How to Wear Flannel Stylishly

November 14th, 2007

How to Wear Flannel, courtesy of the Sartorialist

Flannel is one of those things people seem to avoid because, I think, they are scared of looking like an early 90’s grunge rocker wannabe.  And it’s true: flannel can look very grungy when done sloppily.  It’s too bad, though, really.  Flannel button downs are great for locales with colder fall seasons such as the Northeast because of the heavier fabric.  Plus, the patterns, usually plaid, can make a bold statement.

So if you want to stand out from the crowd, wear flannel–but do it right.  Here’s how:

Find a Great Flannel Shirt:
First off, you need to find a flannel shirt.  Well-made flannel shirts aren’t the floppy and flimsy pieces that you probably saw in the 90’s.  No, they have lines and form a great shoulder.  And while I said they aren’t floppy; I didn’t say they aren’t soft.  Here are three of the best flannel shirts

Oak Slash Pocket Buffalo ShirtPictured: Oak “Slash Pocket Buffalo Plaid Shirt” | $130 at Oak
This is a great piece from a great store, Oak NYC.   The bold pattern goes well with anything, from jeans to a wool coat.  It looks boxy in the picture, but it’s not when you wear.  Notice the absence of a collar; it’s a ring collar, similar to that of a t-shirt.  The pocket detail, Oak’s signature, is another sleek feature. 

Steven Alan “SA Work Shirt” | $178 at Steven Alan
I really like this shirt in Red/Green (use the "choose a style" dropdown to view).  Bold and colorful, it’s slim fitting and has a great shoulder.  It also has a hint of rugged outdoorsman sex appeal.  The picture doesn’t quite do it justice.  Also be sure to check it out in White/Navy.

Cassette Flannel Shirt | $253 at Revolve Clothing
A little pricey, to be sure, but very stylish.  It has a hint of West Coast/Southern California fashion, but it doesn’t obnoxiously scream “Los Angeles” like those Ed Hardy graphic Ts do.  The slightly faded pattern gives it a worn-in (in a good way, like a pair of jeans) vibe. 

 Craft an Outfit around the Flannel Shirt
As always, fit is going to be key here.  If the shirt is big on you, it will look very sloppy.  Too small, and you’ll give off an emo rocker vibe.

Since these patterns are so bold, you want to let it be the focus of your outfit.  Whatever else you wear, make sure it’s subtle and, preferably, patternless.  Wear your flannel shirt with some dark denim with no fade (or a subtle one at the most).  Well-fitted khakis would also work—and they’d look especially good with the Steven Alan shirt.  The tan from the khaki complements the green and red, which immediately stand out, but it’s the subtle brownish base that really makes it work.  If it’s cold enough to wear a jacket, pick one that isn’t too busy and one that picks up or complements the base color of the flannel shirt.  As for shoes, sneakers should (as always) be low tops.  Shoes other than sneakers can also work, but this look is harder to pull off.

How you wear your hair is actually important here too.  Having medium or longer hair will give off kind of an indie rocker vibe.  I’m not saying you shouldn’t wear flannel with longer hair, but I’m not saying you should either.  I think shorter, more styled hair gives it a refreshingly sleek look.

Last tip?  Don’t bother wearing an undershirt with these flannel shirts; wear just that shirt and button it, but not all the way.

Photo of man wearing flannel courtesy of The Sartorialist.

Have a great tip about how to wear flannel?

Share it with us in the comments!

Style question?  We’ve got answers.  E-mail us at tips at omiru dot com, or leave us a comment with your question.

Entry Filed under: How To,Men,Men's

18 Comments Add your own

  • 1. Designer Ella  |  November 14th, 2007 at 4:53 am

    I’m not sure… the picture doesn’t convince me. Need more proof. :-)

  • 2. Trisha  |  November 14th, 2007 at 3:43 pm

    Fair enough :)

    John sent me this photo of a man wearing flannel, courtesy of the Sartorialist.

  • 3. John  |  November 14th, 2007 at 5:49 pm

    I actually agree with you Designer Ella; Oak’s picture isn’t the most flattering.

    The Oak and Steven Alan pieces are worn by mannequins, which I don’t like because the buyers doesn’t get a true sense of the fit.

    I have seen both the Oak and Steven Alan shirts in person, and I assure you, they fit much more like the guy in the Sartorialist’s picture than the ugly boxy fit on the mannequins. They have very defined shoulders like the man in the picture’s shirt, and they are soft but not flimsy and pathetic.

