Dec. 13, 2013 4:37 p.m. ET  Photo Details (front to back): Oxford, $345, allenedmonds.com; Freemans Sporting Club by Allen Edmonds Saddle Shoe, $484, Freemans Sporting Club, 212-673-3209; Loafer, $595, tods.com; Church's Shoe, $735, leffot.com; Bluchers, $298, jcrew.com; Derby, $1,710, John Lobb, 212-888-9797; Brooks Brothers Peal & Co. Shoe, $648, brooksbrothers.com; Monk Strap, $550, Bally, 212-751-9082; Derby, $1,250, Hermès, 800-441-4488; Shoe, $598, brooksbrothers.com; Derby, $265, walkover.com; Loafer, $548, Paul Stuart, 212-682-0320; Oxford, $695, Canali, 212-752-3131; Oxford, $198, colehaan.com; Boot, $248, jcrew.com; Boot, $525, Crockett & Jones, 212-582-3800; Boot, $870, Hermès, 800-441-4488; Boot, $395, allenedmonds.com; O'Keeffe Boot, $975, mrporter.com  FORMER BANKER Paul Grangaard recalls a time when most of his colleagues owned only a few pairs of shoes: two to alternate between for work, one for the weekend and a pair of running shoes or sandals. That, he has noticed recently, is no longer the case.  "I have a friend who's the CEO of a Fortune 500 company in Minnesota. He tells me this is the first time he's had more than four pairs of shoes," said Mr. Grangaard, 55, now the president and CEO of American shoe brand Allen Edmonds. "He said he's up to seven, and it's all my fault."  When it comes to footwear, men's attitudes are starting to resemble those stereotypically associated with women. The signs are everywhere. Over the last year, J.Crew doubled its men's dress shoe offerings. Saks Fifth Avenue has been devoting more and more space to men's shoes; in its Beverly Hills menswear store, footwear now occupies the entire first floor. Since Mr. Grangaard took over at Allen Edmonds in 2008, he's doubled the company's business by reviving classic styles along with more contemporary spins on them.  "There is an explosion of men's shoes right now. The business is on fire," confirmed Eric Jennings, Saks Fifth Avenue's vice president and men's fashion director. "It runs the gamut from classic dress shoes to designer sneakers that are extremely fashion forward."  So which pairs does a guy now need to own? Mr. Jennings's list of essentials includes wingtip brogues, cap-toed lace-ups, slip-on loafers and any style in cordovan-hued leather, which coordinates well with blacks, blues and browns. A monk-strap shoe, he added, while not essential, can be a smart addition.  "I've got derbies, bucks, wingtips, brogues and a monk -strap," said Andrew Chisholm, a 34-year-old New York-based advertising copywriter who has signed up for a shoemaking course at the Fashion Institute of Technology. The side-buckled monk-strap style happens to be a favorite of J.Crew's head of men's design, Frank Muytjens, who showed both suits and jeans from his spring collection on models wearing white or gray suede double-strap monks from English brand Alfred Sargent.  Sam Lobban, senior buyer for online retailer Mr Porter, adds boots to the list, whether Chelsea, desert or chukka. None of these above styles is particularly new; in fact, they're classics. What makes the current offerings a footwear feast is the sheer volume of new colors and fabrications as well as subtle tweaks to familiar shapes.  Some also consider a new popular category—the fashion sneaker—to be an essential. High-end fashion brands like Lanvin, Balmain and Saint Laurent are finding an ever-growing market for their versions, which start around $500 and go up to four figures. "It used to be 'Sex and the City,' women and the Manolo Blahnik. Now it's men spending $1,000 on sneakers," said Matthew Chevallard, the 27-year-old co-founder of Del Toro, a contemporary shoe brand he founded in 2005.  One man instrumental in establishing the sneaker trend is Prathan Poopat, 41, the co-founder of Common Projects, a line of minimalist kicks that have married running shoes to Italian leather and shoemaking since 2004. "It seemed like a gap in the market," said Mr. Poopat. "Something very basic, something luxury that wasn't screaming a logo or a brand." Such innovations blurred the line between casual and dress-up. Suddenly, there was a pair of sneakers that you could wear to a dinner party. "For me, it's a wardrobe staple," said Lanvin menswear designer Lucas Ossendrijver, who added sneakers to the tailoring-centric French label. Though Lanvin has introduced more athletic-looking cross-trainers and high-tops, the cap-toed sneaker Mr. Ossendrijver first made—think a fancy pair of Converse—continues to be the best-seller.  One can trace the shoe boom to a growing interest in menswear driven, in large part, by blogs and their endless streams of street-style photographs. As dress codes have relaxed and been reshaped (Mr. Jennings pointed out that shorter pant hems have shone more of a spotlight on shoes), men have started to use footwear to express their personal style. "You can see trends from all over the world—cool guys in Austin and Paris and Tokyo," said Los Angeles-based designer George Esquivel, 43, who began his career making shoes for members of Pearl Jam and Nine Inch Nails, and is now known for creating inventive custom shoes for fashion-forward clients like New York Knicks center Tyson Chandler. "Men start getting tired of black and brown and very basic things," Mr. Esquivel added.  