I have these,http://m.nordstrom.com/s/3545308/?cm_cat=datafeed&cm_pla=shoes:men:boots&cm_ite=prada_chelsea_boot:926749&cm_ven=Google_Product_Ads&mr:referralID=f8001098-376b-11e3-bae4-001b2166c2c0
I wear them fairly often casually, but couldn't wear them seriously with a suit. They are primarily tapped for night out on the town duty.
I really don't like shoes that look like they're super polished patent leather. Those are also way out of my price range.
Black shoes aren't great for casual - if I were wearing black with blue jeans, it would have to be something like a heavy scotchgrain, perhaps with a thick welt or heavy sole. There is no one shoe for everything, and this is not the place to find people who will advise you to buy fewer shoes....
Of the two, pick the AE because it will actually be smart enough to wear with a suit, and it's a better-made shoe. But assuming that's around the $300 mark even in the sale, I suggest this: if you're on a budget and that's why you only want one, then email firstname.lastname@example.org asking them what they have as seconds in your size (see above comments on size guide, or go into an AE shop and get measured./try stuff). I am sure you will find some sharp black dress shoes and somethign better to wear casually, maybe even a boot or two, and get both for under $300.
The AE seconds are 250ish and I just found out they don't have my size in the bank so nevermind... I'll wait for a 2 for 250 sale.
I don't mind buying used as well, so lets see. Thanks for the response.
You'd probably be better off buying two pairs of boots - one which goes well with suits, and another which goes well with jeans.
I know you'd like to find one pair which goes well with everything. Unfortunately, you're much more likely to wind up with one pair which is a mediocre match for everything, and an excellent match for nothing. It's like buying a Swiss Army knife, because it gives you 47 tools in one. Sure, it's convenient and inexpensive, but none of those tools is likely to be as good for the job as a single, "normal" tool.
Since quality footwear, properly cared for, can give many years (decades) of use, this should be one area where spending a little more upfront, for excellent quality and excellent suitability to the role you wish the boots to play, makes sense. It's not like you'd be blowing hundreds of extra dollars on an item which you'd only be able to use a handful of times, before it grew worn out and had to be replaced. Quality footwear can be thought of as more of a long term investment.
If you absolutely, positively cannot purchase two pairs of quality boots, I'd recommend you decide which is more important to you - wearing with jeans, or wearing with suits - and buy one quality pair for that one purpose. Then, later on, when finances make it possible, buy a second pair of quality boots for the other, lesser, purpose.
I kinda have two pairs of black boots. I bought a pair of used CH black 'waterproof' chukkas that turned out to be defective and I glued back the sole and they're working fine for now. I think I might be set with the Aldo's I got. I'll post a picture later.
As far as thinking long term, I have a pair of AE walnut daltons I bought used which I expect to last me for the next 5 years atleast. I could pull off a suit with them if I had to. I also have a couple of pairs of brown zip up boots that I could wear with jeans. I like black boots with black jeans though, which I do tend to wear. I also like wearing black shoes/boots with khaki's and dress pants when I go to work.
I have a bunch of other dress shoes too that I've sniped on ebay and they're all in good condition. A few of them might not be resole-able, but a few of them are actually pretty nice made in USA or Italy J&M's.
I'm kind of at the point where I almost wish that I could exclusively wear boots. So lets see what happens.
If anything, I have too many shoes. I should probably wear out and toss some of the meh ones though.