I took a quick look at www.ashford.com
and they seem to have a lot of decent watches in the "Under $300" category (including some nice looking Tissot, Seiko, etc).
Although i'm not an expert on this, another route maybe going with somthing vintage (authentic vintage and not simply "vintage looking"), however, this may come at a higher price (really depends on what you're looking for). In my opinion, older watches tend to have a timeless appeal that is lacking in many lower-end present day styles. Vintage watches, however, may need to be serviced/overhauled, may need more ongoing maintenance and replacement parts, and you really need to watch out - probably easiest and safest to buy from a reputable seller who knows his stuff.
Again, just my $0.02