Mark McNairy's Red Brick Soul Suede Derby...$258.00
I promised myself I wouldn't geek out over McNairy AGAIN, but it's really hard not to. These shoes speak for themselves and are the perfect dirty buck in my book. Great color, red brick sole, goodyear welt, hiking laces, etc. Game. Set. Match.
Loake Royal Shoe...$196.00
I realize you can spend a ton more and get a pair of Alden or Allen Edmonds longwings, but I figured I'd do my best to even keep the high end on a short leash where I could. The Loake Royal in burgundy is a great looking shoe with a classic shape, a Goodyear welted sole and leather insoles. These puppies are bench made in England and should last you a very long time without forcing you to file for Chapter 11 immediately after you swipe your plastic.
Allen Edmonds Grayson...$325 or $525 for cordovan
I know, I know - these aren't true moccasins so please forgive me. I'm not the biggest fan of high end moccasins so for me a moc toe, tassled loafer is a great shoe for a sockless S/S. With that being said, I'm partial to the AE Grayson in the merlot colorway as I believe it adds another level of sophistication to an already sophisticated style of shoe. Talk about a great way to top off a casual kit.
The Boat Shoe:
Quoddy Deck Chukka...$274
If you are going to step up your boat shoe game I personally believe you should man up and go with a chukka version. Quoddy makes the hands down best in the game and odds are you already know why so I won't bore you by rehashing the details. I will mention, however, that if the white sole is a little too WASP-y you can always have it switched out for a camp sole.
The Penny Loafer:
Alden Leisure Handsewn Moccasin...$404.00
This is your classic Bass Weejun except it's on performance enhancing drugs. Much like all the brands on this list Alden's reputation precedes itself. The penny loafer is a classic silhouette that every guy should have in his closet. Dress it up or dress it down, it doesn't really matter. Remember to start from the ground up and if you have the money remember to start with Alden.