You will never be able to escape your partner’s desire to go to the pumpkin patch—or apple picking. It is a time-honored tradition to celebrate the arrival of the fall season by selecting the best pumpkin that will sit on your porch to greet trick-or-treaters, hop on a wagon for a hayride, and our personal favorite, indulge in as many apple cider donuts as we possibly can. 

You need to keep things as comfortable as possible because you will be moving and expanding (no judgment from us on the amount of donuts you consume). The long-sleeve Heritage Biker Graphic Tee is simple and attractive but soft enough to keep you moving. Pair it with a pair of our lived-in Athletic Jeans in Highpoint, and you will be ready for a full day of fall fun. Since you may be somewhere the wind can pick up without warning, don’t forget to grab the Thunderhead Fashion Denim Trucker Jacket. This is a favorite year in and year out, and you will immediately find out why, when you slide it on, it feels like you have had it for years. Last but not least, we can’t spend all day at a pumpkin patch without sun protection, so we chose the 7-panel Adjustable Born & Bred cap.

Thanksgiving is the middle child of the holiday season. Everyone gets excited about Halloween because it is the first one. It signals change is coming. And it is a little scary. Christmas is the fun one. The one who is everyone’s favorite. Showered with gifts and the one everyone prepares for. Thanksgiving is the one between those which few people give proper attention. And it is the one that makes you fat. We refuse to treat Thanksgiving as a middle child and will instead live it up every year. 

This year, for Thanksgiving, we are going with a color-appropriate look with our beautiful Waffle Henley in Walnut. Not only is it buttery soft, but it is easy to care for just in case you make a mistake while stuffing your face. For the pants, we indulged in the return of corduroy as a fall favorite with our Stretch Corduroy Pant in a Dark Roast. With a little bit of stretch and the ability to retain its shape, these are the perfect pants for Thanksgiving dinner. For the talking point of our Thanksgiving look, we added the CPO Jacket in Cocoa Plaid. Not only is this one of our biggest hits this year, but adding this to the ensemble will make everyone think of pumpkin pie when you walk into the room. You never know; it may cause a psychological effect where people just keep putting pumpkin pie in front of you. All we can say is you’re welcome.

One of the most iconic traditions of the year is Black Friday. Love it for the prices or hate it for the crowds, every family has a tradition that kicks off the holiday shopping season. Whether you are going to jump on the discounted PS5s, snag yourself a new iPhone, or just go along with family or friends, the goal of the perfect Black Friday outfit is comfort while you walk around for hours on end and warmth because you are likely starting early in the morning, if not the night before.

The way we start a look that needs comfort will often begin with one of our unbelievably soft henleys. The Waffle Henley in Dark Roast is always a good base for a look and paired with the Our Carpenter Pant in Camo, it is a look that keeps you feeling comfortable and stylish. The extra pockets and stretch features of the Carpenter Pant will come in handy as you run out of hands with all the great deals you’re getting. Don’t forget to finish the look with the Carroway Denim Trucker Jacket and our new Spruce 6-Panel Wool Varsity Cap. If you want to throw it back to your varsity days, pop the jacket collar for a stylish detail.

Another unavoidable moment in the holiday season is when your boss tells you the date of the office holiday party. Even if you love your job, many of us consider whether we want to spend our off-time with the people we spend 40+ hours a week with. Most of us go. Free booze, a relaxed environment, and a chance to see our more uptight coworkers let their hair down are absolutely worth it. 

Dressing for the occasion often needs to feel like a good mix of office-appropriate (you will be there with your boss, after all) and your off-time vibe. We struck that balance by utilizing our Black on Black Feeder Stripe Polo. It is comfortable enough for the day off and elevated enough for the office. Pairing it with the Relaxed Straight Jean in Cornelius gives us a stellar blackout look perfect for after 6 pm. Of course, we’re never done with styling, so we kept the dark look going with our Western Shirt in Marion. The faded black contrasts us, while the 5-panel Black Bulldog Cap finishes the entire look nicely, especially if you’re not allowed to wear a hat at the office. 

Now, we can get into the holiday parties you WANT to attend every year. Those moments you look forward to for 365 days when you get around your closest circles to celebrate the season. Your personal holiday parties are laid back, relaxed, and all about comfort and fun. Whether you are headed to an event space (clearly, you have a lot of friends) or staying close to the house, this is the time of the year to sit in your comfort.

All of the best comfortable outfits start with a great tee, and a great tee is what we have with the Service & Parts Graphic T-Shirt. The blue and the gray play perfectly into the rest of the look, which consists of the Charcoal Gray Chino (the elevated upgrade your pant wardrobe needs) and the unwavering eye-catching CPO Jacket in Night Sky. When you think of color matching your outfit, this is the standard we go by. Finish the look off with the Denim Trucker Hat.

Christmas Eve signals the end of the road for much of the Christmas season. There is no more shopping, the parties are all finished, and you will almost be guaranteed to be free of Mariah Carey for another year. Spending time with family on Christmas Eve means lots of people are in a small space, warm temperatures are in the house, and the snow falls outside the house. How do you navigate that dynamic? With the subtle art of layering.

We utilized layering here with the classic base layer of a henley. Our LS Burnout Henley has a subtle double-button opening, making it the perfect shirt to layer underneath a button-up. Adding the mid-layer of the Crowders Workwear Shirt utilizes the look well with a classic denim look. Followed by a top layer, the Walnut CPO Jacket is the perfect way to survive the cold outside the home and adjust to the warmth inside. Stay neutral on the bottom with the Relaxed Straight in Graybeard, a look your denim collection is lost without. 

Here it is, Christmas, the day you have been waiting for all year. Everything you have done to prepare all fall and the last few weeks of winter is about to pay off in a blowout party in the perfect closeout of a season. Sure, New Year's is next week, but that is the kick-off of next year. This is the finale of the 2024 season. Christmas is a long day of joy, food, football, and gifts. That means something light, comfortable, and fun is on the docket. Something with a little bit of personality is always appreciated. 

We start our personality with another LS Burnout Henley, this time in Spruce. There is just something about wearing green on Christmas morning. It could be us being festive; perhaps the perfect combination of nostalgia and stellar marketing makes red and green the colors to wear. We livened this henley by making it the outer layer and layering it over the Military Chambray Shirt. The color under the henley gives the two-button shirt the feel of a sweater and elevates it perfectly. Finally, we top the outfit off with the Maneuver Pant in Stone. The light color keeps up light and fun all day, and as the most comfortable and mobile pants in our collection, you won’t mind spending hours on the floor putting together the kids’ gifts.