As the shoe-niverse expands, a host of new brands and designers has emerged (see below). Perhaps the most prominent among them is Mark McNairy, 52, whose inability to find a proper buck five years ago led him to make his own. Since then he's applied a rainbow of colors both to the suede uppers and sometimes to the soles. "Mark has had a great influence on [the trend toward] merging street style with sartorial style," said Saks's Mr. Jennings. Del Toro's Mr. Chevallard gives classic smoking slippers a similar twist, offering them in plain black velvet or camouflage with a red toe cap.  Of course, many shoe enthusiasts still worship at the altar of tradition, coveting decades-old, UK-based brands in particular. "The demand for British men's shoes has gone through the roof," said George Glasgow, 30, who runs George Cleverley, a mostly custom shoe business his father opened in London in 1958. Since 2007, Mr. Glasgow has noticed a younger, savvier audience for his made-to-measure wares and for the ready-made shoes he sells through Mr Porter, where they are a top seller. "Ten years ago, it was the Duke of Beaufort," said Mr. Glasgow. Now it's younger bankers, guys in their 20s (guess where Daniel "Harry Potter" Radcliffe gets shod?) and even well-heeled university students (a pair of ready-made Cleverley oxford brogues costs $1,600). Younger customers are also buying driving loafers and refreshed neon-soled bucks and chukkas from American brand Cole Haan, founded in the 1920s.  In some cases, the two sides have merged in traditional-contemporary collaborations—114-year-old British company Alfred Sargent and J.Crew; Allen Edmonds and Freemans Sporting Club; 147-year-old brand Grenson and Rag & Bone—that provide the best of both worlds.  Menswear will never be a rule-free category, but the unprecedented number of footwear options has certainly broadened the scope of what's acceptable. Reflecting on how much codes have shifted, Allen Edmonds's Mr. Grangaard said: "When I went to work for an investment bank in 1986, our boss said he would never hire anyone who would wear brown shoes to an interview."  These three footwear brands, all recently launched, are making strides  New York-based designer Noah Waxman makes shoes that are Dutch-inspired but American-made. "Style in Holland is a perfect marriage between things that are cool and wacky [and the] very functional," said Mr. Waxman, who studied shoemaking in Utrecht in the Netherlands. The designer, 39, launched his eponymous footwear collection earlier this year. For fall, he updated the classic chukka-boot design with two unexpected materials—embossed Western leather and haircalf, both in a rich burgundy. For spring, he used raffia, a material not commonly found in men's footwear, with brightly colored suede. The line, he said, is for men who demand the sort of form and function that doesn't compromise style. "That's essential in shoemaking," he said. "It has to work in a technical sense, and be beautiful."  What do surfers and skateboarders wear when they graduate to the next phases of life? That's the question that Jim Leatherman, 33, and Josh Johnson, 32—both action-sports aficionados—pondered before launching their California-based footwear brand, Broken Homme, in 2012.  "We were thinking about the man who wasn't wearing Vans any more," said Mr. Leatherman. Forming the heart of the collection is footwear in traditional silhouettes that is sturdy enough to work in but sleek enough for formal affairs. The duo uses heavy black Vibram outsoles instead of leather soles in their boots and oxfords to avoid a too-formal look. They source full-grain hides from American tanneries in the Midwest and Southwest for a robust but polished feel. Broken Homme's shoes are completely made in the U.S.A., a point of pride for the designers. "We're not a heritage brand that's been around for a hundred years but we are conscious of being locally made," Mr. Leatherman said. "We consider ourselves a new generation of American craftsmanship."  "Feit is a play on the word 'fight,'" said Tull Price, 37, about the new footwear label that he and his brother, Josh, 34, launched in their native Australia. "It refers to the struggle of doing something you're passionate about." That could explain why the Prices only produce limited runs of each Feit style annually. Their process is painstaking: Every pair of their minimalist leather hiking boots, slippers and sneakers is hand-sewn from a single piece of leather that's fruit- and vegetable-dyed, then sits in a lightly steamed room for up to 10 days until the humidity naturally tightens the leather around the last—the foot-shaped form used by shoemakers—to create a superior fit. Now in its sixth season, Feit was picked up by the soon-to-open Dover Street Market in New York. And the Price brothers intend to remain in high-end boutiques. "We're not looking to build the business really big," said Tull. "We are focused on creating high-quality products on a small scale."
With the surge in men's footwear options, both style-conservatives and risk-takers are spoiled for choice (and perhaps a bit overwhelmed by it). Here, a guide to sole survival.