Dress Like A Millionaire: The Handsomest Shoes

A weekly segment in which we capture the Downton Abbey look at Roseanne re-run prices.

Here in the northeast it seems equal parts naïve and hubristic to contemplate premium leather foot cover as four months of salted surfaces, frozen AND salted rats (if you’re lucky enough to live in New York) and manic, depressive weather pundits loom ahead. However it’s never the wrong time to buy a truly high quality shoe and even if you have to make use of contraceptive devices, well made footwear will weather any conditions better than it’s pilgrim-toed, reflective, down market brethren. Terms like “bench made” (whereby all or part of the shoe construction is done by hand by several different craftsman at separate “benches”) and “full grain calfskin” (as opposed to “polished calfskin” which uses imperfect or lesser quality leather, shaving off the top layer to rid the skin of the flaws and then applying a chemical finish to make up for the loss of integrity) are not just being spoken around silver spoons these days. As the men’s wear blogosphere began its heavy breathing over all things “heritage” and American made, existing makers of fine cobbling have expanded their offerings to embrace some sleeker sillouettes and new players have entered the fray with non-hedge fund pricing. The three shapes and the 6 essential brands (both caviar and canned tuna priced) of truly great shoes:

Wingtips from Church's and Brooks Brothers

For your reception at Buckingham Palace don’t forget your wingtips by Church’s; for every single other occasion Brooks Brothers’ version will more than suffice.


Along with John Lobb, Crockett and Jones, and Tricky’s, Church’s forms the British royal family of shoes for the discerning, making a case for propriety below the ankle for over 300 years now. Investing in the very best materials and craftsmanship outside of the bespoke world, they can very nearly do no wrong and their wingtip is an investment in looking properly appointed for years to come. Brooks Brother’s version will be nearly twice as easy on your retirement plans and is still made in the USA featuring French calfskin and Goodyear welt construction.

Monkstrap shoes from Crockett and Jones and Allen Edmonds

When negotiating trade sanctions with Bolivia don’t leave your Crockett and Jone’s monkstraps behind; for more local transactions Allen Edmonds has you covered.


Simply because it’s probably the fourth or fifth shoe you should buy after solidly covering your wingtip, bucks, and boot bases, the monk strap is by it’s very nature a 1 percenter shoe which is all the more reason it should be courted at the highest levels. Crockett and Jones who are possibly even more aristocratic than Chruch’s simply because they seem that much more willfully ignorant of trends, offer up a stunning ruddy, chestnut option with this single monk (contrary to nearly every other male voice on the internet, I read something a little bondage-happy in a double monk). You’ll have to try it on in person at one of their retails locations however, since the honorable Misters C&J don’t deign to leave service in the grubby, plebian hands of the internet. On the other hand Allen Edmond’s has been kind enough to put their boot-inspired option on sale. Both are beautifully finished with full leather soles and premium calfskin uppers and are just as likely to turn heads at your office as they are at the UN Security Council.

Boots by Alden and Wolverine 1000 Mile

Need to tell your stable hand to muck out the horse stalls? Put on these boots from Alden. Need to tell the deli guy how you like your coffee? Put on these boots from Wolverine 1000 Mile.


Contrary to what most magazines and vast swaths of the internet will tell you, the majority of boots just look a bit ridiculous with a suit. As if you’re perpetually on your way to shovel out your snowed in Pontiac for the morning commute or you’re at one of the Duck Dynasty guys’ wedding. Not so with Alden’s Indy boot. Narrow, with a lower, shoe-like profile and leather soles it epitomizes a country gentleman’s toe cover. Wolverine’s heritage line provides something just as handsome for about $100 less. Made in the USA using full grain calfskin, either one should be your tweed trousers’ go-to wing man this winter.

Previously in Dress Like a Millionaire: Winter Essentials.

Evan Widhu is a Men’s Wear Buyer in New York. In terms of sheer numbers he’d like to think he has a millionaire’s shoe collection, although most of them happen to be Vans that were purchased during the Bush administration.