I've been wearing a pair of Daniel Wellington watches but on changed straps (a silver number with a black goat strap and a rose gold number with a brown croc strap - both white dial) and a number of people have mistaken them for something much more expensive (the watches with original calf strapes were circa $180). Looks formal enough for any place and is ok for dressed down too for anything more than t-shirt/shorts or sweats.
Have some no brand steel quartz number for purely activity based holidays.
Personally don't like sports watches like a Rolex Sub with a suit and so more likely to take a dress watch with me (and at their price DW are good as I wouldn't mind if they were lost) and just not wear it on the beach etc than take a sports watch and go without a watch if going out in the evening or such.