How to Buy a Pair of Men’s Boots

It’s simple. Walk with me.

Dean Casalena
Nov 2, 2016 · 15 min read

So you’re looking for a pair of boots and you don’t know where to start. You want something straightforward. You’re a minimalist like me. No fuss. Leather, though. Here’s what to do. It’s simple.

You look online. Maybe Nordstrom Rack has a good sale — black boots. Black goes with more things. If you’re going to spend over one hundred dollars on a boot, it should definitely be versatile that way.

How do you know if any of these are good quality. What does leather upper mean? A lot of them are too decorated. They should be straightforward — we’ve covered that — and durable. There are a lot to choose from. They need laces. John Varvatos, Ted Baker, Steve Madden — wasn’t he in Wolf of Wall Street? Ah, Wolverines! You’ve heard those last for 1000 years, and they’re half off. They’re straightforward. Black. Surely they’re leather. You should buy those. You do. Done.

While you’re waiting for them to be delivered, you do a little more research on Wolverine. They make a lot of boots. Heritage, 1000 mile — oh, only a few are 1000 mile. What did you get? Zeb — what does that mean? They’re not on the Wolverine site. Check Google — they’re not really on Google either. There’s something wrong with all these Wolverines. Their front-parts are really big and bulbous. Was Zeb’s front-part really big and bulbous? You think it was smaller — could be the lighting though.

Zebs arrive. Great new leather smell. Something’s definitely wrong though. The front-part is as much a Wolverine as the rest of their heritage boots. Try it on. Nice weight to it. Feels durable. The metallic little holes for the laces are nice.

But you’re going to have to return them. The front is ridiculous. Here an artists impression of how the shoes really looked, in a way photography can not convey.

Artist’s depiction of a Wolverine heritage boot

You probably shouldn’t have been caught so off-guard. You should have looked at their tag line.

Returning these by mail doesn’t seem simple. Just take them to Nordstrom Rack — you can buy a new pair right away. They’ll have plenty that fit the bill. Size 11. Leather. Black. Straightforward. Laced. Short up front, long in the back.

But really Nordstrom Rack has nothing. Boots end up at Nordstrom rack because their maker had tried out a boot decoration that didn’t sell. Or their market research flubbed the percentage of size 14’s their factory should produce. Straightforward boots don’t end up at Nordstrom Rack.

So you try DSW. They have palladiums but they’re too casual, and some timberlands for clowns, and Frye boots. You can tell they’re Frye due to how they use the outside of the heel, and the tongue (that’s the piece behind the laces) to proudly display their logo — as though somehow they’ve retained advertising rights on the item for which they’re allowing you to give them money. Timberland too. Do the emblems subsidize the cost of the boot?

Fashion statement: Advertising space for Timberland provided by: this clown who is wearing them.

No. Your boots can’t have a logo branded on them.

These boots all have different soles too. You wonder which of them can you walk 1000 miles in if you’re not a clown. Which of them are real leather. What’s vegan leather — that… doesn’t seem possible.

You should probably look some of this up.

It’s 11pm.

What else looks like a boot you would buy? Nisolo — how did you find this — are you being re-targeted by Facebook ads? Did you click a facebook ad? That sets a bad precedent. Now they’ll never stop. You’ve gotten yourself flagged as a sucker.

You visit Uncrate because you respect their style. WHAT are these!? Swoon. Viberg Service boots —appear to be unavailable— they were $740.

Viberg Service Boots — $740

Woah, the Nisolo’s are on Uncrate — but is this native advertising or a curated selection by Uncrate? Still, that’s an endorsement from a style enterprise whose brand image depends on not selling out, right?

Nisolo Lockwood Trench Boot Noir

There’s no emblem on these Nisolo’s. That’s a good sign. A plain front that’s not too bulbous, and gold eyelets (they’re called eyelets it turns out, and speed hooks). Black. Leather. Durable? They’re $248. That’s more than you were looking to spend. And you don’t know if they’re durable — they’re a young company — are they good? Are they the Brathwait Watches of shoes? How long will your Brathwait last — it still works. Looks good, that’s for sure. $248. They have any specials? “$500 for ten pairs of boots over 5 years with no limitations on selection”. Why!? Why would they advertise that their boots are made for less than $50 a pair? Are they desperate? Are they going to liquidate any second? How’s Brathwait doing? Some negative reviews on their newest model. Nisolo looks ethical — revitalizing a struggling industry in Northern Peru — You don’t know what Peruvian shoemaking tradition is like — is it good? But now there’s no way you could pay $248. Do you want to do the $500? That’s 20 shoes, or $25 per shoe. Is that even a fair wage? But you don’t know enough, I get it — no-one knows enough about this brand.

