Help me pick a new pair of shoes

[Andrew Beck]

First, a little background. I live in work in Seattle. Work place attire in this city is VERY casual. I'm a software engineer and in the environment I'm in, it's even more casual than that. If I'm wearing a pair of dark raw denim, a collared shirt, and something other than a hiking boot, sandal, or sneaker; I'll be the best dressed guy in the office. However, I do like to dress nice without looking too out of place. My wife and I also tend to eat out at least once or twice a month in a restaurant where I can at least where a sport coat. And we go out to a very formal restaurant at least two or three times a year. Given all of that, here are the shoes I currently own

Blundstone 063 "Dress" Boot Black
Allen Edmonds Long Branch Brown Chromexcel
Jack Erwin Stan Double Monk Tan
Allen Edmonds Stafford Black
Florsheim White Bucks
Timberland Earthkeeper Brown Suede Driving Moc
Sneaker of some sort (I tend to replace every year, Jack Purcell, Chuck Taylor, Onitsuka Tiger, etc)
Blundstone Work Boot

During the week in the winter I tend to mainly wear the Blundstone 063s or Long Branches. It basically is either raining or threatening to rain from late September until July, so the rubber soles on them are helpful. They are both comfortable enough for the walking I have to do on my commute. I also find they are versatile enough to go with most jeans or chinos, even with a sport coat. Tough I wouldn't wear them with wool trousers. When dressing up more, I'll wear the Jack Erwin Monk's or the Staffords.

In the Summer, I tend to wear the driving moc a lot. It works with jeans, shorts, and light colored chinos. I wear the white bucks when I can, but that isn't that often. Depending on the rest of the look, I also wear the sneakers. When dressing up I tend to wear the monk's or the white bucks (depending on how formal and the rest of the outfit).

I feel like there are two major holes in my shoe collection. I don't have a real pair of black formal shoes and I don't have anything in dark brown that can be worn with trousers or a suit. I have a budget of about $250, but can stretch it if needed.

For the black formals I'm considering:

Herring Shipton II
Jack Erwin Joe
Allen Edmonds Park Avenue (shoe bank)

My biggest question about these is, do I need them? If I wear the Sanford's with a suit 99 out of 100 people would think nothing of it. The only things that I could foresee a need for something more formal would be a funeral or formal wedding; though I think the Sanford would work fine for most of those as well. The Sanford is also versatile enough to be worn with trousers and even dark jeans. As much as I love the look of the classic cap toe, I'm not confident I need them.

For the brown shoes I'm actually thinking about a brogue or semi-brogue in suede. I like the look of suede shoes and I think a suede oxford works almost as well dressed down with jeans as it does with a suit. The would also give me another option when a tan shoe just doesn't work or a double monk might be too flashy.

These are the four pairs I'm thinking about:

Herring Reading
Barker Albert
Loake 202
Meermin Mallorca Rapello

I am a little worried though about the suede with all the rain here, so if I decide against it I'd go with one of these most likely:

Jack Erwin Adam
Herring Surrey
Allen Edmonds McAllister (shoe bank)

Are there any shoes I should be considering besides these? If I do go the brown route is suede a good option? Thanks for all the feedback in advance.