I have the Moby baby wearing hoodie which is nice but not necessarily practical to use all the time (if gets spit up on we take a while to finish laundry lol). I also got a cheap maternity jacket with #2 so I might try that this year if it gets cold enough. Mainly I use this cover and then wear my own jacket or w/e. I like that I can use it with carrier or stroller. https://smile.amazon.com/gp/product/B0159VZBNA/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&th=1
Depends on if his big bro was carrying a backpack with our water bottles and snacks or not. If he was carrying his little backpack then I just wore it empty, sometimes just clicked around my waist and I let it flap down, sometimes had it empty in “backpack” mode.
If I had a big backpack that meant I was carrying him on my front anyway so I’d either keep it in place if I thought he’d need to get back in soon but if we were in a flat away from cliffs area and he was awake and wanting to run is stuff it in the backpack!
Also for winter I recommend a blanket/cover type thing... that way baby stays warm! I used this one and it worked just fine!
Bebamour Universal Hoodie All Season Carrier Cover for Baby Carrier (Dark Purple) https://www.amazon.com/dp/B0159VZBNA?ref=yo_pop_ma_swf
I just got this cover today, and I love it. https://www.amazon.com/dp/B0159VZBNA/ref=cm_sw_r_other_awd_j4zLwbDZ44QS1
It's still pretty lightweight, but layered with a little snow suit/bunting, etc it's nice and warm and gives a little extra protection from wind and rain. It'll also be perfect in early spring and fall by itself.