Your wife chimes in — says your friend (let’s call her Jia Min) has some Nisolo’s and loves them. You text Jia Min and she says she loves her Nisolo’s and that the CEO is a friend of a friend (which half cancels her endorsement).

You go to all the websites where you’ve bought shoes before. MyHabit — damn, absorbed into Amazon. You scour through everything at Amazon. Everything at Zappos. Everything at Macys. Google shopping. You reach the bottom of endless scroll on everything except Pinterest. You see a few boots that look good, and you’re starting to understand the pricing landscape and some terminology — toe box, structured toe, soft toe, plain toe, cap toe, moc toe, last (shoe mold), welt. Blake welt. Hand welt. Goodyear welt. Some shared style naming, like trench boot, work boot. Semi-Dress. Types and finishes of leather — Chromexcel, Roughout, Shell Cordovan.

A Goodyear welt is a strip of leather, rubber, or plastic that runs along the perimeter of a shoe outsole. The machinery used for the process was invented in 1869 by Charles Goodyear, Jr., the son of Charles Goodyear. Goodyear welted construction is time-consuming; invented hundreds of years ago, it is still considered one of the finest methods of shoe construction. The benefit of a shoe which is made using the Goodyear welt construction is that the shoe can be resoled repeatedly, giving the shoe a lifespan of years, sometimes even decades.(Wikipedia)

But you’re left without trustworthy endorsement of relative quality. You’re not trying to buy based on brand image, you’re trying to buy based on actual quality. Every site has reviews, but they’re all shallow. You squint as you try to understand why a website would include a 2-star average rating of one of its products public on the page. You start searching articles, menswear blogs. Lots of sneakers. Hype. No thanks. These boots need to last forever. Black. Leather. Unbranded. Gold Eyelets. Soft/unstructured toe. Dainite sole. Goodyear welt — which at this point goes without say.

You’ve formed an opinion on the cap toe — a crude an inappropriate way to finish the toe of a boot. The ultimate crutch of for the impatient, unskilled bootmaker. The blended scotch of shoemaking — a real patch-up job.

Cap toe boot. Made by a hack, necessarily

Plain toe is the single malt. Done once, in ancient tradition. Your boot has got to be unstructured, plain toe. That’s the definition of straightforward. Why overcomplicate it?

You stumble onto some comment threads that lead like breadcrumbs to a subreddit (forum) called goodyearwelt. 30,000+ subscribers. Post after post share your desires and concerns about boots.

A lot of them like Redwing — a work boot that has a structured bubble toe. They like Alden, Truman, White’s, Nicks, Allen Edmonds, Trickers, Østmo, Wolverines and Viberg. No-one trusts Nisolo yet. They post pictures of their boot collections at various angles so you can compare the toe and the width and their ability to age gracefully.

Dayton, Wolverine, Red Wing, Viberg, Red Wing

They post after one year of wear, after two, after five. They post photos of boot sales they went to, and you see they had arranged a meet up in New York last year when Viberg had a sale. You devour information. You participate, explaining your current progress, and goals.

They like Redwing Alden, Truman, White’s, Nicks, Allen Edmonds, Trickers, Østmo, Wolverines and Viberg.

Dozens upon dozens of people who have set aside the lifestyle of continuously burning through poorly made shoes, start offering advice.

It’s 5am.

You need to go to work soon. Your wife’s alarm goes off — she’s waking up for an audition. You summarize and convey your growing knowledge of boots and she admires your passion and doubts your sanity.

You go to work and start explaining the underground community of boot enthusiasts to your fashion forward coworker, lets call him Gungo. He recommends Oak Street Bootmakers. Again, he’s somehow connected to the owner. They seem to have been around longer than Nisolo. Handcrafted in America — a country you happen to love. A little more accountability, and feeding the local economy is good.

