I'll throw this out there: My biggest dressing challenge isn't transitional weather. You know, that time in fall and spring when it's cool but not cold, almost warm but never hot. (Actually, I don't know. I've never experienced it, but I've read about it a lot.)
My problem is transitional hours. Today, for example:
6 AM: 39F
11 AM: 61F
4 PM: 71F
(and least 75 in the sunroom where I work, with windows and door open)
How DO you dress for this?? I used to think it was just the bad luck of my working hours. Walking in from the car in the pre-dawn cold, leaving in the warmest hour with my coat over my arm. But it's almost as awkward at home.
My outfit from today: sweater dress, sweater tights, sweater boots, long hoodie, hair down. By 3 PM I had taken off everything but the dress, pushed its sleeves up, and bunned my hair; and I almost turned on the ceiling fan. But by 5:30 my toes were icy and I piled the layers back on. I've still got the door open and my hand is getting cold.
I'm just whining. It was a gorgeous day, but the temperature change is so extreme I can't just "set" my outfit for the day and not think about it again. I prefer that, and it works in either hot or cold weather. But today I had to keep thinking: Is it really getting hotter? Will I regret taking off the hoodie? Without the tights how soon will my toes get cold? Am I really starting to sweat in this dress? Should I turn the fan on? Is it really getting cold before the sun is down?
At least the HVAC didn't turn on both heat and cold today!