What brand(s) make the best suits and dress shoes?

You haven't mentioned a price range, but the best shoes I am aware of are probably St. Crispins, which are pretty much bespoke, and British. They are also $1000+, which is too much for me, and I would guess too much for you.

If you are willing to spend ~$350, which is a lot, Allen Edmonds shoes are made in Wisconsin, by real people, and they are extremely good. Even better, though usually more expensive, are Alden Shoes, made right here in Massachusetts.

The important things that make a shoe good are:

1.Quality of leather. A lot of shoes you might find at a place like Clarks will have a kind of shiny exterior that to the untrained they are well polished, but are actually made of scraps of leather than have been glued together and melted into whole pieces. Pretty much every shoe at Clarks is like that, if you want an example to train your eye. (That said, I'm wearing a pair of Clark's sandals right now, and they have served me well for years.) What you want is WHOLE GRAIN LEATHER. "Genuine Leather" is a meaningless term. You want whole grain, and you want leather that has been fully tanned by the manufacturer. The way you know a piece of leather has not been fully tanned is, if you see the side of it, the interior is blue-ish. Real quality tanned leather will be brown all the way through, but this takes time, so cheaper producers cut it short to save time and money. WHOLE GRAIN is the good stuff. Allen Edmonds and Alden are both whole grain. The other thing is having each piece be a whole piece.

2. Construction. The kind of shoe I would recommend for someone who lives in a place where it rains is called a Goodyear Welt. Basically, a shoe is composed of the top part (the "upper") and the bottom (the "sole"). In a lot of shoes, including cheap shoes, and most sleek Italian shoes, the sole is just stitched right to the upper. This makes the shoe look cooler, but it also makes it behave poorly in the rain, which is why Italian manufacturers DO do it a lot, and English producers usually do not. A Goodyear Welt is a piece of leather that is attached on one side to the upper, and on the other to the sole. So when you look down on a shoe made this way, you will see the stitching surround the outside of the upper. This is aa hallmark of this style: The sole sticks out a bit. There are two chief advantages to the Goodyear Welt: 1. It is very easy to replace the sole when (not if) it wears out. 2. Since none of the stitching from the outsole reaches the interior of the shoe (the welt attaches separately to the rest of the shoe) it will not leak water into your foot when it rains. I also just like the look, personally. #1 is handy, because all good shoes will wear out with use. Replacing a sole costs about $100. You should expect to want to replace a sole ~ every other year, if you wear the shoe daily. If you wear it only on special occasions, you can expect to go many years before repair is needed.

3. Comfort. Goodyear Welted shoes in particular tend to be comfortable once the leather breaks in and softens up. Allen Edmonds fills the interior of their welts with cork, which over time conforms to the shape of your foot. Also, nicer shoes have more sizing options so if, like me, you have a wider foot, you can get a shoe that really fits you.

4. Durability. A good pair of shoes, particularly the upper part, should have no trouble lasting you decades. There are nicer leathers made of horse hide called Cordovan (yes), and in addition to being largely waterproof and supple, are durable to last you the rest of your life.

The recommendation of Nice Shoe for the man who doesn't know what he wants is the Allen Edmonds Park Avenue:

http://www.allenedmonds.com/clearance/mens-clearance/shoes/park-avenue-cap-toe-oxfords/5875-120-D.html?utm_source=cse&utm_medium=google&utm_campaign=5875-120-D&CAWELAID= [login to see] 00387684&cagpspn=pla&CAAGID= [login to see] 9&CATCI=pla [login to see] 79&gclid=CNuH0bb4mM4CFdVZhgod5tADAQ

It looks like they are on sale now. I recommend these without qualification. I have recommended them to men who have asked similarly, and everyone is thrilled with them.

One nice thing about Allen Edmonds: Very common, so you can find them on eBay and save some dollars:

http://www.ebay.com/sch/i.html?_from=R40&_trksid=p2050601.m570.l1313.TR0.TRC0.H0.Xallen+edmonds+park+avenue.TRS0&_nkw=allen+edmonds+park+avenue&_sacat=0

If these prices don't intimidate you, and you want even nicer, just google around for Alden.

If that's not enough for you, you can try some of the British brands, which are truly excellent, and truly expensive: Crocket and Jones, John Lobb, St. Crispins, a few others. A British equivalent to Allen Edmonds would be Loake, they used to have some very well priced options, though they recently raised prices. But good shoes.

As for suits, I would try Brooks Brothers (also highly ebay-able). Not the best, but the beginning of The Good Stuff, durable, comfortable, quality materials, frequent sales. (The best time to buy from Brooks Brothers is in the spring and the fall when they have the "Friends and Family" sale. This is ~25% off everything, including clearance, which is already ~50% off, but also is the only time year-round things like oxford cloth shirts and navy blazers are discounted at all.)

Good luck, and happy hunting.

p.s. The best best best place to find deals would be a thrift store that is near a place with lots of very rich people. People who are very very very rich frequently buy very nice things, wear them once, and donate or drop them at thrift stores. You have to weed through piles of crap, but a friend of mine got a pair of John Lobb shoes his size at at a thrift store in L.A. for $30 that probably cost ~$700 originally. But you would probably need to visit a thrift store 10 times to get a genuinely good deal. I recently bought a Burberry lined trench coat for $35 at a second hand store in Gloucester, MA. It happens. But it takes patience. Like I said, you will have the best results knowing what makes quality quality, rather than going by brand. Some brands, like Ralph Lauren, make extraordinarily nice clothing, and also throw-away crap, and they are all called "Polo." Going by brand could buy you some expensive crap, so learning what a good fabric feels like is the fast path to big scores. It can be hard to know which names are actually British Savile Row (really good stuff) but if you know what good shirt fabric feels like, you can mine the thrift stores.

Also: Ebay. Ebay Ebay Ebay.

SGT (Join to see)
Tailor/custom made! I got a tailor-made suit in Thailand my last deployment and it is the best suit I've ever owned.

I've also heard that Second Hand/Thrift Stores and other places like that, in rich neighborhoods, will sometimes have the "designer" suits (Armani and the like) in stock because the kind of people who buy them replace them every few years when the new line comes out.

For suits, a personal tailor is always going to be the best quality and give you the best fit. if you have a long body go with three buttons. If you have a short body go with two bottons. No vest is always in. Vest is sometimes in so don't waste your money. Get a navy blue suit if you are only going to get one. Just say no to pleats and cuffs.