The Wolf of Wall Street: Dark Blue Chalkstripe Flannel on IPO Day

Leonardo DiCaprio as Jordan Belfort in The Wolf of Wall Street (2013).

Leonardo DiCaprio as Jordan Belfort in The Wolf of Wall Street (2013).


Leonardo DiCaprio as Jordan Belfort, shrewd Wall Street stockbroker

Long Island, Fall 1993

Film: The Wolf of Wall Street
Release Date: December 25, 2013
Director: Martin Scorsese
Costume Designer: Sandy Powell
Tailor: Leonard Logsdail


It’s Labor Day, so sartorial traditionalists should start packing up their cream linen suits and pull their sharp chalkstripe flannels up to the front. Ideally, you have today off of work and one extra day before you need a snazzy suit to make an impression when strutting back into the office tomorrow.

Though avoiding excess isn’t exactly Jordan Belfort’s thing (i.e., drugs, women) in The Wolf of Wall Street, he did manage to avoid some of the sartorial excesses of the late ’80s and early ’90s that continue to plague thrift shops and convenience stores to this day. For the most part, he avoids baggy double-breasted suits with low button stances and excessive shoulder padding.

Although some of his fashion choices earlier in the film are regrettable—albeit very fitting for a young stockbroker trying to make it in 1987—he pins down a solid look later as his career matures, wearing a series of blue and gray power suits in a variety of fabrics and patterns.

What’d He Wear?

One of my favorite suits from The Wolf of Wall Street is the dark blue chalkstripe flannel suit that Belfort wears for the Steve Madden IPO, tailored for the production by Leonard Logsdail.

Steve Madden doesn't quite share Jordan's sartorial panache.

Steve Madden doesn’t quite share Jordan’s sartorial panache.

This suit was so indicative of Belfort’s success that Scorsese opened the film with Jordan wearing it during his fourth wall opening monologue. Jordan walks down the stairs of his sprawling Long Island mansion and steps outside, the sharp blue suit providing a rich contrast against the fall colors around him.


Morphine, anyone?

The jacket is single-breasted with peak lapels that are wide enough to look luxurious without being excessive. It buttons perfectly around the navel, unlike the popular but ultimately shitty extra-low stance of the era. Jordan typically keeps his top button fastened.

Belfort’s jacket has a welted breast pocket, flapped hip pockets, and 4-button cuffs. The shoulders are only slightly padded – another respite from the nearly bulletproof padding in most ’90s power suits – with roped sleeveheads. Edge stitching is present throughout, especially on the lapels.

As Jordan addresses his troops, his drug-fueled energy often sends him into a frenzy and the double rear vents flap up to reveal a subtle burgundy silk lining inside the jacket.

Jacket AND pants.

Jordan’s office and comically bulky computer monitor. Remember when computers weighed more than 8 pounds?

The suit trousers also avoid some of the shittier ’90s styling with a slightly low rise, belt loops, and double forward pleats. The trousers definitely have slanted side pockets, but there appears to be no left rear pocket. The cuffed bottoms fall with a medium break over his feet.

Speaking of his feet, Belfort wears a pair of black leather cap-toe balmorals with black dress socks. The black leather shoes nicely match his black leather belt. A flashier dresser would have likely opted for a pair of brown shoes with suspenders rather than a belt, but Jordan knows when he has to tone things down for business.


Wearing a striped shirt with a pinstripe suit is not a cautious man’s game. It can often look clashy, clownish, and ultimately stupid. Some men say to avoid it altogether. However, Jordan goes at it with a sense of sartorial intelligence that would be difficult to copy. His shirt is pale blue with darker blue stripes of alternating width. At a distance, it all softens to a solid light blue, and up close it adds a sense of sophistication and refinement. Neither the stripes of the suit or the shirt are too bold to out-do the other; both striped garments actually complement each other.


Note that I said they “complement” each other, not “compliment.” Jordan’s shirt is not telling his suit that it played a great game of golf last night.

The striped cotton shirt has substantial collars with a moderate spread. It buttons down a front placket, and has French cuffs that Jordan fastens together with mother-of-pearl links on a silver base. It fits across the rear with a plain yoke and side darts.


Jordan enjoys his morning routine of drugs and OJ.

The most eye-popping part of Jordan’s attire is his dark red silk tie, littered with white polka dots. Some men – the unadventurous type totally afraid of wearing striped shirts with striped suits – also forbid patterned ties on patterned shirts, likely out of fear of appearing like this. Jordan, of course, boldly says “fuck you” to this mindset (as he is wont to say to so many things!) and wears this equally bold tie.


…but he also burns dollar bills and does cocaine off of his desk, so let’s not start getting too many tips from this guy.

Jordan doesn’t accessorize much. Other than his cuff links, he only wears a watch and his wedding band, which is a plain gold band worn on his left ring finger. He may not honor the marriage very well, but at least he wears his ring?

Ring and watch.

He sat down.

His favorite accessory is obviously the “gold fuckin’ watch” that he tosses out into the crowd. When I first saw the film, I assumed it was a Rolex—possibly a GMT Master or a Submariner. Of course, both rewatching the film and scanning Internet proved me wrong, and it was revealed to be a TAG Heuer Series 1000, described by The Gentleman’s Journal as:

…an iconic gold divers sports watch from the mid 1980’s, which was phased out in the early 1992. A real icon of it’s generation, the series 1000 was unusual as not many people found the solid gold watch appropriate for diving. But in our opinion it is perfectly fitting for an outrageously badly behaved stock broker such as Jordan Belfort, to whom symbolizing wealth, power and extravagance is a daily routine!

