Simply the Best: The Top Footwear in Every Category
Going back to the very first review posted on 100wears.com, this website has always focused on value first and foremost. Comparing a $50 sneaker with a $900 sneaker isn’t just not fair, it isn’t useful. But sometimes you just want to know: what’s the best thing out there, period?
We’ve all asked ourselves some variation of the same question. Maybe it’s “if there was a fire and I could only save 5 pairs.” Or, “if I had to move to a shoebox-sized apartment in NYC, which pairs would I keep with me?” If cost didn’t matter, which shoes would I keep?
Let’s set the ground rules.
First, while many of these pairs are expensive, simply being the most expensive doesn’t win you any points. Indeed, if I knew that I paid several hundred dollars extra for a pair that doesn’t do anything better I’d feel like a bit of an idiot. While good value doesn’t help you here, high costs for the sake of high costs can definitely hurt.
Second, this is entirely subjective to my personal preferences. If you disagree, let us all know why in the comments!
Disclaimer: Some of the pairs below were provided at no cost for the purpose of a review, but no brand was informed this list was being created, nor was any compensation asked for or received to be on the list. Everything listed below is true to my opinion.
Casual Sneaker: New Balance 991v2
Why is it the best?
What sets the New Balance 991v2 apart from every other casual sneaker is the amazing balancing act it does between looking like a retro runner while offering maximum comfort. All too often, sneakers need to choose one or the other. I personally love the style of the Jordan 5, but it feels every bit of 35 years old when you wear it. On the other hand, the Nike Invincible is incredibly comfortable, but the comfort-at-all-costs designs mean you’d look silly at the neighborhood cook out.
The New Balance 991v2 offers 95% of the style of any retro out there while offering 95% of the comfort of any modern running sneaker. My pair has been on business trips to Asia, tourist trips to NYC, casual Fridays, and late-night Target runs. I’ve even run a few 5ks in them when luggage space was tight.
Even better, nearly every pair is made using extremely high-quality materials in a factory with high labor standards.
What would I change?
While I love the New Balance 991v2, one thing that bothers me is the few areas with obvious cost cutting. Some of the changes from the V1 – such as having the sticky rubber pods lose their encasement – seem out of place on a sneaker at the very top of New Balance’s line up.
Other pairs you might want to consider: if you prefer something with a bit more squish, the New Balance 990v6 might offer all the same benefits.
Dress Sneaker: The Crown Northampton Harlestone
Why is it the best?
I don’t think I’ve ever been as surprised about a shoe as I was with the Crown Northampton Harlestone. The combination of the sneaker outsole and pattern combined with the full leather insole and cork footbed offer a feeling I have genuinely never felt in any other pair of footwear. They offer spring back like modern day foams, structure like a dress shoe, and a custom fit like a work boot. These are not just comfortable for a slim sneaker; in some ways they are the most comfortable pair of footwear I own.
The icing on top is that these can have their outsole replaced for a pretty reasonable $116 – including shipping to and from England.
What would I change?
The weirdest thing about the Crown Northampton Harlestone is that it would be better if it were worse. As their flagship line, Crown Northampton makes it a point to put only the highest end leathers for the uppers – but those same leathers go against the amazing feeling underfoot. I would love to see a Harlestone made with the soft calf leather they use on their GAT.
Other pairs you might want to consider: It’s a bit cliché today, but the Common Projects Achilles offers a more contemporary design that will still stand the test of time.
Casual Boot: The Russell Moccasin Backcountry
Why is it the best?
From the moment you first hold them in your hand, Russell Moccasin makes an impression on you. You go from saying, “$850 for a pair of boots that are not even goodyear welted?” to “Oh, I get it” in about 5 seconds. Nearly every other pair of shoes you’ve ever held had some form of cost cutting here or there. Not these. Every stitch, every cut of leather – crafted to perfection.
You also can’t miss the comfort. Moccasins are what got me into collecting footwear in the first place, but the flat construction meant I had to get rid of all my pairs as I got older. These, however, managed to be both flexible and supportive.
What would I change?
Honestly? Not much. If I was going to nitpick, I would encourage the brand to better clarify between shoes made under the old management and the new. There has been a major quality increase, and it would help buyers avoid older, more problematic pairs that are still sitting at retailers today.
Other pairs you might want to consider: The Alden Indy is a boot that will offer incredible versatility in style and is probably available to be picked up in your nearest city today.
Work Boot: White’s 350 Cruiser (or Bounty Hunter)
Why is it the best?
There are a lot of Pacific Northwest bootmakers, but most share the same materials and even trade workers between brands. Some do more marketing, some less — but if you want the most durable build in the business, White’s is the only game in town.
Combining the resoleability and upper protection of welting and the weather resistance of stitchdown, White’s “Handsewn Stitchdown” construction is everything you can ask for. Personally, I find the Baker’s Bounty Hunter (another name for the 350 Cruiser) the best looking way to get it.
What would I change?
If I was president of White’s for a day, I would clean up their ordering process. It is impossible to order the right pair you want without researching for hours.
You can order directly from White’s, but with limited options. Or you can go to Bakers which has different models available and a huge selection of options. Or you can find really unique make ups at Division Road with styles unavailable anywhere else, but with no widths.
Other pairs you might want to consider: Wesco, being located hundreds of miles from the other PNW boot brands, also offers a more unique take on the style.
Loafer: The Grant Stone Tassel / The Grant Stone Traveler
Why is it the best?
While there are brands that have more classic designs, and brands that have higher end finishing, when I’m in a rush to get ready and I’m looking for a loafer there is one that is my go to: the Grant Stone Tassel. As a piece of art, these are not the best. However, Grant Stone did something nobody had seemingly done before – designed a loafer shaped like a human foot.
There are other redeeming features as well, of course. My pair is nearly 5 years old and hardly looks worn. I have no doubt in my mind that these will last me for a decade before even needing a resole. Who cares that they’re affordable – they’re my pick for best.
What would I change?
One area where the cost cutting can be seen is the outsole. Sharing the same pattern as their boots and chunky dress shoes, the outsole is chunkier than I prefer in my loafers which limits their versatility with things like shorts. I’d love to see Grant Stone offer something specific to the loafer line that allows these to more seamlessly go from casual suit to swimsuit.
Other pairs you might want to consider: If you value classic design over comfort, the Alden Tassel Loafer is the definitive tassel loafer pattern.
Dress Shoe: The Crockett & Jones Connaught
Full Review Coming Soon!
Why is it the best?
This pick might surprise some – I own pairs of Edward Green. There are even higher end options made by Crockett & Jones. Why would the Connaught be on this list?
Well, the simple reason is that these do everything you could possibly want from a pair of dress shoes. The leather looks great new and worn in, the last is perfection with a business suit, the comfort is excellent, and there isn’t a single stitch out of place.
Of course, there might be specific reasons you want to splash out a bit more, but for me, going beyond the Connaught is simply throwing money away just to say you did.
What would I change?
Crockett & Jones does an extremely poor job in offering widths. Not only do most models only come in one width, pretty much nobody in the United States carries them. Expect a lot of back and forth with returns. Or a trip to NYC if you really want a pair that fits.
Other pairs you might want to consider: The world is really your oyster here. If you find that Crockett and Jones doesn’t meet your needs, leave what you’re looking for below and I’ll see if I can help find a pair for you!