Our newest pod is all about menswear rules and advice and how most of it is bullshit, especially once you get into your own personal style.
Listen to the Podcast Episode here!
- People look up to the Ivy-Leaguers of the 1950s and 60s for their style, but ironically they usually weren’t concerned with rules.
- We think not getting caught up on rules is more cool.
- Many menswear rules were invented to keep out new money and have roots in elitism and class-ism (white after labor day).
- There are distinctions between rules, guidelines, and advice. People tend to lump all three together.
- Beginners gravitate towards rules because it’s easier to know what not to do. The more variables, the easier it is to get something wrong.
- If everything else in your outfit is good, it’s easier to break rules, because the rule breaking appears more intentional.
- Sometimes people will dismiss the entire outfit for one thing (pleats, white socks), but we find that ridiculous.
- Some men, like Kamoshita-san can break major rules, like jacket buttoning, and still look great.
- People don’t pay as close attention to your dress as you think.
- Rules hinder people from achieving true personal style.
- You can’t achieve a good look while breaking rules in just anything. For example, you can’t mess around with button rules on an off the rack suit because it will not fit right.
- Before you break the rules, you have to have experience and understand what rules you can break with the wardrobe you have.
- Try to be nonchalant, don’t look like you’re trying to hard.
- Most men use rules not to encourage better dress, but to feel superior.
- Being obsessed with rules takes the fun out of dressing up.
- The cool guys in pop culture have usually been rule breakers. Jeans and t shirts were not everyday wear until James Dean, Marlon Brando, and others wore them in movies
- Fashion will not evolve unless rules are broken
- There are still trends in classic menswear.
- Things change, but slightly.
- People online tend to say that you can only break menswear rules if you’re handsome, but that isn’t true
- In most cases, intentional choices look good.
- Personal taste=/=bad outfits
- For the most part, if you can’t picture how a piece of clothing could potentially look good on someone, it’s because of a lack of creativity on your part.
- A white shirt, jeans, and loafers can be worn good or bad depending on the items and intention.
- Baggy does not mean wide. The “baggy” look is usually because the pants are too long.
- A more casual approach helps helps. We wouldn’t wear a black worsted wool suit with a tee shirt, but we would with a black linen or seersucker suit.
- We all have our own personal rules and guidelines, but they’re just for our own style.
- Ethan doesn’t wear derbies with DB jackets.
- Dress for yourself, not to be superior.

Kamoshita-san.

I don’t even know what I expected.
Recommended
- Handcut Radio with Greg Lellouche
- Talks about dressing for yourself.
- Sprezzatura can seem affected despite being contrarian.
- Handcut Radio with Mark Cho
- Has a quote where he says if you can separate the suit from its formal connotations, you’ll be able to appreciate it more as fashion: “a simple matching pair of jacket and trousers”.
- Reddit thread on PTO’s White Socks article.
- RMRS on Rules You CAN Break
Q & A
(From IG Livestream): Can you shop at H&M and still dress in the styles of classic menswear?
A: You can’t.
It isn’t your fault, but the fault of the manufacturer or brand. You can still look good in H&M (MFA basic bastard look), but you can’t get details like soft shoulders, wide lapels, or long collars. There is a reason why we like vintage ties and jackets; they have details they don’t do anymore! Try thrifting/eBay as it provides a cost-effective avenue to cool details without relying on fast fashion. Or look at places like Spier & Mackay, as they do Neapolitan inspired jacketing.
From @progshell : My sister and fiance all say I look like Spencer. What do I do with this information?
A: Deal with it bozo.
Submit your questions and stories here!
Thanks for listening! We’ll see you in the next one. Buh-bye!
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