SaDCast Show Notes: The Rule of Cool

We’re discussing the “rule of cool” and how it applies to menswear on our latest pod episode!

Listen to the Podcast Episode Here!

It’s a trope!

  • Some things are cool and some things aren’t, but it’s nebulous.
  • We started using the term to refer to which period accurate vintage outfits were cool and which weren’t.
  • Dressing up can be just as cool as dressing down, but sometimes the issue is how the person wears the outfit (demeanor, attitude).
  • If it’s cool, people will like it, if it’s not cool people won’t like it.
  • Be casual with it. Even if you wear a suit, you can look casual. And that’s all entirely on how you present yourself.
  • As Ethan Newton said, we are wearing “old man clothes”. It’s our job to make it look cool!
  • Ethan (the Wong  version) got into contemporary-classic menswear because at a certain point, he didn’t think vintage (or being period accurate) was cool.
  • We tend to not wear shoulder pads, but they can be cool (Edward Sexton, Cifonelli,’70s English rockstars). Once again, it has to do with the attitude of the person wearing it rather than the items themselves.
  • Vintage people and “dapper bros” tend to affect a high society attitude, which is not how many 1930s movie stars would pose in photos.
  • There’s a fine line between caring and not caring, and that line is being cool.
  • Being comfortable in your clothing can go against some rules of menswear, which is what makes it cool.  Rebellion is cool.
  • Don’t be worried about how people perceive you, or at least pretend not to worry.
  • Don’t act like you’re better than everyone else.
  • Being cool takes self awareness, so don’t try to be something you’re not.
  • Wear things because you like them. Be picky and buy things because you know you can pull it off.
  • People take less consideration into what you are wearing and focus instead on how you look in it.
  • With the rule of cool, you can wear a three piece and a beret and blend in more easily than you could a three piece and a fedora.  Because a beret is slouchier than a fedora, though there are cool ways to wear a fedora.
  • When things are cool, things are easy.
  • There’s a difference between thinking about something and overthinking it.
  • Natural shoulders, 3-roll-2, wide legs, etc. are cool (according to us).
  • Having a tie gives you another thing to be careless about, hence why Ethan prefers wearing ties than going tie-less (with a normal dress shirt)
    • If he really wants to dress down, he will wear a sportshirt, which doesn’t hold ties at all.
  • Loafers can sometimes be the “incorrect” choice, but that’s what makes it cool.
  • Cool isn’t just your perception as it also takes other people into slight consideration.  The struggle is finding a way to do both, but in the end, you should definitely be yourself.
  • Take good photos if you’re trying to craft an online presence. Even if you’re outfit is cool, it won’t matter if the photo isn’t.
    • This doesn’t matter if you’re not trying to be an iGent.
  • Clothing can be cool if it has a story or experience behind it.  Hence why Spencer has a list of places to shop.
    • Coolest places to get menswear
      • Bespoke- from a local tailor or a small Italian shop
      • Made to measure
      • Vintage/thrifted
      • Department stores
    • Coolest place to get casual wear:
      • Inherit it
      • Flea markets
      • Curated vintage stores
      • Thrift stores
      • Mall stores
  • Communicating a story through fashion is cool.
  • Try to identify what you think is cool and figure out why! This will help communicate your style and the story you are trying to project.

Strong shoulders are cool. Not everything has to be soft.

Ethan Newton, one of the coolest guys there is.

Jimmy Stewart looking cool.

The ex-Drake’s boys all look cool!

An unkempt tie is cooler than having no tie, according to Ethan.

Good photography is cool!

Bing Crosby in a denim tuxedo.

Casual wear will always be cool.  Applying those principles to tailoring is one way to make a suit look easy!

The slouchy tailoring of Jake Grantham.

Q & A

From Sam:  What are your favorite repro menswear?


From Valtteri: Where can I find the best ivy style inspration?


From “jeremy”:

Submit stories and questions here!


@spencerdso & @ethanmwong | @styleanddirection


  1. Eugene · October 30, 2019

    Cool podcast guys! I think context is key as with all things..
    My opinion is that a “cool” style has something to do with modifying the “uniform” of any existing sub culture with elements of another subculture whilst still maintaining the integrity of the original, at least if the wearer is trying to appeal to a larger group, or authority figure. Usually the sub culture is socially parallel or higher if the wearer is aspiration, otherwise its parallel or down, think Trad to Ivy style with the lack or additional of pleats, slimmer silhouettes in the trousers etc. I think these intentions are what leads to Up-Down dressing.The limits vary depending on the setting, but sometimes even the intention is rewarded by the less sartorially inclined (i.e normal people who don’t spend too much time musing on fashion in the comments section..) if the attitude is right.


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