Jordan's "gold fuckin' watch" never has a typical day at the office either.

Jordan’s “gold fuckin’ watch” never has a typical day at the office either.

Jordan does wear the watch in many of his earlier scenes at Stratton Oakmont, but he makes good on his word. Once he tosses it out into the crowd, it becomes the property of one lucky salesman. It fits snugly on his wrist, but he does unbuckle it when giving his speech (as one of the first screencaps on this post shows). In fact, while he gets up close and personal during the speech, his loosened watch even slips back over his shirt cuff.

Curious about what the real Jordan Belfort wore on Steve Madden IPO day? Belfort’s memoir The Wolf of Wall Street describes his attire on Wednesday, December 13, 1993 as a gray pinstripe suit, a blue tie with “little fishes” on it, black crocodile skin handmade cowboy boots (oh my…), and a thin, gold Bulgari watch that he describes as “understated” despite its cost of $18,000. I think this might be a case where fiction trumps reality. Advantage DiCaprio.

Go Big or Go Home

Despite his unsavory habits, there’s no denying that Jordan Belfort knows how to get his team of employees motivated. His confidence carries to his sales team via both his fashionable business attire and his borderline psychotic energy.

Jordan's already got his watch ready to toss.

Jordan Belfort is a much more pleasant type of “American psycho” that Patrick Bateman. Where Bateman got his jollies from torturing prostitutes, the more good-natured Belfort preferred to toss his expensive watch into his employees’ workspace as positive reinforcement to sell. This comparison should make Belfort a much more sympathetic protagonist.

Of course, it’s not made explicit how much of that confidence is the result of his drug intake…

On a daily basis, I consume enough drugs to sedate Manhattan, Long Island, and Queens for a month. I take Quaaludes ten to fifteen times a day for my “back pain”, Adderall to stay focused, Xanax to take the edge off, pot to mellow me out, cocaine to wake me back up again, and morphine… Well, because it’s awesome.

Jordan’s methods of self-medication may contain some relatively harmless stuff, but mixing it all together is not a good idea. To relate, it’s like my common practice of ordering a bacon cheeseburger. Yes, I enjoy it despite the associated health risks, but I don’t order every burger on the menu. (Then again, a Carl’s Jr. Texas BBQ Burger® doesn’t quite cancel out the effects of an Applebee’s Cowboy Burger®. Maybe I didn’t think this analogy through… Just don’t mix a lot of drugs, kids.)

How to Get the Look

Jordan Belfort commands his office both with his attitude and his attire. This stylish spin on the traditional power suit is one of the few aspects of his character that should be emulated in real life.


  • Dark blue chalkstripe flannel suit:
    • Single-breasted jacket with peak lapels, 2-button front, welted breast pocket, flapped hip pockets, 4-button cuffs, slightly padded shoulders with roped sleeveheads, and double rear vents
    • Double forward-pleated trousers with belt loops, slanted side pockets, and cuffed bottoms (“turn-ups”)
  • Light blue striped shirt with large collars, front placket, rear side darts, and double/French cuffs
  • Dark red polka dot silk tie
  • Mother-of-pearl rectangle cuff links with silver trim
  • Black leather belt with silver square clasp
  • Black leather cap-toe balmorals
  • Black dress socks
  • TAG Heuer Series 1000 yellow gold wristwatch with gold bracelet, black bezel, and black dial
  • Plain gold wedding band, worn on left ring finger

Double points to anyone whose clothes are custom tailored by Giorgio Armani himself… If so, I’m assuming you don’t need a blog to tell you what to wear.

Do Yourself a Favor and…

Check out the movie. And, you know, don’t mix a lot of drugs. Mixing burgers might be okay, I forget where we landed with that.

The Quote

Let me tell you something. There’s no nobility in poverty. I’ve been a poor man, and I’ve been a rich man. And I choose rich every fucking time.


  1. teeritz

    Great write-up, LS! I spotted Leo Di C’s watch early on and I too thought it was a Rolex until the “throwing it onto the floor” scene. “Hey, it’s a TAG 1000!”, I thought to myself. I bought the two-toned model of the same watch back in ’87. Served me very well until I switched to an Omega automatic.
    I found it odd that Belfort, in the movie, WASN’T wearing a gold Rolex, since the brand had, by that time, become a symbol of excess and/or ‘having arrived’. Then I remembered that Di Caprio is a TAG Heuer ambassador and it made perfect sense after that. Besides, it’s a much cooler watch than a thin, gold Bulgari.
    And thanks, by the way. I didn’t know the word ‘complement’ existed until ten minutes ago.

  2. JJ Koogamelloncamp

    Black socks? Are you sure about that? My assumption is that he would have worn navy blue socks to match the his trousers. Never match your socks to your shoes are you’ll nail the dreaded ‘booted’ look. I’m actually surprised you don’t share in this perspective as you seem very well versed in the other sartorial details and features. Would love to be proven otherwise of course! Cheers 🙂

  3. Pingback: The Wolf of Wall Street: White Polo for Yachting | BAMF Style
  4. Pingback: The Wolf of Wall Street: Glen Plaid Suit in London | BAMF Style
  5. Pingback: The Wolf of Wall Street: White Polo for Yachting » BAMF Style

Leave a Reply