Holiday Blues: A How-To Guide For Wearing Men’s Denim This Season

The holidays are undoubtedly the most wonderful time of the year. And although this year’s celebrations might look a little different, you can count on Flag & Anthem to have holiday outfits that fit whatever the happenings. Whether you decide to get dressed up or just want to kick back, relax, and keep things casual, denim is always a great choice, and the men’s denim from Flag & Anthem is no exception. Available in 5 fits, 3 lengths, washes for any and every occasion, plus complete with built-in stretch for max comfort and ease of movement, your perfect pair is possible. As for your perfect holiday outfit? Keep scrolling for some of our favorites.


Christian McCaffrey in the Ames Stretch Flannel Shirt

As comfortable as it is classic, a flannel shirt paired with jeans is an outfit you can always count on. Super-soft, casual, and effortlessly cool, the Ames Stretch Flannel Shirt from Flag & Anthem is made for everyday moments and all-day wear. Crafted from one of our favorite stretch-infused fabrics that is ready to flex and move when you do, this long sleeve flannel shirt wears well with everything and will be your go-to no matter what you have planned.


GET THE LOOK: Ames Stretch Flannel Shirt; Mauldin Crewneck; Roanoke Jean; Edgemont Boot

Now that you’ve found your new favorite flannel shirt, it’s time to finish your look with a pair of comfortable denim jeans. The Roanoke Jean from Flag & Anthem features a dark wash that is endlessly versatile and that can easily be dressed up or down depending on the occasion. Complete your look with brown lace-up boots, good to go! 

Denim Tip: Dark wash denim jeans are a staple in every man’s wardrobe, mainly because of its versatility, durability, and timeliness. Easy to wear with a myriad of outfit combinations, you can dress dark wash denim down with a comfortable tee or dress it up with a sweater or blazer. 



If your holiday plans include binging an array of festive films, you’ll want an outfit that allows for maximum comfort. Keep cozy and warm in a super-soft sweater and a pair of stretch denim jeans.


GET THE LOOK: Lavelle ¼-Zip Pullover; Parmer Stretch Flannel; Vienna Jean

Start your look with a super-soft sweater layered over your go-to plaid shirt for a look that perfectly captures the holiday season but still keeps you feeling as comfortable as ever. And since light wash jeans create a more casual look, the Vienna Jean from Flag & Anthem is the perfect pair to complete this look. 

Denim Tip: Inherently more casual than their darker counterparts, light wash denim jeans convey effortless off-the-job, weekend-ready relaxation. A cornerstone to your laidback wardrobe, light wash denim jeans have a hint of wear in them, even from the first time you pull them on.




It may be the best time of year but it’s also the coldest. Give your holiday looks an extra shot of cool with effortless and easy to wear layers made for crisp conditions. So soft you’ll never want to take it off with a classic design built to keep out the cold, the Newdale Shaggy Sherpa Vest from Flag & Anthem will keep you warm all day long.


GET THE LOOK: Colerain Burnout Fleece Hoodie; Newdale Shaggy Sherpa Vest; Paton Jean; Edgemont Boot

For a memorable holiday outfit, lean on elevated essentials like a super-soft hoodie and jeans with stretch. Classic style with a laidback look and modern feel, this outfit is perfect for rockin’ around the tree. 

Denim Tip: A favorable shade of denim to have at your disposal, medium wash denim jeans have the ability to seamlessly slot a place into any of your favorite outfits. Medium wash denim has also undergone a longer washing process, meaning they’re super-soft to the touch and ultra-comfortable for all-day wear.

We hope these men's holiday outfit ideas give you some inspiration. Want even more tips and tricks on how to put together comfortable and casual outfits that look as good as they feel? Check out our Shop The Look page.