Those Rubi pocket squares have wonderful color combinations for true versatility. They aren't a thick silk, which makes them less bulky in your pocket. I have the Victory but could easily use a couple more.
Neither of the last two jackets with the shirt and tie shown in your fit photo.
The plaid patterned blue jacket is nice. You could wear it with a pink shirt and off white or grey trousers or nice jeans and a white shirt.
With the off white jacket, I wear mine with either light grey pants or jeans and a blue or pink shirt.