Hi joy07,
Pre Winter or Post Winter are u gg ?
We went Japan every year from Nov till Dec so tis wat i dress up my boy :
1st layer : usual home PJ ( long sleeves & long pants ) with singlets & underwear / pampers
2nd layer : thermal set ( long sleeves & long pants )
3rd layer : home clothes short/long tees & long pants
4th layer : fleece coat sleeves zip-up & winter pants
5th layer : thick winter coat
Son wore CROCS winter mammoth linear ( from overseas spree ) and woollen socks and bought thin socks to wear as 1st then woollen socks ....... son's " winter boots " are his CROCS sandals !
Trains regardless JR or subways ain't stroller friendly as nid to carry UP the stairs and the lift is as small as HDB store-room SIZE !!
I was taught by another mummy in SMH to wear 1st layer usual home PJ as not all kids LIKE thermal material and kids may complain NOT COMFY so I did wat she taught me and even my boy complained , i only removed 5th layer when indoors.
I added on extra thicker tees btwn 3rd and 4th layers ......... my son wore like tt since 2.5years till last year ! Last 2years we went Nagano for skiing ........ we bought GAP winter coat for him tt can last till many years coz' can't find in local GAP stores !
Every year , we SURE go to Japan UNIGLO to buy HEAT TECH turtle neck thermal wear ( NOT AVAILABLE in Singapore stores ), cheap & affordable with Disney characters ..... and other winter clothings for myself & hb. UNIGLO on Fridays ~ Saturdays confirmed all stores have GOOD DISCOUNTS !!! We love UNIGLO JAPAN then hates SG Uniglo !! Japan Uniglo service staffs if dunno English, they will dig staff tt understand simple English to serve u with all yr queries answered !!
Ex-rate drops then can SHOP till u drop in JAPAN ! Japan has NO money changers like SG ...... Japan authorised money changers are the BANKS !!
Every year son's winter clothings pack in 29" trolley with pampers during younger days, milk powder, etc .......