My packing for the previously mentioned trip.. 

Surprisingly I got it all into a “international size” cabin roll-on..

Surprisingly reality hit me like a crushed ball of paper as rule #1 in packing is to make sure everything fits with some movement as the last thing one wants to do is get suits pressed etc every stop over.

So I went with my 3/4 sized check-in Rimowa Topaz (IIRC 24”).

Packing list:

• 1 navy 3R2 SB suit in 8oz Fresco
• 1 grey 3R2 SB suit in 8oz Fresco + extra trou
• 4 x light blue fine pin-point oxford hidden BDs
• 2 x white fine pin-point oxford BDs
• 1 x chocolate gingham BD
• 1 x indigo chambray BD
• 1 x blue oxford stripe BD (wearing)
• 1 x red/blue striped pima cotton polo
• 2 x grey pima cotton t/shirts
• 1 x khaki cotton chino trou
• 1 x white cotton chino shorts (wearing & not the same as yesterday)
• 1 x washed blue cotton shorts for the island
• 1 x dark brown 3 eye derby
• 1 x antique cognac 5 eye austerity brogue
• 1 x white buck with tartan trim saddle shoes (wearing)
• 2 x fast dry white v-neck under-vest that act as a wicking later so my shirts are dry & can then tolerate wearing a suits or jacket (great product from UNIQLO & cheap)
• 5 x fast dry fitted boxers (same properties as above)
• 7 pairs of navy with white dots cotton OTC socks (always pack as many as possible)
• 4 cotton knit ties, chocolate, navy, chocolate/grey stripe & navy/white stripe - again all from UNIQLO
• 7 various cotton handkerchiefs
• 4 various silk pocket square that are blue majority with white border trim
• various felt flower + lucky safety tie pin + caramel cotton newspaper boy cap
• & toiletries 

See you at the other end..