
You wanted a full episode on headwear for fall, here you go! To be clear, not every piece listed starts with a “B” – we tried.
I’ve written about hats in menswear countless times over the years and decided that it would be pertinent to have one place for them. It’s currently the end of October at the time of writing and we finally dipped into mid 60s weather…until shooting back up to the 80s as October creeps into November. It may not be the perfect time to talk about hats, especially since we’re not going outside very much, but hey, at least we have it.
I will say that after growing out my hair, I prefer to have my locks flowing loose, but I’m sure that will change as the weather gets cooler (hopefully). It’s also been a while since I’ve visited a few of these topics, as many of them were written almost a year ago! Hopefully you guys will enjoy the episode and get a lot of inspiration from the plethora of pictures below.
You can listen to the episode on all podcasting platforms or by clicking this player below!
Outline
- 3:05 – Intro
- 4:20 – “Is ‘meat the press’ when you throw sausages on journalists?”
- 9:05 – Headwear that Starts with a B: Berets, Bucket Hats and Beanies
- 12:00 – “At its core, headwear is going to be a practical piece. They’re designed to be utilitarian, we might just not need it for that purpose.”
- 17:55 – Beanie
- 19:50 – “It has a skater, workwear and military vibe and makes the outfit very casual. It can be very practical as well, and so easy to throw on.”
- 25:20 – Beret
- 27:00 – “The beret is a more intentional choice than a beanie. Anyone can throw on a beanie, but if you go for a beret, you definitely chose to wear a beret.”
- 29:25 – “If your style leans more tailored, the beret is a better choice over the beanie. Some complain of looking too young with the beanie, but the beret doesn’t have that problem…I prefer it with tailoring because it gives an edge to tailoring.”
- 34:55 – Ball Cap
- 35:10 – “Let’s get brimmed!”
- 37:35 – “It’s practical, sporty, has that Americana feel to it, and you can buy from Ebbets Field – of course you can also buy them more locally.”
- 41:20 – “With logos for dad caps, getting something that’s personal to you, it doesn’t have to be sports- I have no loyalty there.”
- 50:20 – Bucket Hat
- 50:35 – “While the dad cap is the easiest hat to get into, the bucket hat is the easiest to wear.”
- 54:15 – “Bucket hats dress the suit down even further than the other hats, there’s far less branding than with dad caps, it becomes this casual floppy hat.”
- 56:35 – B-Fedora
- 59:10 – “The fedora is most like denim: if you wear it in really well, it becomes softer and that much easier to wear each time.”
Recommended Links:
- Case for the Knit Cap
- A Case for the Bucket Hat
- Pulling off the Menswear Beret
- On the Subject of Fedoras
- Die, Workwear on the Baseball Cap
Stream Discussion on Headwear





















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StyleandDirection | EthanMWong | SpencerDSO
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