Halloween Costumes for Gentlemen – Stylish & Spooky Menswear Outfits

Halloween is a widely celebrated holiday around the world–but here at the Gentleman’s Gazette, we’ve got multiple perspectives on its significance. Growing up in Germany, Halloween wasn’t really a big deal for our founder, Sven Raphael Schneider (although he did meet his wife, Teresa, at a Halloween party when they were both in school). Meanwhile, I grew up here in the United States and Halloween was a considerably bigger deal. I dressed up in various Halloween costumes over the years, often as superheroes because of my love of comic books, and I definitely enjoyed trick-or-treating and putting my costume together.

What we’ve come to realize is that there are a number of costumes that stylish gentlemen and appreciators of classic menswear can put together, either from items completely within their own closets, supplementing by going through a few vintage stores, or buying a few things online. We’re highlighting seven different costumes today and they all follow a specific set of criteria.

7 Classic Halloween Costumes for Men

The costumes we’ll discuss are all based in classic men’s style, and as I said, most of the core pieces will be able in your wardrobe if you already have an appreciation for classic menswear. Furthermore, we believe all of these costumes are classy or in good taste, not too makeup heavy, and instantly recognizable. When you walk into a room or a Halloween party, people will immediately know who or what you’re supposed to be.

1. Traditional Vampire/Count Dracula

Certainly, the vampire is one of the staples of Halloween costumes, right up there with things like witches or Frankenstein’s monster. Fortunately for the classic-menswear lover, you can pull off a traditional vampire costume using a white tie ensemble. Of course, there are many different variations for vampires, but we’re going with the look immortalized by actor Bela Lugosi in the 1931 film version. In addition to the white tie ensemble making up the core of your outfit, you’ll also want to supplement with two pieces that you could easily find online: a cape with a high collar and a medallion to be worn around the neck.

If you’d like, you could also supplement with a bit of makeup, like some white face powder or some blood at the corner of your mouth achieved with lipstick. However, neither of these things are absolutely essential. Also in that category would be some of those false plastic vampire teeth because they might just get in the way of your speaking and be generally inconvenient. If you don’t have a white tie ensemble to wear, you could also pull off a traditional vampire costume by using the cape and a black tie ensemble, or something even less formal like a black necktie, white shirt, and red vest. 

2. Indiana Jones

Next up is the famous film adventurer, Indiana Jones. Given that Indiana Jones’ costume was itself inspired by earlier film serials of the 1940s and films like Treasure of the Sierra Madre with Humphrey Bogart, there are definitely some classic style elements involved, most notably, the dark brown fedora that you’ll often see Indy wearing. In addition, you’ll need a brown leather jacket and ideally, also a small brown leather messenger bag.

Your shirt and trousers could be anything on the brown scale; you could wear something in khaki, or brown pants and a white button-down collared shirt that has a bit of a rumpled appearance to it. I’m wearing brown leather boots here, and an extra belt to simulate the gun belt that Indy wears. Cap off the look with a whip, and you’ll be ready to go on an adventure.

3. Phantom of the Opera

Another costume involving white tie is the Phantom of the Opera. This one’s fairly easy as well, as the white tie ensemble makes up the bulk of it (note, however, that most depictions of the Phantom onstage and in film tend toward using a black waistcoat). You’ll just need the Phantom’s half-mask for that instantly iconic look, and you could also wear a cloak, as well.

If you’ve got the core pieces of a white tie ensemble together but you’re looking for some high-quality white-tie accessories, you don’t have to look any further than the Fort Belvedere shop; we offer a wide range of accessories to go with formal wear. And as with the vampire costume, if you don’t have white tie, you could probably get away with wearing black tie in a pinch, just so long as you remember that iconic half-mask.

4. Agent Smith/Secret Agent

Next up is a slightly more modern look: Agent Smith from the film The Matrix. You could also pass this off as a more generic “secret service” or “spy” costume as well. What you’ll need here is a black suit, black long necktie, and white shirt, in addition to other elements like black socks and shoes.

If you want to go for an Agent Smith costume to the tee, the specific design of sunglasses that Agent Smith wore in the film can be found online, as can an earpiece. I’m also supplementing here with a thin tie bar across my tie, and wearing my French cuff shirt with the cuffs undone inside the sleeves of the jacket. This was a particular style quirk that I picked up on when viewing the film again recently.

5. Charlie Chaplin’s “Tramp”

Our fifth costume is Charlie Chaplin’s famous “tramp” character. He would wear ill-fitting morning dress in this role to accentuate the clownishness of the character. As such, you’ll need a traditional morning wear ensemble of striped pants and a dark coat, as well as a shirt with a wing collar (or a turndown collar made to look like a wing collar in a pinch) and a dark tie. Capping off the look would be a bowler hat and cane to do some of the prop comedy that Chaplin was famous for.

You’ll also need some black eyeliner to draw in some eyebrows and the famous toothbrush mustache that Chaplin’s “tramp” character sported. You could, of course, go out and buy a false mustache to wear, but we wouldn’t recommend this for a few reasons. First of all, these kinds of toothbrush mustaches will more often be sold as Hitler mustaches than Chaplin mustaches. Second, the adhesive used to put these mustaches on can be uncomfortable, and may not hold throughout the course of the evening.

6. Clark Kent (Superman)

Pictured below is a Clark Kent costume mid-transformation to Superman. This one resonates for me, as it incorporates my love of both comic books and classic style (with the blue suit). Blue is the most traditional color for Clark Kent as seen in the comic books, but you could get away with really any suit color, as well as any shirt and tie. Most traditional here, though, would be a white shirt and a red striped tie as I’m wearing.

It will also help to slick back your hair and wear glasses–two things I already do naturally so this costume is even easier for me! You could supplement with a hat like the gray fedora I’m wearing here today (also most traditional). And of course, the key for this costume would be the Superman t-shirt worn underneath the dress shirt; that way, you can achieve a “mid-transformation” look.

7. Gordon Gekko

Our final costume today is another film character, Gordon Gekko from the film Wall Street. Here, you’re going to want to go for that distinctly “1980s-power-suit-corporate-raider” look, so you’ll want to slick your hair straight back and incorporate several features like suspenders and a Winchester shirt. Wear a bold, wide tie with a large pattern, and also, you could wear something like gray trousers with inward-facing pleats.

Supplement with a jacket if you’d like, or you could leave it off and show the suspenders and two-toned shirt. Add optional props like a cigar or maybe a 1980s style brick phone, and you’ll complete the Gordon Gekko look. Just remember that “greed is good!”

Conclusion

These seven costumes are just a sampling of some of the ideas we had. There were also a few others, but they were a bit more involved as to supplementary pieces. For example, you could look to something like Dick Tracy, which would require a yellow trench coat and fedora. Probably possible to find somewhere, but definitely more difficult than any of the options we listed here today. You could also try something like James Dean with his iconic red Harrington jacket from “Rebel Without a Cause.” Have fun assembling your costumes, and Happy Halloween!

If you’re aware of any other costumes that incorporate classic menswear, be sure to let us know in the comments below!