This beanie is not meant to be worn slouched or loose fitted. It fits your head size even if it is small, snug. But not so snug that it hurts your ears even if you are wearing glasses with thick arms. The hat is warm but breathable - it is more for 20 degree temps and higher but dont let that dissuade you. I wore this hat inside a party for like 3.5 hours before i realized i forgot to take it off. That is how comfortable this hat is. No itchiness. No compression on your head. Finally the hat looks classy because of how well it fits, looks way more expensive then what it really costs (would love to see the cost come down slightly due to location of manufacturing), and is by far the best beanie for the 28-90 year old crowd. If you want a street wear beanie this isnt it. I think the best word to define this hat would be, REFINED