One thing that I constantly struggle with is what I term "outfit escalation"--when the choice to wear one dressy piece forces you to wear other dressy pieces, because they're the only things that go well with the first piece. And then the overall effect becomes much dressier than intended. This seems to happen to me all the time, and I'm finding myself be the most dressed person in my building on these days, in a sort of formal job interview/presentation sort of way for my particular work environment (fairly casual, though not software company casual).

For example, I've been struggling to style these Banana Republic trousers in a more casual. They have prominent belt loops, so then I need to wear a belt, and tuck in a shirt. And then they're long on me, so I have to wear heels. I'm not feeling pullovers these days, so I reach for a blazer and then I end up looking super formal for my environment. And then I get constantly asked whether I have interviews or important meetings.

Long-sleeved shirts and blouses always end up doing this to me because women's sweaters don't tend to play well with them, so on goes the blazer. Blazers are also nice because they can be taken off and put on easily, in contrast to pullovers.

Unlike a lot of people here, this is why I prefer summer/warm-weather dressing--I think it's a lot easier to be casual, or dress-down something dressier. Pair sneakers with a dress, or wear a linen cardigan with a short sleeved blouse and pants. Or a denim jacket...I guess there is the moto jacket option for winter but I prefer blazers for mobility.

Suggestions on how to dress down flared pants in the winter time? I do wear skinny pants with boots, but sometimes I feel like they are *too* casual for my work environment though I get away with them. And do you experience "outfit escalation" generally? I like tailored/sharp pieces, and feel comfortable wearing them, I just wish they weren't perceived as so formal.