please clarify "dressing appropriately"

[Darenda]

I read the information posted on this site for how to dress appropriately but coming from the US I am confused. Here is what it says:
"However, even the most formal restaurants on Tobago only request "smart casual". For ladies, this means no short pants and for gentlemen, no shorts, 3/4 trousers/pants, jeans, vests, T-shirts or other sleeveless tops. Flip flops and athletic footwear are also frowned upon for evening dining in the formal restaurants of most 4/5* hotels. Please note that you will seldom be challenged if dressed inappropriately, but will often receive a poorly-located table and low-priority service."

I do expect we will be dining more casually than formally.
1-Myself and my girls wear Sundresses (little shoulder straps), above the knee for casual dress and nice shorts (not cutoffs or holes) with sleeveless tops as acceptable casual evening here and our skirts are several inches above the knee, certainly not mini skirts but normal summer skirts for us...now I am worried they will be too short.
2-Will my husband and son really need to wear long pants for eating out? They typically pack long shorts (to the knee) with collor shirts/short sleeves
3-We were bringing flip flops and tennies for hiking around...

Just did not think about this issue and just stumbled across it making sure I had read everything! We certainly don't want to offend but also don't want to buy lots of new clothes for vacation either. Please advise. We arrive TH!! Thanks thanks, Darenda

[Paul Tallet]

It depends where you are.

I was thrown out of a small supermarket in Charlottesville for baring my chest

If you are in a Hotel it is generally expected that men wear trousers and a reasonable shirt ... shirt and tie requirements are rare. Ladies would be expected to wear skirt/trousers and blouse or dress ... but not a ball gown.

It's just about looking presentable in certain establishments.

In some areas, like Castara, nobody gives a damn.

However, it can be practical to wear trousers and cover yourself up in the evenings as there is an increased risk of being nibbled by sandflies in the more rural areas.

This isn't about extremes ... it's a minor thing to pack a dress and a pair of trousers for the evenings.

Regards

[Jan A]

I think that sundresses for you and your girls would be fine. Also capri pants would be great with light tunics etc. Nothing is very formal here. For the guys, dressy shorts and shirts/polo shirts with sleeves would be suitable for most places, but packing a least one pair of trousers is advisable. Hope this helps.