Opulent October Halloween Costumes

Halloween is less than a week away, and if you haven’t put together your costume or decided what you’re gonna wear, fear not, for we have your back. Here’s a list of costumes you can put together at Wingtip–or perhaps from your own well-equipped closet.


Steve Jobs

Another Steve Jobs movie in the theaters gives you license to cakewalk through another Halloween. Relatively simple, all you need is a black turtleneck sweater, a pair of jeans, and some dad sneakers. You probably have the phone already, too. (Wingtip turtleneck by Johnstons Of Elgin $425, jeans by Agave)

Magic Mike

If you’re in shape and you don’t mind freezing your ass off for the evening, then this might be the perfect costume for you. The bare essentials for this look are basically a pair of jeans…and a belt. If you want to get a little saucy, you can add a piece of flair such as a hat, or a tie, or even a bandana around the neck. (Jeans by Agave, Belt by W. Kleinberg, bandanna by Dunhill)

Richard From “Silicon Valley”

This costume literally takes no effort whatsoever. You can put this look together with a medley of things in your closet. Shirt? Check. Sweater? Check. Pants? Check. Boom, you’re done.(For the hoodie, try this new one from Peter Millar or the deluxe cashmere version from Derek Rose, pictured above. For the shirt, try this new Foster Plaid from Bills Khakis.

Uncle Buck

John Candy’s cult character is an oldie, but a goodie. So easy even a freaky pumpkin could pull it off. (See above.) All you need is a medium brimmed hat, a gray scarf, and a drill or hatchet for all-purpose menacing. It also helps if you have a cigar or tumbler of booze. Gee, where could you get those things? (Hat by Goorin Bros and Scarf by Johnston of Elgin. Stop by the store if you need a stick and a dram.)

Don Draper On Vacation

“Mad Men” is no longer on the air, but that doesn’t mean its spirit is gone. There will be reruns, and the show is still relevant enough that you can dress up and not get weird looks. We chose the Don On Vacay look (Khakis by Bill’s Khakis $145-$150, Button down Oxford shirt by Wingtip $150) as an option for everyone who’s already used the Don Draper In A Suit look. Which brings us to…

Anyone suited…ever

If you’re super lazy, like me, or you just want an excuse to buy a new suit, then you can just put on said suit and be anyone you want to be, providing you have the right accents. Here are a few examples:

This year I’m going as Agent Coulson. (Top-left.)


Pumpkin illustration by Scott Carl
Be Sociable, Share!

Tim Niven

Tim is Wingtip's Assistant Product Manager, a Bay Area native who has been with the company since 2013. Tim's a connoisseur of film and television, and by that he means he Wikis plots for film and television. His style inspirations come from the little screen--Barney Stinson, Brad Williams, and Tom Haverford. He is also a huge comedy nerd, as well as a regular nerd. He is an avid wearer of suits.

Submit a comment

Your email address will not be published. Required fields are marked *