilted Tanker from Relwen and it’s sleek, warm, and water-resistant. Perfect for layering, this works well over a crew neck sweatshirt, hoodie, or anything else. The kicker: The lining is a vintage camo print which gives me instant credit with my dad and grandpa. The oxford is, again, the

Soft-Washed Oxford from Flint and Tinder (I might own four of these). The pants are the Flint and Tinder 365 Pant which I’ve featured before and have recommended since acquiring my first pair. They’re a fantastic material that stretches and also have a nice refined cut to showcase THOSE BOOTS, which are from my dear friends at Red Wing Heritage—this is their take on the classic Chelsea and it’s not to be missed.


The 7 Outfits I’m Living in This Fall | Wit & Delight
Outfit #3

Outfit 3:  “Saturday in the park”

The “lumbersexual” movement was widely adopted and loved in my home state of Minnesota (when Kate and I met I looked like I should’ve been carrying an ax) and flannel is a staple around these parts of the country. This Flint and Tinder Jackson Flannel is immaculately cut and the perfect weight. If you’re not into looking like you may have just walked out of a lumber yard because, be honest, you’re in finance and sit at a computer all day, go for the following: a simple white crew neck t-shirt underneath, a pair of 365 pants, and, even though you may be tempted to throw on a pair of boots, a pair of classic adidas sambas to lighten the look and give a super casual vibe.


The 7 Outfits I’m Living in This Fall | Wit & Delight
Outfit #4

Outfit 4:  “Running … errands”

I love a good relaxed, comfortable fit. These new Flint and Tinder 365 Joggers take everything I know and love about the traditional pants and add in a drawstring and elastic on the back of the ankle hems. For me, this allows me to wear something other than (gasp) sweatpants with sneakers. The crew neck Dover Sweatshirt from Billy Reid is an instant classic with distressed leather elbow patches which are a cool, durable touch—and it’s made in Canada, so what’s not to like? The shoes are, again, my own, Nike x Stussy Huaraches.


Outfit #5

Outfit 5: “Sweater weather”

This classic Wellen Seawool Fisherman Sweater appears as if you may have borrowed it from your grandpa, which is why I love it. Unlike many sweaters I’ve worn, this is soft to the touch and feels great in addition to being made from recycled plastic bottles and oyster shells. The pants are, again, the 365 Pant from Flint and Tinder, and the shoes are the Classic Oxford from Red Wing Heritage. While I didn’t do this in the photo, bonus points if you roll those pants up a few times and show off some chunky wool socks.


Outfit #6

Outfit 6: “Soccer dad”

During the months of September and October I’ll wake up, check the weather, and exclaim, “It’s shorts and sweatshirt weather!” Kate and the kids think I’ve lost it, but that’s fine with me. The Rhythm Classic Fleece Crew sweatshirt is soft—softer than any sweatshirt I’ve ever worn. It’s like a well-fitted blanket with sleeves. *Bonus*: it’s got hoodie-style pockets in the front without a hood on the back (mind blown). The shorts are also incredibly soft—a nice, simple French Terry Sweat Shorts from Flint and Tinder. Their excellent length (~2-3 inches above my kneecap) gives me the opportunity to jump in and illustrate to my son that I did in fact NOT grow up playing soccer and, at the age of five, he can likely dribble circles around me. I completed the look with nice wool socks and some vintage Nike Dunks that I bought in 2005.


Outfit #7

Outfit 7: “Go take a hike”

The Flint and Tinder 10-Year Pullover has been a staple for me since I got it. It’s a perfect shade of heather grey (there are MANY versions out there, folks) and is perfectly cut for me. I’ve got the Wellen Quilted Sweatpants which are an elevated adaptation of a traditional sweatpant with a nice quilted pattern that allows you to dress them up or, in this case, down for a hike. The boots are near and dear to my heart as I helped develop them. They’re the Vasque Sunsetter—a modern version of our classic sundowner with great cushion underfoot and a classic upper.


Editor’s Note: This post was sponsored by Huckberry. The compensation we receive in exchange for placement on Wit & Delight is used to purchase props, hire a photographer, write/edit the blog post, and support the larger team behind Wit & Delight.

While compensation was received in exchange for coverage, all thoughts and opinions are always my own. Sponsored posts like these allow us to continue to develop dynamic unsponsored content. Thank you for supporting our partners!

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