    Just TRUST ME!

  • 4. Trisha  |  November 14th, 2007 at 6:02 pm

    Updated the post with the photo courtesy of The Sartorialist :)

  • 5. Mimi  |  November 14th, 2007 at 8:49 pm

    I once thought I looked “local” (as in, not a tourist) when I donned a flimsy, floppy plaid flannel shirt to wear while strolling around Edinburgh, Scotland. About halfway through the day I realized I looked completely ridiculous! I will forever associate plaid with a deep sense of humiliation.
    I’d much rather wear the animal print blouse.
    Great article though!

  • 6. John  |  November 15th, 2007 at 12:03 am


    The woman wearing the animal print is Anna Dello Russo. Here are some more pictures:

  • 7. Catherine Nelson  |  November 15th, 2007 at 1:19 am

    I love the shirts. Do you guys have any ideas for women?

  • 8. John  |  November 16th, 2007 at 2:43 am

    Ahh Catherine, you’ll have to ask Colleen, but if you happen to like the Oak shirt, they make a dress in the same print. –> one of my favorite stores

  • 9. Trisha  |  November 16th, 2007 at 4:47 am

    Hi Catherine,

    Just added this to our women’s Q&A queue…will get back to you about flannel shirts for women!


  • 10. Catherine  |  November 17th, 2007 at 1:06 am

    I stopped by Gap tonight and saw they have several flannel shirts for men and women in various tartans/plaids. They also had one that reminded me of the Oak shirt – I wonder if they used the Oak shirt/dress as inspiration. Look forward to seeing your other suggestions! The Gap tops had good color, but the lines seemed a little flimsy (at least the women’s). The men’s ones looked better – though I prefer those featured in John’s entry.

  • 11. John  |  November 17th, 2007 at 11:33 pm

    Here’s the Steven Alan shirt in a color that I guess they don’t sell through the Steven Alan store:

    This one is noteworthy because the material is flannel, yet it looks like a dress shirt:

    Finally, here is one that incorporates the same red/green plaid by
    Steven Alan I suggested into a puffy-but-not-obnoxiously-puffy down
    vest. Not surprisingly, the vest is by Steven Alan:

    These three suggestions are all from Jake, a great store in Chicago.

  • 12. Trisha  |  November 20th, 2007 at 2:36 am


    I was at American Eagle over the weekend, and I saw a shirt that reminded me of the Oak plaid shirt.

    It’s not flannel, but it does have a nice tuxedo pleat detail at the front. I ended up getting it :)


  • 13. Rachel  |  November 24th, 2007 at 11:06 pm


  • 14. Style for All&hellip  |  December 4th, 2007 at 2:26 am

    […] December 4th, 2007 The Plaid Flannel Shirt is back–and it doesn’t have to be (nay–it shouldn’t be) reminiscent of 90s grunge. John showed the guys how to stand out from the crowd in a plaid flannel shirt, which prompted the ladies to ask how to translate this look for women. The plaid shirt, while reminiscent of a woodsy man, doesn’t have to be masculine. How to give the plaid shirt a feminine touch? Three ideas:(1) Fit is key. A man’s shirt will fall straight at the sides, but a woman’s shirt should follow her curves. Too-straight side seams will make you look mannish. (2) Leave the top button (or two) unbuttoned. Subtly show off your figure. (3) Choose a shirt with special details, such as a ruffle at the back or tuxedo pleats down the front. The tuxedo pleats down center front on the American Eagle shirt, for example, give the shirt a feminine edge. Here’s our top picks for plaid shirts with a feminine touch: AE Plaid Tuxedo Pleat Shirt | $34.95 (sale) at American Eagle Bib Front Flannel Shirt | $44.50 at Gap Sparkle Plaid Margaret Shirt | $78 at J. Crew Charlotte Ronson Plaid Button Down Tunic | $202 at Shopbop […]

  • 15. brad  |  December 4th, 2007 at 3:16 pm

    I love the plaid look, and just posted a recent purchase of mine from GAP on The berwick plaid pattern looks awesome.

  • 16. Trisha  |  December 7th, 2007 at 1:16 am

    Thanks for sharing, Brad!

  • 17. John  |  December 30th, 2007 at 2:41 am

    i like the jacket on the left:

  • 18. Billy  |  September 6th, 2009 at 2:30 pm

    Is the guy in the picture wearing a chukka?
    I’m looking for shoes like that.

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