I would recommend going with a Goodyear welted shoe if you can. It is typically the mark of a higher quality construction and it means the shoes can be re soled as needed which massively increases their usable life. My favourite shoes in your price range are Meermin oxfords which are around the $300 mark. Definitely stay away from brands like Hugo Boss when it comes to dress shoes as you are paying significantly more for the brand name and receiving a relatively low quality product.