I have always put an outfit together by starting with one item —
and that item is usually either the sneakers or watch I plan to wear that day. Most of my clothes are gray, black or navy blue, so I dress in neutral colors and will add some color with a watch strap and/or shoes.
Even though it’s always good to buy a watch on the bracelet, I honestly wear mine on straps most often. I think straps can provide a good compliment to a watch and then coordinate with the outfit—especially a nice suede strap.
I also think that style is really about what you feel comfortable and confident wearing. Things are cool because you genuinely like wearing them. If you wear something just because you think other people think it’s cool, people can tell, and it doesn’t look authentic. If you like something, then wear it and who cares what anyone else thinks.