Flannel Season

Applied Male Fashion

Flannels are a timeless piece that boast a significant cultural mark on the US.  A classic red and black or green and blue pattern invokes the spirit of Fall.  When it comes to selecting a go-to cool weather top tier style, there is little that can beat out, in terms of versatility and season-appropriate casual, than the flannel.

Flannels fall into the category of ‘decision fatigue minimization’ due to the ability to wear them anywhere south of business casual, which is useful when the vibe of the morning is “I want to put as little effort into my wardrobe as possible right now but not look like a complete degenerate”.  When it comes to pulling the look off correctly there is a fortunate amount of wiggle room.  While anyone fashion blind enough can screw anything up, the flannel is dead simple to get right.  Simply grab your jeans of choice and respectively paired shoes and you’re ready to crush everything from dead leaves to spreadsheets.

While the look may be timeless on paper, we understand the hesitancy of some.  There was an unfortunate hijacking by bearded urban IPA merchants who decided that there was something about looking like a 19th century Maine logger that perfectly complemented their personality.  My intuition says that, along with whiskey, beer, axe throwing etc. a fair portion of this crowd tend to adopt habits they consider “manly”.  Whether it’s a carefully adopted façade or internal drive to equalize their otherwise gutter tier hormone labs, we don’t know.

Regardless of this appropriation, you should not be discouraged from adopting the flannel as a fall staple as it’s an excellent way to project a seasonal vibe while maintaining the well put together air of a button up.  It’s perfect for everything between being a 50-degree day drinking degen to taking your kids for a walk through the golden forest. 

What Makes a Good Flannel?

A flannel shirt is simply any collared button up shirt, made of wool or cotton, that sports a checkered or plaid pattern.  Though traditional flannel shirts are made from natural materials, they can just as easily be polyester or any type of blend a fashion house deems worthy to manufacture.  The key element of flannel itself is its looser weave and brushed finish, which yields a softer feel.  This makes it ideal for cooler days when you need something especially comfy to regulate your body temperature as you destroy your whoop recovery scores with hot toddys. 

The unique and somewhat convenient aspect of a flannel shirt is that it’s difficult to mess up when purchasing.  Outside haute couture there is little in the way of designer or upscale flannels that make one distinctly better than another.  There is no Mizzen & Main dress shirt to an off the rack Tommy Hilfiger from Kohl’s comparison; for all intents and purposes a flannel is a flannel is a flannel.

This makes the flannel slot in your wardrobe easier to fill with something that fits your budget.  There are dozens of brands that offer the style anywhere from $30 to $500, and something comfortable that doesn’t feel like wearing burlap can be had easily under $100.  For this purpose, we won’t be recommending any specific brand and rather suggest you take your search to Amazon or your local department store to find something right for you.  You can even thrift some ridiculously hard flannels by trying your luck at the local Goodwill.  This is one of the minority of occasions we recommend doing this.

Color Selection

Flannels come in all different styles and colors, but for the sake of brevity we will focus on the best options.

Red – Obviously the most popular as your average artistic lumberjack will be stylized as wearing the traditional red and black checkered flannel while swinging his axe in the great eastern log mines.  Red deserves its popularity not just from its history but also ability to be most dynamically styled.  Most outerwear pairings will match without effort, as will pants and shoes.  The red flannel looks money with everything from black jeans to chinos. 

Green – The most yee-haw of flannel colors clocks in as green, which can make you look equal parts Denver weed store manager and hay slinging cowboy simultaneously.  As an earth tone, green commands a more ‘naturalistic’ look to red’s ‘metro’ with regards to modern style.  Regardless, some quality boots and a clean pair of jeans will make this look a winner.  As with most earth tones, it’s best to maintain the earth theme throughout the outfit i.e. avoiding any pastel or otherwise saturated colors in the shoes, undershirt etc.

Black – A changeup from the colorful options, black is a sharp that leans significantly more metropolitan.  If a grungier yet modern casual look is what you’re after, then black will the prime choice.  You could even get away with wearing this to a city bar or club if paired correctly.  Note that these can be a bit harder to find, but if you stumble across one for a decent price we recommend copping.

Waist Down Pairings

Now is an opportunity to make your newly purchased leather boots shine.  Flannels and leathers go together like SBF and the liquidate button.

Blue jeans are your friend, specifically dark blue.  These are most effectively paired with the king of leather colors; walnut brown, though most options along the brown gradient will work.  Note; if wearing red then we advise against oxblood and other harder red hues.

Depending on your style of choice, different leathers will accentuate your look in slight ways.  A pair of dress boots is an all around smart style.  Timberlands are more rugged.  Modern techwear dress shoes (looking at you Cole Haan) unironically make you look super ready for brunch.  Your shoe choice should be contingent on your destination.

Top choices for blue jeans will be:

-         Leather dress boots (leather or lug sole)

-         Mill boots (stick to Allen Edmonds or Red Wing)

-         Timberlands (advise going authentic, knockoff timbs can and will look atrocious)

-         Wild Card - Cole Haan Zerogrands (warning, this is 2022-2023 season specific and may not hold up long term)

While blue jeans may be the overlord of options for flannel shoe pairings, black jeans are the dress down jokers. 

It should be noted that with black denim, you will likely be restricted to black or otherwise dark leathers.  We do not recommend dress boots in straight black outside of Chelseas; though a dark brown or washed-out color (think dark grey or earth brown) tend to work.  Still, white sneakers or canvas shoes will be best, and better accommodate the dressed down nature of the black denim. 

The look may run dangerously close to hipster chic but can be easily offset by even a slight amount of size in the chest and arms.  Many such cases of the muscle modifier turning otherwise deep Brooklyn-tier looks into viable fits.

Best black jean with flannel pairings will be:

-         All black or all white Chuck Taylors (bonus points if you lift in them)

-         Classic Low tops (Think Stan Smiths, though we currently like the Roger Advantage by ON)

-         Black Chelsea boots

-         Wild Card – Thursday Boots Captain Boot in Tobacco brown with lug sole (these are a timeless look, work with many other outfits, and the color/styling welcomes natural wear and tear)

Keep in mind of the recommendations for black jeans are not out of the question when wearing blues, though sneakers can have some difficultly pairing properly with blue jeans.  Leathers will be a 100% safe bet and you don’t run the risk of looking like mom picked out your clothes for the day.