Reddit mentions of 180s Fleece Behind-the-Head Earmuffs Black

I wear 180s earmuffs like these:

http://www.amazon.com/gp/aw/d/B006U1EM66/ref=mp_s_a_1_1?qid=1450057232&sr=1-1&pi=AC_SX118_SY170_QL70

Haven't worn a hat in years. Highly recommend.

i wear these on my walk to work in the morning. you can judge for yourself if they are doofy or not

http://smile.amazon.com/Degrees-180S-Black-Fleece-Warmers/dp/B006U1EM66/ref=sr_1_1?ie=UTF8&qid=1453327864&sr=8-1&keywords=180s

No good way for someone else to be able to answer this, because everyone is different, and everyone's personal gear/cargo load/bike set up will vary.
My suggestion would be take some practice runs in the clothes you intent to wear(and with the new tires should you get them), and get a feel how much the heavier more restricting clothing, etc, effect you.

Best "estimate" I can give you to go on is to say that for me personally with heaviest clothes I wear during winter riding, and with my rough condition tires on, etc, that my average speed goes down by 3 - 5 mph, and I stop to rest about twice as much.

But, again, that's total winter riding, freezing temps set up. If it's less harsh and you can get away with being less bundled, then it won't have nearly as much affect on you.

OH, another note though. Gloves man. Make sure to have some decent gloves because cold weather riding is harshest on your extremities. I've never cared for "mitten" style gloves, but last year my sister got me a pair of half-finger glove/mittens like these, that to my surprise have turned out to be perfect for my riding needs.
And for your ears, this type of ear-muff-thing is perfect for using with a helmet

Its legitimate for someone to decide they don't want to wear a helmet while skiing (except I think for under 18 in NJ). However I'm going to judge them on their decision. If they were my friend I would encourage them to wear one for everything but backcountry low angle snowfields :). It's too easy to have a collision with another skiier or to find variable conditions in bounds. If you were my friend here is what I would tell you about your list

1. Helmets are not very uncomfortable. Your helmet was very uncomfortable for your head. I'm sure I could find a hat that would be uncomfortable for you too. Here are a few ideas: wear a helmet without earflaps AND a hat. Wear a helmet without earflaps and separate ear muffs like http://www.amazon.com/Degrees-180S-Black-Fleece-Warmers/dp/B006U1EM66 Or just try on a few different helmets before you buy one.
   
   
2. Stop taking your goggles off your face. Never take your goggles off your face and leave them on top of your head. If you don't breathe on them and don't sit them on your forehead they won't ever fog up.
   
   
3. That's pretty annoying. You should probably buy or make a helmet sack. You can start with one of those drawstring backpacks you get for free every once in a while.

Rule 1 my man

http://www.reactiongifs.com/wp-content/uploads/2013/05/angst.gif

If sound is of no concern, these look comfy

http://www.amazon.com/Degrees-180S-Black-Fleece-Warmers/dp/B006U1EM66/ref=sr_1_1?ie=UTF8&qid=1422145362&sr=8-1&keywords=ear+muffs