Sometimes my husband and I go for an hour ride...alone if we're lucky! But often our youngest son wants to know where we're headed. If it sounds interesting, he'll tag along, but in this cooler fall weather we insist he dresses well (my husband will throw extra items in his panniers). I like our boy's choice of fleece-lined sweatshirt and hand-knitted mittens. The hood is enough head coverage. Often the mitts or socks are mismatched, which makes him all the more endearing.
My husband takes a different approach, requiring only bike gloves when the temps hover in the 40s. He is also very colorful and coordinated with bright yellow helmet, coat, and fenders. I bought him this rain jacket years ago when he was commuting during the darker months. He refuses to use a reflective vest or mirror, so I'm happy he took a shine to this coat.
That green bandanna you see dangling from his handlebars...he ties around his ears - when he needs it. The hub's never been the height of fashion; frugal would be an apt description (who better to offset my, ahem, cafe addiction?).
As for me, I'm more traditional in my clothing. I prefer a fleece headband under my helmet as it's less constricting than a hat or hood. I love tights, especially Under Armour's cold weather-weight style. The only cycling specific clothing I own are stiff soled shoes and sandals, but they're in the closet waiting for spring. Currently I'm clad in lightweight hiking shoes with thick wool socks. I gravitate toward multi-use items that can double for walks in the woods and cross country skiing.
I use fleece gloves, sometimes one pair inside another. I'm always snuggled in a fleece coat (around the house too) with a nylon coat for added warmth and wind protection. Colorful skirt, not required!
With the right outerwear I can extend my riding season. As you can see, there's a broad spectrum of comfort levels when it comes to cycling in the cooler months.