Dressing Like the Wolf on Wall Street

If there’s one thing that everybody can agree on it’s that Leonardo DiCaprio looks great in a suit. Even when it’s an antique suit (like the kind he wore in Django Unchained), he looks good. His new flick, The Wolf on Wall Street is no exception…in spite of the fact that he’s wearing a suit from the 80s with shoulder pads so big he looks like Michael Keaton at the end of Beetlejuice (after the witch doctor shrinks his head).


In spite of the regrettable fashion that the Wolf of Wall Street insists on making us remember, there are lessons to be taken from the movie. Here are some tips on how to look like a power broker in today’s market by taking what you see on screen and, for lack of better phrase, turning it on its ear:

The Suit
Just Say NO to shoulder pads. Well… at least say NO to the super puffy shoulder pads that make you look like you’re four and have stuffed your shirt with hand towels to look more like the football players you see on TV. A small, thin shoulder pad is okay—it gives your shoulders definition (if you’re insecure about a rounded shoulder) but, really, it’s best to eschew them altogether.

Just Say YES to pinstripes. Pinstripes never go out of style. The great thing about the pinstripes in Wolf’s suits is that they are spaced far apart, which helps cut down on the accidental zebra impersonation. And remember: light stripes on dark backgrounds. Never the other way around.

The Shirt
Picking a dress shirt can be tricky. When in doubt, go with white, light blue or light gray. Veeeeeery light pink (the closer it gets to salmon, the more it needs to stay in the store) can also pass.
Sometimes you can get away with a deeper color like a dark red, but use sparingly. Stick to the basics and don’t forget to wear an undershirt!

The Shoes
There are lots of choices when it comes to men’s dress shoes now. Obviously, you don’t wear brown shoes with a black suit. Laces can be okay, but only if they are short, thin and the shoe only requires short laces (think of them as accent pieces and not something that the shoe requires to stay on your foot).

The Tie
In the movie, you’ll see lots of wide neckties with big patterns. It was, after all, the 80s. Today, you’ll want something slimmer with a subtle pattern. You’ll want bold or subdued colors but not pastels. You definitely don’t want your tie to look like it’s been dipped in a bucket of water colors.

If you really want to dress up, you might want to take note of the fact that bow ties are making a huge comeback (thank Dr. Who). Silk bow ties for men are available all over the place and are a great way to add a touch of personality to your suit while still dressing up for both work and evenings on the town.

Bling is out, friends. Today it’s about subtle and well crafted garments. Shiny watch faces with leather bands are in. Huge gold watches are out. Pocket squares are in. Ascots are out (no matter what Tom wears on Parks and Rec). Rings are acceptable if you are married. You want to look snazzy and draw peoples’ eyes to a few important touches. You don’t want them to not know where to look first.

Do you like dressing like a Wall Street Shark? What’s your secret?