What's your budget?
Not familiar with anything in that price range that I'd call "best". I wear Allen Edmonds. Not far outside your range depending on the particular style/model.
Seconded. If he can catch some on sale/clearance, he might get them in under budget, too.
several department stores carry good shoes near your price point. I recently got a pair of monk strap dress shoes and they look great with Jeans and with my dress pants. Just a thought. If you like your black shoes go with the same manufacture. Peace
Take a look at Herring Shoes - they are in the UK, but ship globally. They make higher end shoes (Churches and Loake) but also have their own house brand at a slightly lower price point. Well made, lots of styles.
The best I have found is Johnston and Murphy. I like them since their sizing is always spot on. I can order online and it is perfect. Dillard's and other finer department stores carry them. I love classic clothes and they are excellent. The best price I found (I searched the mall and online) was with Houser Shoes online. They were delivered timely and fit wonderfully.
I live in the UK and we have arguably the best choice of quality shoes available here.
There are many exclusive shops that cater for high quality men's shoes and I have a few pairs myself.
Oxblood wingtip dress shoes look very good. Smart and manly. They make quite a statement. As Liam S. posted the brands Churches and Loakes are high quality and within your price range. They'll last you many years if you treat them with care and you'll not regret buying them.
I also love Church's, and have several pairs, but at the $200 price point you mentioned you're within spitting distance of a custom pair.
Why not just save up a few extra dollars and have a pair made for you?
If your not too proud, which i am not, you can purchse used Allen Edmonds on line and have them resoled if necessary. There are great tutorials on how to strip and repolish dress shoes so you can have the above 300 allen edmonds for around 50-60ish range. I have 5 sons and have purchased some great shoes on line, refinished the uppers and they look great. I believe you are in the Army? Unfortunately most of todays military wears fuzzy boots and coraframs there may be a slight learning curve. New skill opportunity.
Hahaha your fuzzy boots comment was on point
thought you might like it. Look up Brogues, full, half, quarter. Full Brogues are wingtips. It will lead to other things be warned. I am on a kick about different types of dress socks, ties, and collar stays as well now. With a ton of sons it is easy to purchase and experiment with different items. I love the way a good pair of dress shoes feel and how they sound when you walk on a hard surface floor. I actually enjoy polishing shoes so it is not a chore to me.