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How to Shop for Shoes Online

Score Ferragamo-quality kicks at Cole Haan prices.

When the designer Hardy Amies, one of the true menswear icons of the 20th century, remarked, “It is totally impossible to be well-dressed in cheap shoes,” he wasn’t wrong. After all, for eons really great premium-leather dress shoes—those spit-shined oxfords, loafers, or brogues you wear for job interviews and first dates—have been as much an investment as they are fashion pieces. But more and more lately, as online companies from Warby Parker to Bonobos continue to drive down prices on traditionally high-end goods by cutting out middlemen, we’re seeing a truly remarkable fashion first: Ferragamo-quality kicks at Cole Haan prices.

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Now, before you whip out your Amex card and start scouring the Web, know that shopping for shoes online requires a basic understanding of cobbling. For that, I tapped two experts: Sue Saunders, from the London College of Fashion’s cordwainers course, the world’s top shoemaking school, and Australian shoe designer Sebastian Tarek. Both of these shoe gurus emphasized over and over that when you’re shopping for new “affordable” shoes, regardless of style or brand, leather quality is paramount.

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According to them, shoe leather is graded from A to C. You want to steer clear of the cheapest skins—and trust me, there are a lot of C-grade shoes sold online. So ask a company’s customer service about the grade directly. If they don’t know or won’t tell you, activate that zoom view on the website: If you see a smooth, even surface on the leather where you should see the occasional hair dimple, it’s ersatz and embossed—do not buy. Also, study the area where the shoe and sole are joined. You should see clear evidence of stitching. When you’re reading the write-ups, look for key terms like “Goodyear-welted” or “blake-stitched,” which are age-old cobbler techniques that indicate a lasting quality.

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Finally: the fit. Your best indication of comfort is the provenance, so scan the label. If you have wider feet, look for shoes from Italian or Brazilian factories, which tend to offer softer and lighter styles. If you have longer, more slender feet, try Spanish shoes, which are stiffer and narrower. (If you’re buying American: Sorry, dude, the fit’s all over the place.)
And though Amies would have told you that dress shoes are entirely about style, not comfort—and definitely not about physical health—we beg to differ. “A slightly higher heel is better for posture and spinal alignment, and it’s more comfortable,” says Saunders. Ideally, you should aim for around an inch, even a little higher, she explains. So bear that in mind when you’re cruising these companies’ websites. I did.

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Here are my personal favorite high-end shoe brands you’ve never heard of.

For: A Job Interview

Brand: Jack Erwin (
Price: Most styles About $200

This brand-new shoe company, which specializes in classy wingtips and brogue boots, was founded by two buddies in New York who couldn’t find great shoes for a wedding. (This company is so brand-new, in fact, that its Soho office doubles as home for its founders, Lane Gerson and Ariel Nelson). But their shoes are superbly well-crafted in Spain from Italian and French calfskin leather and are blake- or Goodyear-stitched. The styles are classic and unfussy—my favorite is the Joe ($195), a preppy cap-toe that pairs well with suits and jeans. Bonus: Erwin offers gratis shipping and returns, so you can assess pairs for free, or just stop in the fitting room at its new retail space in NYC.

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For: A Hot Date

Brand: Paul Drish (
Price: Most styles $250-$275

No doubt the most fashion-forward of the group, Paul Drish is the brainchild of Arveena Ahluwalia, whose family has been making shoes in India for other brands for more than 25 years and who created the label after spotting the potential in selling direct to consumers. The shoes are made from A-grade leather, and all shipping is free; there’s even a $20 credit on your first return toward a new pair of shoes. The line also launched its own “Accu Foot Size” smartphone app, which helps you size your foot in just minutes. The only issue: There are some clear missteps in the huge collection, notably some of the more decorative styles, so stick with the simpler versions, which aren’t quite as edgy and pointy-toed, and you can wear them both Friday night and Monday morning.

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For: Hitting The Bars With Buddies

Brand: Sarosso (
Price: From $170; Custom Shoes from $270

Founded by two European MBAs, Scarosso heavily touts its Italian manufacturing and premium calf leather from Tuscany. The designs are sophisticated, and you can customize every detail of a made-to-order pair, NikeiD-style, from color to decoration. Unfortunately, the European firm’s cobbling biz is hobbled by import-related red tape stateside: Even if returns are free, you can rack up costs just to sample the product. Regardless, these are must-have shoes.

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For: Guys Who Usually Wear Toms

Brand: Nisolo (
Price: From $144

Nisolo hails from northern Peru, where, until recent years, traditional shoemakers struggled to adapt to the modern market. Not anymore. Nisolo, co-founded by Patrick Woodyard and Zoe Cleary, employs more than 40 people full time to make its range of shoes and boots, specializing in more casual styles like the chukka or desert boot. Unfortunately, the soles are welted without Goodyear construction, which somewhat undermines their durability. But these are the cheapest of the bunch, and solid shoes. Plus, Nisolo offers free returns, exchanges, and full refunds to boot.

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