I'm slowly building my business wardrobe. Looking to get past my black shoes/black belt into brown. Looking for something versatile that could potentially work with a suit or also business casual. Maybe something that works with nice jeans as well. These will probably be my second and only set of "dress shoes" for a long time. Budget of $500 to $1,000 for both the belt and shoes together.
First Brown Shoes/Belt Combo Suggestions? $500 to $1k total budget
That's quite the budget for only one set of brown dress shoes starting out. I'd suggest getting at least two pair of them to allow for a rotation of 24 hours between wear (48 hours is optimal from what I've read from shoemakers, and is what I do - any shoe I wear regularly I have two additional copies of). If you only buy one pair, no matter how nice or expensive, you're going to prematurely wear them out. So at minimum consider two.
A belt shouldn't cost you more than $150 at the high end unless you're going into exotic leathers.
As is the standard around here, I'd suggest Allen Edmonds at the low end price wise, followed by Alden, Loakes, Meermin and the like, as they're all the minimum or more of construction quality, leather quality and goodyear welted. All re-solable, which you certainly want.
Beyond that general brand recommendation, it really depends on the styling you're after, and then finding that styling within each brand + price point to find your sweet spot purchase (of two of them! haha).
W/r/t styling and versatility, a cap-toe balmoral (closed lacing) oxford is the most formal, and works with business casual as well, IMO. However, to go all the way down to jeans a derby/blucher (open lacing) is preferable. The toe styling is up to you; many argue (well) that a cap-toe is the most formal (along with stitch cap, punch cap) but I personally find cap-toes most balanced and prefer them on all my lace-ups, regardless of the rest of the styling. Remember that the more brouging on the shoe, the more casual it becomes, in general.
Lastly (no pun intended), is last shape. The shape of the shoe is again a matter of preference. AE's and Alden's can be rather 'blobby' to some, but just right to others. Meermin offers a variety of shapes, and has a chart (couldn't find a larger version, search "Meermin last comparison"):
And finally here's a visual guide to general styling:
From there onwards you get into more elongated last shapes - see brands like Santoni, for just one example - which can work well with suits but not so much with jeans (IMO).
Remember though, comes down to what you dig.