Lifestyle Style

Men’s Halloween Costumes to Boost or Work With Your Wardrobe

I don't know about you, but I hate wasting money on shitty novelty items I'll never use again (50 bucks for a 70s dude costume?!). On the other hand, I love special events and holidays (including Halloween) that allow me to justify certain purchases. A new suit for the company Christmas party or a new pair of shoes for your brother's wedding could be just the nudge you need to invest in some quality pieces.

Don't squander this opportunity to elevate your wardrobe by blowing precious cash on chintzy, cheesy, poorly-made costumes you'll never use again!

Instead, take a look below at some costumes that will allow you to invest in wardrobe staples, use what you already have, and look like a total boss in the process. Cigarettes optional (you'll see what I mean).



If you don’t already own a tuxedo, now is a great time to invest in one. Suitsupply has the best suits and tuxedos for the money. Alternately, you could wear a dark suit you already own and instead put your money toward the only black shoe you'll ever need.  Wear your tuxedo or suit with a crisp white shirt, a black bow tie, and polished black dress shoes. For accessories, consider simple cuff links (if wearing a french cuff shirt), a white pocket square, and an understated time piece.  Just be sure your hair is spot on, you're clean shaven, and you work on your British accent. Bonus points for showing up to the party in an Aston Martin DB5.



Every man has wanted to dress like Gatsby at least once in his life.  Looking for an excuse to wear that light-colored spring/summer suit one last time?  Now you have it. If you still need a light-colored, light-weight suit for your wardrobe, try searching various retailers' end-of-season sales to score great deals on a cotton, linen, or light-weight wool suit.  While spectator shoes are great if you've got 'em, most practically, you can opt for a pair of light-colored suede shoes.  Hit up your local thrift store for a pale summer tie (gold and silver work, too).  Now all that's left is to go around calling everyone “old sport” all night.



All you need here is a fitted gray suit (Suitsupply to the rescue again), white shirt, slim stripped or solid tie, and a tube of Brylcreem to give your hair the look and smell of the 1960s. Accessorize with an appropriately dressed lady on your arm and an Old-Fashioned in your hand for the evening. And if you're not accustomed to drinking classic cocktails, you better start practicing now.  Put down the Bud Light and start drinking like a gentleman.



The splurge factor to this look is the leather jacket.  If you've had your eye on a sweet jacket, now is your moment to pull the trigger.  While black was a common color for leather jackets in the 1950s, don't hesitate to snap up a good-looking jacket in a rich brown if that's your preference.  Just add a white t-shirt, raw denim (cuffed at the bottom), and rugged boots from your closet and you're good to go.  Hair should be slicked up and back (for help with this, meet my friend Murray's Pomade).


If you have the physique, put on a beater, throw on some lived-in jeans, a thick leather belt, and some work boots.  Style your hair (you may actually need to use a blow dryer and hair spray for this task). Pick up a pair of claws and dog tags to complete the look.  Try not to spill everyone's drinks with those claws though.


The first rule of Fight Club – you do NOT talk about Fight Club.  But the ninth rule of Fight Club is that if you've got the abs for it, you have to go as Tyler Durden for Halloween.  Put on a pair of dark trousers from your closet, cuff 'em, and skip the shirt and shoes. Apply a little makeup for a black eye, small cuts, and drips of blood and dangle a cigarette from your lips. Feel free to drink cheap, shitty beer all night with this one.  You could also hit up a thrift store for a red pleather jacket and a giant-collar 70s shirt for a more covered-up approach (or if you're attending an outdoor party).

Alright gents, let me know in the comments below – have you ever used Halloween as an excuse to beef up your wardrobes?  What did you do?

You Might Also Like

No Comments

Leave a Reply

About Me

Casual Style 101

Free style guide