The 27 Times You Should Not Wear Plaid Flannel

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A few weeks ago, I walked into my office only to realize that everyone was wearing a slightly different version of the same shirt. I don’t mean the ubiquitous Oxford, either; we’ve reached that week in fall where everyone reverts to their plaid-patterned lumberjack staples and resigns themselves to sticking with it all winter. It’s flannel season! The most comfortable time of the year! That’s all well and good, but don’t fool yourself into thinking you can get away with wearing flannel and nothing else until March.


In fact, there are times when you can absolutely not wear flannel.

1) When it doesn’t fit right.

2) When it has holes in it.

3) When you’re at a fancy party.

4) When you wore the same shirt yesterday.

5) When you’re working out.

Yes, these rules go for most clothing, but we’re just reiterating here, given that it’s the season where it’s a bit too easy to hibernate inside the same blanket-like clothing for the next four months. Change it up, do some laundry, and at least try to introduce a second favorite flannel into your repertoire, okay? Got it? Good. Also, don’t try to wear these things to places beyond your home/local bar/casual office. In other words, don’t try it when:

6) You’re going to a funeral.

7) You’re going to a wedding.

8) You’re going to a job interview.

9) You work on Wall Street.

10) You’re going to a meeting.

11) You’re leading a meeting.

12) You work as a lifeguard.

13) You’re on a deep-sea fishing trip.

14) You’re participating in any kind of water sports at all.

15) You’re going to the club.

You think any of that is gonna work out for you? Consider Chris Brown, who regularly trots out a “flannel in the club” look, with limited to no success. Unless you’re going out to one of the few bars in America where they still allow smoking indoors, or you’re Beyoncé in the “***Flawless” video, or you’re going for a Dad’s Night Out look, wear something else.

Flannels are great! You may like to wear them with jeans or dress them up with a tie every once in a while, or wear them when you’re out in the yard chopping wood. They’re versatile! But never, ever wear them in the following ways:

16) When you’re wearing plaid pants (unless you’re a golfer, which this gentleman is not).

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17) When it’s dirty, or you are. (Grunge is dead!)

18) When you’re also wearing overalls (unless you’re actually a farmer).

19) When you’re also wearing a bright-orange beanie and head-to-toe Carhartt (unless you’re actually a lumberjack).


20) When you’re also wearing a plaid pocket square.

21) When the shirt is $700.

22) When you’ve been advised by any of the “How to Style Flannel” videos on YouTube:

23) When you’re trying too hard (see above).

24) When it’s a pajama set and you’re not a dad.

25) When it’s a pajama set and it wasn’t a Christmas gift from your mother.

26) When you look like Al Borland:

Image for article titled The 27 Times You Should Not Wear Plaid Flannel

27) When you realize you’re starting to regularly match your couch.

Adequate Man is Deadspin’s new self-improvement blog, dedicated to making you just good enough at everything. Suggestions for future topics are welcome below.


Lead image by Sam Woolley.