A friend of mine is a hobby sailor who takes a large yacht out onto the Philadelphia Eagles Super Bowl LVII Open Sky Shirt but in fact I love this Kattegat in all kinds of weather. He told me once that staying warm in the conditions as encountered there (fitting your description very well) actually comes down to a formula: Basically, he suggests dressing as follows for the upper body, from close to the body to further away from the body: The thing with the legs is that they tend to get wetter, so they need to dry fast; also, you don’t need as much insulation on your legs as you do on your upper body. I use his formula here in northern Sweden, and go out exactly with these layers even at temperatures down to minus 40 Celsius, and I am perfectly comfortable with it. You can wear whatever you want to wear. Age is irrelevant. Some will like it, whatever it is. Some won’t. Some won’t care. Some will see only what they want to see. Some won’t even “see” unless it bites them. You are talking about NORMAL daytime temperatures in Sydney, Australia in late January so I am very used to this. Normally I either wear my swimmers and stay in my pool – preferably close to the swim up bar – or I wear shorts and a tee shirt and stay inside in the air conditioning! How many layers I wear depends on the temperature. So, today it was really nice, 22° C with just a nice breeze off of the bay. To me this is perfect summer weather. Not to hot, not to cold and my first official day back in the office. I wore my kahki skirt, white V neck tee, sneakers w sneaker socks. I also brought a little denim jacket with me this morning (7°C), we’re right on the bay, so even the hottest days it can be cool in the morning. Basically 1 layer, 2 if you count the AM.