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The 7 Pairs of Dress Shoes Hollywood's Top Stylists Think Every Man Should Own

Saturday, September 10, 2016
  • The simple black, lace-up got a vote from every stylist we polled. An oxford is a classic choice, just be sure to go for a cap- or plain-toe style. A wholecut oxford is a beautiful shoe but too dressy to be a real workhorse in your wardrobe. “If you can only afford one, a beautiful black lace-up dress shoe is always one to invest in. It’ll work with almost every suit you own—even a tuxedo.” —Samantha McMillen Church's Polished Leather Oxfords, $650, available at mrporter.com

Black Oxfords

The simple black, lace-up got a vote from every stylist we polled. An oxford is a classic choice, just be sure to go for a cap- or plain-toe style. A wholecut oxford is a beautiful shoe but too dressy to be a real workhorse in your wardrobe.

“If you can only afford one, a beautiful black lace-up dress shoe is always one to invest in. It’ll work with almost every suit you own—even a tuxedo.” —Samantha McMillen

Church's Polished Leather Oxfords, $650, available at mrporter.com

  • A dark brown perforated brogue or wingtip is a buy nearly every stylist mentioned in our survey. This go-to shoe is a slightly less dressy alternative to a black lace-up oxford and yet still the picture of class. “A brown lace-up wingtip with a round or pointier toe is an essential for every man. Once you’ve got that and a black oxford in your closet, you can start playing around more.”—Jeff K Kim Jack Erwin Wingtip Oxford, $195, available at jackerwin.com

Brown Brogues or Wingtips

A dark brown perforated brogue or wingtip is a buy nearly every stylist mentioned in our survey. This go-to shoe is a slightly less dressy alternative to a black lace-up oxford and yet still the picture of class.

“A brown lace-up wingtip with a round or pointier toe is an essential for every man. Once you’ve got that and a black oxford in your closet, you can start playing around more.”—Jeff K Kim

Jack Erwin Wingtip Oxford, $195, available at jackerwin.com

  • Most of the stylists we polled put at least one suit-friendly boot on their must-own list. While chukkas, moto boots, and desert boots were all mentioned, the Chelsea boot won the most votes. “I love Chelsea boots because you can wear them with a sweater and fitted denim for a night out and then turn around and wear them to the office with a suit and tie. No one makes a better Chelsea boot than Tom Ford”. —Avo Yermagyan Tom Ford Gianni Chelsea Boot, $1,990, available at tomford.com

Chelsea Boots

Most of the stylists we polled put at least one suit-friendly boot on their must-own list. While chukkas, moto boots, and desert boots were all mentioned, the Chelsea boot won the most votes.

“I love Chelsea boots because you can wear them with a sweater and fitted denim for a night out and then turn around and wear them to the office with a suit and tie. No one makes a better Chelsea boot than Tom Ford”. —Avo Yermagyan

Tom Ford Gianni Chelsea Boot, $1,990, available at tomford.com

  • A double or single monk-strap shoe will instantly give your suits and dressier clothes some European charm. While most stylists we polled didn’t put it at the very top of their list, many mentioned it was a good second or third buy. “Johnston & Murphy makes the most comfortable (and most affordable) shoe on the market and I love their new monk straps. My guys put them on and they never want to wear any other shoe brand ever again—you’ve just got to get the right styles.” —Ilaria Urbinati Johnston & Murphy Nolen Monk Straps, $185, available at zappos.com

Monk Straps

A double or single monk-strap shoe will instantly give your suits and dressier clothes some European charm. While most stylists we polled didn’t put it at the very top of their list, many mentioned it was a good second or third buy.

“Johnston & Murphy makes the most comfortable (and most affordable) shoe on the market and I love their new monk straps. My guys put them on and they never want to wear any other shoe brand ever again—you’ve just got to get the right styles.” —Ilaria Urbinati

Johnston & Murphy Nolen Monk Straps, $185, available at zappos.com

  • Speaking of old-world charm, it doesn’t get any swankier than a dressy leather, suede, or velvet loafer. If you’re starting to really get into formalwear, or you happen to be a movie star's stylist, these shoes will soon land on your shopping list. “For spring and summer formal occasions, we love Christian Louboutin’s gorgeous Dandelion loafer. They’re elegant without being too flashy.” —Wendi and Nicole Ferreira Christian Louboutin Dandelion Flats, $895, available at us.christianlouboutin.com

Elegant Loafer

Speaking of old-world charm, it doesn’t get any swankier than a dressy leather, suede, or velvet loafer. If you’re starting to really get into formalwear, or you happen to be a movie star's stylist, these shoes will soon land on your shopping list.

“For spring and summer formal occasions, we love Christian Louboutin’s gorgeous Dandelion loafer. They’re elegant without being too flashy.” —Wendi and Nicole Ferreira

Christian Louboutin Dandelion Flats, $895, available at us.christianlouboutin.com

  • Whether it’s a suede derby shoe or a twist on that idea, a dress shoe that’s one step down in formality from a wingtip, but still works with a suit, is a smart buy for summer weddings or more casual days at the office. “Once you own a black lace-up shoe, I think a light-color suede or caramel leather shoe is nice to have on hand. They’ll look great with your lighter summer suits.”—Samantha McMillen Officine Creative Princeton Derby Shoe, $615, available at mrporter.com

Suede Derby Shoes

Whether it’s a suede derby shoe or a twist on that idea, a dress shoe that’s one step down in formality from a wingtip, but still works with a suit, is a smart buy for summer weddings or more casual days at the office.

“Once you own a black lace-up shoe, I think a light-color suede or caramel leather shoe is nice to have on hand. They’ll look great with your lighter summer suits.”—Samantha McMillen

Officine Creative Princeton Derby Shoe, $615, available at mrporter.com

  • Here’s a must-own dress shoe that wouldn’t have been on the list a mere decade ago: the no-fuss, premium leather sneaker. Many stylists mentioned this as a young-guy essential, citing Common Projects and Axel Arigato as favorite brands. “The leather sneaker has become a big must-have in Hollywood and elsewhere. It can be worn for casual occasions with jeans or to cocktail-attire parties with a nice suit.” —Jeanne Yang Axel Arigato Clean 90 Sneaker, $225, available at axelarigato.com

Spare Leather Sneaker

Here’s a must-own dress shoe that wouldn’t have been on the list a mere decade ago: the no-fuss, premium leather sneaker. Many stylists mentioned this as a young-guy essential, citing Common Projects and Axel Arigato as favorite brands.

“The leather sneaker has become a big must-have in Hollywood and elsewhere. It can be worn for casual occasions with jeans or to cocktail-attire parties with a nice suit.” —Jeanne Yang

Axel Arigato Clean 90 Sneaker, $225, available at axelarigato.com



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