Dapper Dress-Up

Looks Inspired by Halloween Icons

Trick or treat! One of the best things about the season leading up to Hallow’s Eve (aside from the Jack-o-Lanterns and candy, of course) is the fun of dressing up and expressing some sides of yourself that don’t necessarily get a lot of time in the spotlight. Whether you’re going to use the holiday as a jumping o point for a radical change, or if you’re simply aiming to add some killer coolness to your wardrobe, we’ve got some of the coolest looks inspired by some of the most iconic Halloween costumes that you’ll find in NYC this year.


Perhaps one of the most iconic characters in musical theater history, the titular character in The Phantom of the Opera has also become a supremely popular choice for Halloween. He’s kind of a slam dunk for everyone, isn’t he? Tall, dark, handsome (as long as the mask stays on) and with a spellbinding dash of mystery. Perfect for such a holiday.

For a look inspired by this iconic character, slip into an impossibly great tux from Hugo Boss, the Stretch Virgin Wool model. The satin trim on the peaked lapels provide some drama, while the darts at the front and back of the jacket are there to accentuate your shoulders and taper your waist. Of course, we’re not going to suggest a mask, but it is important to note how that flash of white up top does add a fun focal point. In the spirit of tipping the hat to the phantom, slip on a pair of champagne Marion Sun shades from Brooklyn Spectacles.

INDIANA JONESSo maybe the dapper, buttoned-up look isn’t what you’re looking for this Halloween. Maybe you’rethe rugged type or perhaps you’re looking to embrace that side of your personality. Hallow’s Eve is all about exploration and expression, after all. Indiana Jones is the epitome of all things dangerously rugged, and the centerpiece of achieving his heroic ensemble is nding the perfect brown leather jacket.

Eddie Bauer’s Leather Journeyman Bomber Jacket looks exactly like something that Harrison Ford’s Dr. Jones would wear. Evoking the spirit of the American adventurer, this hefty, chocolate-brown leather piece is built to last a long time. A note about buying leather: any great leather jacket should actually improve with age. You’ll need some movable and sturdy khaki’s to go with it, right? J. Crew’s Broken-in chino pant in 770 straight fit (which actually is available in five different colors) is a streamlined, wayworn and updated version of what Indiana might wear while taking down the Nazis.

CLYDE BARROWFor our last Halloween-inspired look, we’re turning to American outlaw Clyde Chestnut Barrow, better known simply as “Clyde.” While the boxy angles of suits made in the 1930’s aren’t really on trend, the combination of a deep charcoal gray beneath a lighter plaid print is still a handsome way to go. He’s the personification of a well-dressed bad boy. Hugo Boss’s slim fit Plaid Virgin Wool Suit will get your iteration of Clyde started.

The subtle plaid is both vintage and contemporary at the same time. The mother-of-pearl buttons, a trademark for the Hugo Boss brand, do wonders to bring your elegance to the forefront. J. Crew’s Slim Thomas Mason® white button-down, along with the ash of color in Paul Smith’s Men’s Black ‘Feather’ Print Silk Pocket Square, will complete this extraordinary look. If you’re looking to go full tilt with Clyde, you’ll also need a sweet lid. Paul Smith’s Men’s Slate Grey Wool Hat will give you that suave gangster heat that’ll give you command over any room you enter.