For me - the answer is easy PLAID and RED!
With the impending change of seasons, I have noticed my temps are falling and the days are getting shorter.
I have bought for the season ahead - my JCrew Stewart tartan items are from 2020 Black Friday sales, bought in November. I was pleasantly surprised that the blazer is lightweight, and I went for the cotton shirt. This gives me a 'winterish' look without too much warmth which is best for the next few months. When things get cold, I can layer on the scarf.
My other purchases have been second hand from Japan - purchased online through a Japanese company called Zenmarket.
My second hand purchases from Japan have been in immaculate condition. I really like one second hand retailer called "Secondstreet" and so far have stuck with buying from them. The shirt and one of my bags were classified as B grade by Secondstreet - but there is minimal sign of wear. They cost about 10% of the new retail price - so that red tartan bag that would have been about US$400 was US$40. The other items were new with tags and were purchased for about 30 - 40% of the tagged price. The cape, bought new direct from Crestbridge (or Burberry Blue - Japanese made under licence from Burberry) and shipped by Zenmarket was on sale at 30% off and is my wildcard purchase for the winter season. It is totally reversible - with the check pattern on the other side and the faux fur collar is removable - giving me 4 different ways to wear it.
I did not need another bag but had a gift card that was due to expire in a large local department store. It was a pretty sad state of affairs wandering around the store looking at all the tired end of season merchandise. Luckily I found the red bag, new season stock that actually looked new. It is a great colour for my wardrobe and so whilst I had not planned on buying another bag - this one came home with me and I love it.
This year I have done more purchasing in advance of the season than before but tried to be planned with my acquisitions. I will wear these working from home. I am hoping to add some new jeans or trousers into my capsule and possibly some low heeled red boots. No new dressy clothing is allowed, I am well catered for on that front.