Categories: Men's Shopping

Men's Shopping: Oak Street

Author: Danny McCullough

Oak Street is the extra-toney little brother of Michigan Avenue. The stores are a tad smaller, the surrounding area is a little quieter, and it can all be seen in a busy afternoon--but don't let that fool you. Brands from around the world vie for a coveted spot on the street that transitions away from the bustle of downtown and reflects the calmer residential neighborhoods in the north. Oak Street has offerings Michigan could only dream about, and the modern male benefits from the sibling rivalry between the two, since together they house most of the major names in the fashion industry. If you're in Chicago, you have to visit Michigan Avenue, and since you're seeing Michigan Avenue, you have to amble down Oak Street.

Designer Paradise 

The label run-down begins with quality Italian cobbling at Tod's. Known for their exquisitely comfortable hand-made shoes, in addition to belts and bags, they have a range of men's styles for every occasion. Like all quality footwear, the shoes actually conform to your hoof once you break them in, and with a classic, understated elegance, you'll find yourself wearing them as much as possible. Tod's isn't alone on the strip, though, because right down the street is French ultra-label Hermes, attacking men's dress from all angles, from boots to blazers. Like most stores on the strip, the men's section in Hermes isn't massive, but they showcase quality pieces and no filler. The slice of France widens, with label Yves Saint-Laurent offering a sampling of everything for your wardrobe, including sunglasses and velvet dress slippers.

Unique Boutiques 

Brand-names don't have a monopoly on this prime real-estate, though. Chicago's very own George Greene is a boutique that pampers men, offering hard-to-find designers outside of New York. They have pieces from their own line, as well as Thom Browne, Kiton and Yamamoto. While the upstairs contains work-wear, dress shirts and suits, the bottom section has casual clothes and garments to relax in. If finding a unique suit is your mission, Tessuti for Men is also worth a shop. A Chicago original also, Tessuti offers high-quality clothing, friendly service, and brands you simply can't get elsewhere. Free from gauche labels and flashiness, there's a classic appeal to these clothes, as well as the mindset of offering peerless pieces to customers.

A Taste of New York

Aside from the two Chicago-only boutiques, no single store encapsulates the area as well as Barney's New York. The trend-setting staple offers a sampling of clothing from a variety of popular men's labels, like Band of Outsiders, Psycho Bunny, Theory and Juicy Couture, in addition to having a large shoe selection that stretches across all tastes. If you have ten minutes to shop for clothes in your entire trip before you head back to Oshkosh, Wisconsin, this is the one place to stop.

One and Only

Having taken a nice break from the smaller, name-brand luxury stores, you have to toss yourself back into the fray by visiting Loro Piana. A melody of men's clothing awaits, as this textile company-turned-fashion icon has been hand selecting their fabrics for years. They're known not only for their specially-raised New Zealand sheep's wool, but their ultra-luxurious, truly unique Vicuna wool. Vicunas are cousins to the llama, and known for their precious wool, which has a history of being worn by Incan royalty and is supposed to be the pinnacle of warmth and comfort, with Loro Piana being the only retailer in the world that can legally harvest it. Being on top isn't cheap, however, as one Vicuna-lined piece of apparel can cost tens of thousands of dollars. It's worth it to stop by the store and feel the material, but committing to such a purchase is another story altogether. Even if Vicuna cloth isn't your forte, Loro Piana also has a wide selection of cashmere goods, with their traditional styling ensuring that their clothing will stay in style as long as you plan to wear it.

Contemporary Chic

Italian fashion pillar Prada also has a presence on Oak, with their building housing a glass elevator and displays as contemporary as their merchandise. And last but certainly not least is Jil Sander, a company whose fusion of form and function has taken it to new heights. Each piece shows just how much thought was put into its production, with features like fully double-sided jackets to keep you warmer and anatomically cut-sleeves to roll with your movements instead of slowing you down. At the end of the day, you have to move with your clothes on, and no other design house embraces this concept as much as they do.

If your wallet managed to survive in one piece, and the banks haven't foreclosed on your house, consider this a successful venture into the upper echelons of the fashion world. With designers and shopping like this in such proximity to the Magnificent Mile, who needs Madison Avenue or Rodeo Drive?

Check out places of interest near Men's Shopping: Oak Street:

An Original Penguin
901 N. Rush Street, Chicago, IL 60611

An Original Penguin by Munsingwear offers trendy fashions for men, women, and boys in prices to fit every budget. 

 

Haberdash
1350 N. Wells St., Chicago, IL 60610

Schedule a one-on-one fashion experience at this high-end men's fashion shop in Chicago's Old Town neighborhood.

 

House of Kahn Estate Jewelers
60 E. Walton St., Chicago, IL 60611

This Gold Coast jeweler trades in all types of high-end jewelry, from engagement rings to necklaces and antique jewelry. Visit their boutique studio set in one of the country's most densely populated shopping districts.



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