Essential winter clothing?

I'm a buff guy

As in, a buff doubled over covers the ears and most of my head. I have a small head though.

We know. 😙

My ideal winter headgear would be a windproof headband with a peak. Forehead and ears get bastard cold when it gets below zero, peak keeps sun/wind/rain out the eyes and at night it shields your eyes from oncoming headlamp glare. Majority of my head always gets too hot under almost any cap.

Winter golfers know...

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I guess cycling is the new golf...

Both the DHB aeron lab all winter bib tights, and the gore c7 full windstop bib tights didn't fit me properly - so i'm going to try and return them and go for some thermal bib shorts and good quality thermal leg warmers/over tights.

I use these with a "normal" cycling cap. Looks ridiculous but works well

I do this, with a castelli peak-less cap thing

I work as a courier, I have to ask customers to repeat names etc enough as it is without making my hearing any worse with those. Thanks for the suggestion though!

IME they don't damper any sound but I get your point

For commuting I stick to a Sealskinz and shorts combo all the way through winter.
I have been rocking these waterproof Madison Roadrace 3/4 shorts for a few weeks and really rate them.

They are comfy enough (in cold weather at least) that I am happy to wear them in dry weather just as much as wet weather. They're stretchy and breathable enough to make for a decent wind breaker layer.
Waterproofing is good, but not absolute. If you get the kind of rain that is annotated with three droplets in the BBC weather forecast they would last about 20 min before letting moisture through. For anything less than that I would expect them to hold out for up to a couple of hours.

No reinforcements in the bum/crotch area so longevity might be an issue.

I'm looking at getting some Sealskinz socks - how do they size? Obviously I don't want them too tight, but I imagine it's as much of an issue if they fill the shoe too much and bunch up?

https://www.ebay.co.uk/itm/Madison-Isoler-Merino-Winter-Cycling-Cycle-Hat-Cap/302583474367

Unpadded, non-bib tights?
My DHB ones have done a few years of commuting and training and are quite holey now.

howies ones are my go to tights

I also have some bioracer ones for worserer weather

howies ones are my go to tights

Where do you get 'em from? Howies direct?

Yep. All sold out. They had a sale recently, must have sold them all. Sorry! I think they were £35 or so

https://howies.co.uk/products/mens-unpadded-bib-tights?_pos=3&_sid=0e2c0e2cd&_ss=r?variant=19182698102851

They're also bibs. I want non-bib.

Gilet with a mesh/breathable material back. Does it exist?

The Rapha Pro team lightweight gilet does. Also on sale currently :)

Decathlon RC500 Van Rysal. Mesh back and pockets. £19.99

Not sure if winter appropriate but I have an older one of these which is fine against the wind

https://voidcycling.com/void-wind-vest-phantom-black.html

or
https://www.rapha.cc/gb/en/shop/pro-team-lightweight-gilet/product/PLW03XXNYE

Of course. I've still got one from Oz that I get to use for about 3 days a year in the UK.