Carnival Monday and Tuesday 2020 is on the 24th and 25th of February.
Like shoes, it depends on what fete you are attending. For ladies, attire is everything. Looking good is one thing, but making sure that your outfit doesn't hold you back is another. Nothing should jump out, when you jump up or rip when you wine low. Shorts and a nice top always works and rompers are popular too, but with all the drinking bathroom frequent bathroom breaks may become a pain. Pack multiple bathing suits and incorporate them into your outfits. Men: shorts, cargo pants and a t-shirt or short sleeve shirts based on the type of fete.
Trinis tend to go from day parties to night parties to breakfast fetes and rarely sleep. According to how hard you plan on partying, try to sleep in between parties and schedule time to sleep during your trip (seriously) otherwise you may never get it and quickly crash.
It depends on the fete or event you are attending. The main thing to remember is comfort because you would either be jumping up and partying for 5-6 hours or on the road 'chippin', walking and wining all day. Fetes and parties. Ladies: For regular fetes, flats or sandals are best. You can get away with flip flops for Beach fetes. However, if you prefer to be somewhat protected from getting stepped on, a comfortable sneakers will do. Few ladies wear heels or wedges at the more expensive All-Inclusive fetes, but a nice sandals will do Men: Comfortable sneakers for fetes and loafer types will work for All-inclusive fetes. Slides/flip flop for beach fetes. On the road: Ladies: Comfortable, light sneakers to match your costume or a pair of boots. Men: Comfortable Sneakers. For J'ouvert, AMbush or any other paint and mud party, both men and women should get a comfortable pair of sneakers that you would not mind throwing out after.