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My daughter is a fashionista so I always ask myself, "What would Kat say/wear/do?" This provides a lot of guidance and when we're together I ask her to be my fashion consultant and personal shopper. My husband serves the same purpose (in addition to many others). Kat helped me buy my first pair of overly baggy pants with frayed cuffs. When that fashion first came out, I swore I would never ever buy them. Ever. But I did. Then I bought another pair. I like them. But I still wear my skinny jeans even though they are out of style Kat gently tells me.

It struck me recently that I don't wait to go back to the states to buy clothes or shoes. I purchase them in Spain because I see what people wear on the street everyday. I wonder if that helps me fit in a little more. Or at least people might think I belong there even if they know instantly I'm American. Perhaps it makes me think and look like I'm more culturally knowledgeable.

I place most importance on being flexible, open to trying new things, and free to change my mind when it comes to my wardrobe and how I want to dress to be me. There are many facets of me and my wardrobe should express that.

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Thanks for this thoughtful note Andrea. It is really important to be open in so many ways, and trying new things, even just to see if it works. If it doesn't, no matter; and if it does, how exciting! Great way to approach dressing. Living in a fashionable cities too must help inspire you (along with Kat and your husband). That was one of the things I was missing when I moved to Plymouth-not as much inspiration for clothing that looked like me. When we lived in Lyon: oh la la! What a delight to see how the French women dressed!

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You will be amused or saddened to hear that my fashionista daughter has to lend me some clothes when I'm in New York this week because the little black cocktail dress I was planning to wear for her shower will not withstand the rain and 50 degree temperatures. I can't wait to see what I find in her closet.

I can imagine that watching the French women on the street was a free fashion show everyday. What fun!

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Oh my! I wish I could see what you were able to borrow from Cat! I bet you looked fabulous!

Can I suggest perhaps you need a new weather app for your phone that predicts cold weather more emphatically 😄😄. (Or maybe this is all part of your strategy to get to try other people's clothing for new ideas?) ❤️

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I got a new Anne Klein coat out of it because Kat doesn’t wear it anymore! That was a big score.

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Oh excellent! I hope you get a few more days of cold weather just so you can keep wearing it!

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Lovely post, Sabrina!

I have always struggled with clothing, and remember being bullied as a child for my clothes. What I looked like didn't ever feel important - as long as what I was wearing was comfortable (because it's the law) and practical (for cleaning out the chicken run, digging potatoes, climbing trees, making mud pies), well, that was enough! Even today I can't bear clothes which aren't comfy - I resist buying anything new, and wear things until holes become visible - and even then I won't throw those clothes away, but wear them for gardening, or for my casual job, or under a jumper (!). I recently noticed a hole in one of my two (only two!) woolly jumpers, which upset me because it's so new. New? Hmmm. In fact I'd bought it the Christmas before the Christmas we first hosted Christmas, which was the Christmas before Covid hit. Yup, I've had it YEARS.....

We've just got back from a work trip and a large proportion of my small wardrobe is still in the wash. Today I'm dressed VERY smartly (for me) in my newest (and therefore not yet saggy) pair of walking trousers and a man's orange and white shirt from a vintage clothing charity shop which had cost me a fiver longer ago than that holey jumper. A rare day on which I feel both comfortable AND presentable! 🤣

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I love this! You are the original slow fashionista! Very on-trend too :)

I bought a bunch of second hand cashmere sweaters over the years when I still lived in California. After we moved to Plymouth, they were a hug from home and so so warm in the damp climate. Unfortunately, the moths also took up residence and after a short while my sweaters were decimated. I've repurposed one into a vest top, and the rest have been cut into squares. I have a lovely long patchwork cashmere scarf, and am still considering what to do with the rest but I can't possibly let them go! So many of my clothes have been cut up into other uses when I adore the fabric. Some have become pillow covers, or embroidered adornments. I'm with you on having a hard time letting go of beloved comfortable clothes...

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Second hand cashmere is the best. It's my thrift shop go to.

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May 3Liked by Sabrina Simpson

A thoroughly thought provoking piece this week Sabrina - I love it! The topic feels somewhat like the chicken and the egg to me - roles, stage of life, where we are living: how do they all reflect or determine what we wear and in what we are comfortable? I’m not sure. But one thing that struck me is though you and I grew up living in the same Northern California environment, I find myself most comfortable in cool/cold weather clothes - cozy sweaters and scarves, warm pants, wooly socks, warm hats, gloves, boots and hiking shoes. I do appreciate lovely spring and summer dress wearing opportunities, and fancy clothes on occasion, but it’s not my go-to. Interesting! For more thought.

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I'm so glad you enjoyed it Martha! I think all these things are important, and at different times of our lives one or the other comes to the front. And certainly, if we are seeing people and out and about in social settings certainly affects what we wear too. I'm so delighted to know you have found the place that allows you to fulfil your cozy warm comfy clothes desires!

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May 2Liked by Sabrina Simpson

Bingo! I woke this morning here at the coast and wondered, will I wear the leggings and Lulu Lemon zip up I wore yesterday? Or will I pull out my one and only pair of jeans which means a T-shirt and navy longsleeved T-shirt because that's all there is in this tiny house. Does it matter?

No, it doesn't.

I won't see anyone apart from my gardener friend and she'll be in her worn coastal gear, just like me, as she potters in her garden and walks her dogs. It's who we are, we 'live' our dreams - gardening, cooking, walking the dogs (and in my case writing, her case painting and drawing hugely emotive floral works).

If I was in the city, it would be different - more classily casual - better shoes, jeans, trousers, tops, maybe even a swish-o scarf, handbag and coat and definitely earrings. I wonder why? It matters to me but I can't pin the why-fores down. Perhaps in town, I'm not authentic me, which means I have to hide behind something. Do I need therapy? Oh God, probably!

I'm so glad you wrote this piece, Sabrina because yes, I think where you are does make a difference for a lot of us. And what you are doing in the stage of life you're at. And shoes - comfortable shoes are the predicator of everything! But I'm still at a loss in my own case...

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Oh Prue, thanks so much for your thoughts and careful consideration of this issue! It was a very interesting week of pondering for me, and I threw out most of what I wrote as I rambled away in so many directions. I think all of the issues are relevant: geography, time of life, roles we occupy and so on. And certainly whether we are in company of others or not. And as to shoes, I am slowly migrating back to my beloved birkenstocks that I first wore when I was probably 16 years old. Such comfort for someone with wide, high insteps and narrow heels. And if your feet are happy, everything else falls into place!

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May 2Liked by Sabrina Simpson

I dunno, I always want to be wearing what you're wearing!

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We used to wear pretty much the same things didn't we?? Maybe it's you I'm missing to help me figure it all out! ❤️

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For most of my school life, the first 12 years, I wore uniforms and loved it, especially in high school. Being from a long line of fashionistas dating back to great, great grandmother per the photos I have, getting dressed every morning when I stopped having a uniform became daunting given the standards I grew up with. I do remember that in high school I was introduced into the concept of thrifting - cool clothes that were out of fashion which made them edgy.

Looking back on my fashion sense, I have always dressed with a classic style that had a vintage flare. I'm more aware of this because dressing in specific time periods - 18th century, Regency, Victorian, Edwardian, 1920's, 1930's - is a big part of my social life with my boyfriend. Perhaps I was always meant to do this.

I enjoy seeing someone who has a definite style no matter what it is. It's appreciating a well put together aesthetic. Thank you for giving us a fun romp into what we wear and what it may mean.

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