I put away all my true summer clothes in October, but some of the clothes I kept out for the fall/transitional season, I'm discovering, have a lower-than-expected joy factor. These are things I look at and love, but once I put them on I just feel "off" somehow.
In particular, I am not reaching for my striped tees, even the long sleeve ones, which in theory are a nice cut/weight for layering under a blazer, hoodie, or cardigan. I guess nautical stripes are too breezy and summery to wear this time of year. This is probably why I've never been drawn to the heavier-weight breton tops like the ones from Saint James -- I really only need warm-weather bretons!
Other items that feel too "breezy" this time of year: chinos and light-wash denim. In theory these are great transitional items, but in practice I'm tired of them by October, even if it's warm and sunny out. I haven't reached for these at all in November, except under extreme laundry-induced duress.
What I want to be wearing instead: plaid instead of stripes. I definitely need to add a couple more flannel shirts to the rotation, in different lengths and weights. Possibly pinstripes: if I'm not wearing striped tops all the time, striped and plaid bottoms become a workable option. Corduroy and black/grey denim instead of lightweight slouchy chinos. Thick cozy sweater tunics, hooded dresses, etc. are interesting to me again, as they're something I haven't worn in several years. This means I might need to beef up my selection of leggings and tights.
The one striped top I am enjoying is a merino top with a slight cowlneck and longer length and sleeves. It's olive and grey, so I think I'll probably want some starker, "moodier" stripes for winter wear -- black/grey or black/white -- but not navy or brights. I like navy a lot in the summer, but wearing navy in the winter feels overly preppy to me.
This might also mean I have to stop lumping fall and spring together as one big "transitional" season. Even if the temperatures are the same, my mindset is not!