Oh, flannel shirts are a good idea Runcarla! A lot of my shirts are quite lightweight cotton or cotton/silk and, despite being long sleeved, wouldn't be warm enough for me on their own in the temps I'm thinking of. But flannel just might be!

Apologies, I haven’t read the other comments, so it may have been suggested already, but have you thought about coloured denim? More structured than joggers. I’m thinking skinnies or straight leg leans in a light colour like turquoise or mint green? Could you do printed jeans/cropped pants? There is a store here that does Liberty print items. I know you like Liberty print. Some Liberty print pants could be a good casual but interesting look.

ETA, a couple of examples of Liberty pants.

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I know this feeling with pieces that “should work” but don’t. And when they are essentials they do have to be right.

Probably 9 months of my year would be your transitional weather.

I think these pieces don’t have the fun or spark that your clothes tend to have - you could style them to have that - but they just aren’t quite you.

I am a fan of joggers and leggings. I feel good in leggings but never felt that way in skinny jeans. Fashion and style can be funny like that!!

Brooklyn these are good suggestions! The thing about jeans is I think on reflection I am really wanting something lighter weight than denim for a bit of variety once the weather warms up. I do love Liberty prints! Here, J Crew has a longstanding collaboration with Liberty prints items offered each season. For whatever reason I have not paid too much attention to any pants on offer but I will definitely look into that now!

Oh Sal, just realized that I lost track of responding to your comment! Thank you for commiserating with me about the difficulty of items that should work but don't! I think you are right that these items lack some kind of "me" spark. I am tickled to hear you describe my wardrobe as having a sense of fun as I can be kind of a relentlessly serious person. ;-p And yes to rocking the items that work for you, you are right fashion is funny like that but it's wonderful that we have so many options.

A bit late to this but I really enjoyed the thread so thought I should contribute.

Spring transitional dressing used to be really tough for me, I just had no idea what to do and and didn't have the clothes. But now it's become one of my favourite times!

So what do I do?
- Well, I wear a lot of black and navy in the winter, so my palette brightens up. White jeans, "happy" coloured tops (your happy colours will be different than mine, I tend to go for saturated things).
- My ankles come out. Gone with booties, out with fashion sneakers, loafers, oxfords, etc. Pants get rolled, and I start wearing crops.
- I'm a knit fan, esp for work from home, so I have several linen, cotton or silk 3/4 sleeve sweaters.
- And lightweight toppers and jackets get worn. In the winter I am wearing a coat, so unless a jacket is part of an outfit, it's not worn. Spring is when I enjoy wearing denim and leather jackets as outerwear.

I think these are all things one can do to "transition" regardless of your personal style.

Elizabeth P these are helpful suggestions, thanks!

I do need to up my spring jacket game. But, I don't really enjoy wearing jackets, and find them hard to fit, so a chore to shop for...