Get thee to ebay.
Used Florsheim or Allen Edmonds. Should cost you around 40-60 for a well worn pair in good shape.
Take to cobbler. Should cost about 20-35 for resoling, polish and waterproof.
They will look 10x better than anything you can buy NEW in that price range, and last 4x as long.
Be careful when you buy the shoes, though, if you're going this route.
Check feedback rating (always)
Only buy from US buyers (shipping will kill you)
Check for gouges and deep scratches on the uppers, cobbler can't fix those. Same thing with most kinds of stains.
Mind they're not too creased, may mean they weren't conditioned and could be cracking.
Feel free to PM me for pointers if you find some you're not sure about.
Best of Luck,
Upgrade from what, to what?
Are you looking for dress shoes, loafers, casual, boots, or what? And, there are some regional style differences...I live in Texas, and a well polished cowboy boot is appropriate for dress, here.
What are you looking to buy?
My favorite brands for dress shoes are often British. Church's is exceptional. Allen Edmonds is amazing, too.
Let's start out with a more basic question. Do you know how to identify quality?
Upgrading from Vans and Converse to nicer casual shoes and dress shoes. I'm looking to learn more about quality; I've been reading up as much as I can, but I'm still not entirely sure what to look for.
I live in Texas too (College Station), but I would look just silly in a boot. It's unfortunate because I'm part of the Lucchese line and my brother works for them.
When you say casual do you mean the traditional casual, e.g. brown oxfords, desert boots, loafers etc, or do you mean more adult sneakers?
There is a huge difference.
My bad. Traditional casual.
Why would you look silly in a boot? It's all in the attitude...own the look, and you're fine. I didn't say cowboy-up...you don't need the turkey platter sized trophy buckle, or the Wrangler clothing. But, a nice pair of boots, and Lucchese boots are exceptional, are a design classic. Lots of choices ranging from the "beginner's boot" Justin roper:
to something more upscale like this beautiful Lucchese exotic:
For a first pair, I'd go with something a bit less expensive than these, but aren't they beautiful? I genuinely *love* cowboy boots.
You see, I felt the same way as you do, for decades. (I'm 41) I could never wear them. They're only a work boot. Won't I look too cowboy? But, I live in the city! (Dallas, at the time) But, once I found it within myself to wear a cowboy boot, I've never looked back.
Now, let's address your questions, specifically:
1) Sneakers. Converse Chuck Taylors are considered a design classic, and actually look both youthful and appropriate with a lot of different casual outfits. Youthful...but grown up. They're a great design, and if I'm not mistaken, there's a Converse outlet in your area. The idea is that it's a simple, fairly plain design classic.
Conversely (pun intended), the latest Nike or Reebok moon-boot just looks weird and, while appropriate for the gym or playing football with your friends, they're not appropriate for general wear.
I tried on a pair of ReeFlex shoes the other day, while I was in Dallas. Very comfortable, almost felt barefoot. But they were fluorescent chartreuse green. Words like fluorescent and chartreuse should not be uttered, on a men's style blog.
One trick to keep sneakers looking appropriate, is to keep them clean. A nice, well kept sneaker of simple design looks nice, even with a pair of khakis, or even a suit (David Tenant as Dr. Who) But, dirty, muddy, and smelly is never a good look under any circumstance.
2) Casual shoes. This could be anything from the "brown suede sneaker" by Skechers, to a rubber soled "dressy" shoe. It depends on what your goal is. I actually do have a pair of those relaxed Skechers, and I do wear them with something like khakis...they look a bit more grown up, without looking like I raided my grandpa's closet.
3) Boots. Lace on or pull on are the choices. You are part of the Lucchese family, and you're living in Texas...embrace it!!! I can't believe we're having this conversation...get some boots!!!
But, if you're not willing to do that, then get a good pair of work or casual boots for when the monsoons move in. Wolverine makes some sweet choices. If the prices are too high, then there is the used market (eBay) that was mentioned earlier, OR just buy them online. Stores like Zappos and SportsmansGuide are great!
4) Dress shoes. Spend some money here. They're not stylish...they're classic. And classic is the word you want to remember. These are shoes which, 10 years from now, will still look just as good as they do today. Frankly, $100 is the low end for this category, and rightfully so...save up and buy GOOD ones. Materials of this quality...matched hides, leather linings, etc cost money, and you'll have to pay for that quality.
General rule of thumb is to keep the style classic, the soles thin (leather or very thin rubber), the lines fairly delicate, and the leather of impeccable quality. I mentioned Church's shoes, earlier. Here's a picture.
BTW, Lucchese has made some really sweet dress shoes. I have a pair...will have to take them out and post a photo.
I'll second the vote for boots. You're in College Station, TX. Boots are appropriate for all occasions ... from weddings (black dress boots) to mowing the lawn.
I'm in Houston. I started wearing them last year sometime ... from lounging around the house, to office attire (I'm an attorney). Comfortable. Durable. Looks sharp enough. I'll never go back.
You're not going to get any boots worth wearing for $100, though. You're looking at $175 on the low end. Still, they last forever.
He said he's part of the Lucchese family, and his brother works there.
I'd be willing to bet his brother could get him a pair with an employee discount...and they're often on sale at the local Shepler's store. Should help with the cost issue.
It's likely. They made my brother, mom, and dad a custom pair. Would probably do the same for me if I asked.
Custom pair?! You've just moved up into the $400 range, minimum, per pair.
One thing about good cowboy boots...they're made to a higher standard than most dress shoes. Even in the stuff available off-the-shelf, the quality of the leather, the matching of the hides, the use of the natural patterning, etc is all several steps above that available on anything but *the* most expensive custom made shoes.
You've got an "in" with one of the premiere manufacturers in the world. If *you're* not going to use it, tell me where to send *my* measurements...
I wear a pair of highly polished Lucchese with my Tux..own the Look!!
+1 for the custom boots. That is a great opportunity. I'd get several pairs.
If you buy (new) department store dress shoes for $100 you're wasting money. Probably be in the trash within a year.