Oak Street Bootmakers Trench Boot

Black eyelets though. And $398. Still for a brand you’ve not heard enough endorsement for yet. Unbranded and meets the rest of the criteria. Slightly better than Nisolo, but significantly more expensive. Oak Street is also not getting much endorsement from goodyearwelt. Mostly for their pricing. They don’t carry the same pedigree as some of these other brands, but they’re still charging icon prices.

Gungo discovers a few of the same boots you’d had your eye on and you talk about it a long time. Then you talk about chef’s knives for a long time too.

Allen Edmond Higgins Mill Boot $350 is looking good (though the suede tongue didn’t strike me as straightforward)

Allen Edmond Higgins Mill Boot

Redwing is typically a bubble-toe, but they have a new model out called the Merchant Boot 8061 (sensing the style trend as you have). It only comes in Ebony and Olive. $319.99

Redwing Merchant Boot 8061
Merchants don’t drop things on their toes. They sell things — by being very stylish. So it makes sense.

Truman is stunning, but you’d be buying a fully custom boot here and waiting thirteen weeks. Incredibly, you can select every aspect of the boot, from the sole to the type and color of the stitching. $530-$1000

Truman — seriously visit this configuration page if you want to never be satisfied with non-custom ever again.

Nicks — same deal. $449–1000

Nicks, White’s, White’s
Nick’s wait time

White’s boots have a weird little heel-butt (not a technical term) and a very ugly website.

You go to Macy’s looking for Wolverines, to try to see in person if any of their models has a smaller toe. “1000 mile boots”, despite being made for clowns, (and even branded on the side) still resonates with what you’d consider high quality. Macy’s doesn’t stock Wolverines. But they do have the Allen Edmonds Higgins Mill boot — and it’s non-straightforward suede tongue is barely noticeable. The fit is incredible. The size 11 D width hugs your foot evenly and comfortably. $350 at Macy’s, but you know Allen Edmonds has a sale online where they’re $295. This rules the Nisolos out at $248, though $500 for 10 pairs is still a weird prospect. Would these Allen Edmonds really outlast 10×295÷500= five point nine successive pairs of Nisolo’s? Ah, but remember they might disappear. Right.

You work late because of all the talk of boots and chef’s knives, but you manage to make it to the Wolverine store on your way home before it closes. Their sales staff notice your Sperry’s and point out that Wolverine owns Sperry’s.

The elephant in the room is the gargantuan toe box in every damn Wolverine boot in the store. You pretend it doesn’t make you sick to your stomach.

After getting home, Jia Min texts “why do you ask” (if she loves her Nisolo’s) and you proceed into a long conversation with her about shoes. She says her boyfriend has a pair too but doesn’t like wearing socks so typically sticks to his boat shoes. She says her pair may or may not last forever, but they’re the first pair of shoes she’d consider getting re-soled. You ask if they have branding on them? The website shows no branding but in an unboxing video you watched—the unboxer points at a seemingly blank area of the shoe and mentions an emblem located there.

or she’s insane

You search the Nisolo website more intently, looking at your screen at a slant hoping to expose photoshopping artifacts on product images. You catch a break on their shoemaking process page — they slipped up. You can clearly see a hideous emblem.

Nisolo’s Chakana Emblem

Egregious. Jia Min’s have the emblem on them too. And you explain how that essentially makes them equivalent in every way to Crocs. She tries to encourage you to buy Crocs, and you can’t discern whether or not she’s joking. She suggests Wolverines and you re-use your joke about their tagline being ‘We make shoes for clowns’. She mentions the Wolverine Courtland —

Wolverine Courtland

It’s a moc toe — but in a weird way two wrongs make a right, and somehow disguises some of the toe box height. That said, by this point you already know that you wouldn’t spend $400 on a poor recreation of the $530 Alden Indy.

Alden Indy

You discover Viberg service boots are not as discontinued as you orginally thought, and they have a good looking boot made of kangaroo. It’s also Italian. Italian Kangaroo. $740

Italian Kangaroo Viberg Service Boot

You realize you probably wouldn’t be able to relate to most humans if you were the sort of person who bought Italian Kangaroo boots. Because you couldn’t pay your rent if you did, so you’d be homeless wearing Italian Kangaroo boots — pretty un-relatable. The Chromexcel version was slightly cheaper $690

Chromexcel Viberg Service Boot

They’re still $690, so it’s fortunate that somebody said Vibergs are terrible for walking long distances.

