Top products from r/OUTFITS

Shirt: Uniqlo Slim Fit OCBD

Sweater: H&M Knit Sweater

Pants: Dockers Alpha Khaki Slim

Belt: Levis Double Prong Leather Belt

Polka Socks: www.target.com/p/merona-men-s-1pk-dress-socks-assorted-polka-dots/-/A-14623765#prodSlot=medium_1_3&term=merona+socks)

Shoes: Sperry Top Siders, Alternate

My go to trick with shoes is to match them to my hat. As long as the very top and very bottom of your silhouette match to form sort of "bookends", your outfit in the middle can have it's own color scheme, within limits.

Try a brown hat with a black band detail like this: https://www.amazon.com/Lisianthus-Women-Buckle-Fedora-Dark-Camel/dp/B07193Y16F/ref=sr_1_2?fst=as%3Aoff&qid=1566937079&refinements=p_n_size_browse-vebin%3A2343351011&rnid=2343347011&s=apparel&sr=1-2&th=1

I'm not sure about the quality since I really haven't heard of the brand, but there is a similarly styled watch to the Skagen you linked from Breda for $45. You can get a similar Skagen with a silver face and black strap for $77 at Amazon. I found a couple of others that have a similar styling to that watch but are above your price range, a Stuhrling for $78 and a Bulova for $90.