You email Nisolo to try to put to rest the branding/emblem issue, and also to find out if they’re goodyear welted. You’ve read rumors that they’re a blake welt — a style of welt that doesn’t have a forum named after it.

It’s late. Now folks on goodyearwelt are saying that goodyear welting is a good rule of thumb to a good boot but by no means the be all end all. You don’t know which way is up any more.

You start looking into Østmo boots, because they’re the slimmest toe you’ve seen so far.


They’re mind blowing — but made one pair at a time by a 29 year old guy in Finland named Lars Jensen. He has a cat and a girlfriend, and reminisces about his music-making days.

The Høstmo with the Østmo

He “self-taught [himself?] shoemaking in a little over six months”.

You’re reaching the eye of the storm.

You start considering moc-toed clown shoe, the Wolverine Courtland, if only to spite the depths of perfectionism you’re reaching — in the same way you sometimes throw away a receipt, just so that no-one can claim you’re obsessively keeping all of them, and you notice its stitching doesn’t wrap around the back — it’s a 270 welt, not a 360 — perhaps the one feature they shouldn’t have copied from the Alden Indy.

I wonder if these will ever show up first on Google when you type moc-toed clown shoe

Obviously absurd to consider this shoe knowing what you know. Gungo texts you and you take him through some of your um— process. He sends a screenshot of the liberally strewn branding on the wolverine.

You try to justify it by saying that it’s high up position would cause it to be hidden under the pant leg.

Stop. It’s $395. This is self-sabotage.

Back to the Allen Edmonds Higgins Mill. What was wrong with it again? The black boot had black eyelets. The suede tongue actually worked well when you saw it in person at Macy’s. Some folks didn’t like how Chromexcel leather patina’d, but you’re not sure if that bothers you. Some suggested pre-seeding the folds in your leather vamps by bending the front of the shoe around a pen. That’s not Chromexcel though, it’s Shell Cordovan — you’d know it anywhere.

pre-seeding the folds in your leather vamps (phrasing!)

You watch a video demonstration to be sure you’d have the right rolling technique. Folks are also saying no boot can be expected to last forever if you wear it every single day. A rotation between two or more pairs, allows the boot to fully dry (even from the dampness of your feet). So maybe you’ll need a black pair and a brown pair, and some shoe trees. The brown pair can lean slightly casual, and be these — the brown have the gold eyelets. The black pair can be more suit-appropriate, a different boot. These are still blazer-appropriate.

Allen Edmonds Higgins Mill

You sleep on it.

Nisolo emails back. It’s luck of the draw whether or not you get a branded boot. Maybe that’s their game. Sign up for 5 years, and for years 2–5 you have to wear shoes that have VISIT NISOLO.COM glowing out of an LED marquee wrapped around the heel. At least their 2017 boot model looks like it’s going to slim down that toe even further, and may be goodyear welted. Nisolo knows what’s up.

2016, 2017

You discover Alden 4515, a perfect black boot. 360 goodyear welt with plain toe and gold eyelets. The darker rim keeps it dressier than the Allen Edmonds Higgins Mill — a perfect complement. That justifies the purchase of the brown pair now — even if you can’t afford the Alden $550 for some time.

Alden 4515
Alden 4515

You pull the trigger on the Allen Edmonds Higgins Mill in Brown on sale for $295, deciding not to go for their factory-second option you learned of for $245. You start reprioritizing your budget (looking for a cheaper apartment to rent) to allow the purchase of the 4515 Aldens.

Allen Edmonds Higgins Mill
Allen Edmonds Higgins Mill
They’re very, very comfortable too. Leather boots are supposed to take a while to be broken in and to adjust their shape to your foot, but these were comfy from day one.

What’d I tell you? Simple.

This post was not sponsored by anyone, although Alden, if you’re listening, for a pair of black 4515’s with the gold eyelets, I would heavily slant this further in your favor, and not bring up how 270 welts are gross.

Thanks to Nic Vargus.

Dean Casalena

Written by

Minimalist. Technologist.