After taking a serious nose-dive throughout the 90s, the past 20 years have been something of a renaissance for men’s style.
And nowhere is this more evident than in the sharp and stylish movie and TV characters that have graced our (flatter, thinner and incredibly more hi-def) screens.
Characters like George Clooney’s Danny Ocean, Jon Hamm’s Don Draper, Gabriel Macht’s Harvey Specter and Ryan Gosling’s… uhhhh, whatever-his-name-was-in-Crazy-Stupid-Love (Jacob, I think?) have given us a whole new generation of style icons.
But even among this pantheon of sharp dressed men, Matthew Bomer’s gentleman thief from the USA show White Collar stands apart.
From 2009 to 2014, the Neal Caffrey wardrobe perfectly embodied the modern-classic look:
A seemingly never-ending supply of perfectly cut suits, sharp skinny ties, timeless casual wear and, the piece de resistance, that patented Neal Caffrey hat.
Of course, as a fictional character on a B-level network where style is often more important than the substance of the plot (I’m looking at you, Suits), he also had more than his fair share of luck.
I mean, hasn’t every ex con in America had the experience of charming an exorbitantly wealthy elderly woman immediately upon being released from prison?
And how convenient that she just so happens to have a closet full of her husband’s incredibly stylish old clothes—all of which fit him like a f*cking glove!?!
But I digress.
Regardless of how contrived the plot line around Caffrey’s wardrobe was, the clothes themselves were certainly sharp as hell.
And fortunately for those of us who don’t have wealthy benefactors or the skills of a master thief, his style can be recreated in the real world without breaking (or robbing) a bank.
In this post I’ll share the essential elements of the Neal Caffrey wardrobe, explain how you can recreate his style in real life, and show you where to get the key pieces you’ll need to mimic his modern-classic look.
How to Dress Like Neal Caffrey
The Ultimate Guide to Neal Caffrey Style
First Up:
The Essential Elements of Neal Caffrey Style
The Three Piece Suit
Number one with a bullet.
Neal didn’t always wear a three-piece, but he opted for a waistcoat so often that the style has undoubtedly become his signature look.
Neal usually opted for dark, classically masculine colors like grey and navy, but also dabbled in brighter shades of blue and even green.
Again I say – based on the in-story explanation, we are meant to believe that he found these suits in a closet.
As with so many things about the show’s plot, it’s best not to think about it.
If you’re thinking about following Neal’s lead and picking up a three-piece for yourself, I highly recommend opting for either navy or a medium grey.
Both are extremely versatile, can be worn in almost any situation, and will never go out of style.
Of course, color is only one consideration. Check out my post about how to buy your first suit for a full break down of the others.
Below are a few sharp, slim-fitting options that definitely evoke Neal’s dapper look.
The Neal Caffrey Tie
Though they existed in different TV universes, Neal owes a debt of gratitude to Don Draper when it comes to neckwear.
White Collar debuted two years after Mad Men propelled the “skinny tie” craze into the popular conscience, which explains why the Neal Caffrey tie looks a lot like the Don Draper tie.
Neal almost exclusively wore thin ties that would have looked just as good in the 1960s as they did in the mid-2000s.
(That should say everything you need to know about how timeless this look is.)
One word of advice:
Remember that the width of your tie should be in proportion to the width of your jacket’s lapels.
If your jacket had wide lapels, a skinny tie will look weak, like it’s being over-powered from the outside.
And if your jacket’s lapels are relatively thin, a wide tie will look like it’s trying to burst out of your shirt.
Neal’s slim fit suits went perfectly with his skinny ties, so be sure to follow his lead and keep your ties to no wider than 2.5 inches.
Below are a few classic options that would make him proud.
Dress Shoes
(and Occasionally, Dress Boots)
I like to say that shoes are the secret weapon of men’s style, a truism that Neal Caffrey knew all too well.
While Neal’s shoes were no doubt exorbitantly expensive, yours don’t have to be.
The number one thing that distinguishes a “decent shoe” from a “Neal Caffrey shoe” is the toe shape.
I’ve written about toe shape elsewhere so I won’t go into too much detail here.
But suffice to say you want something that’s pointed, but not pointy, and rounded, but not round.
(I know, these probably seem like subtle distinctions—but the handsome devil is in the details.)
How important is toe shape to making your shoes look sharp?
So important that it applies even when you’re not wearing shoes at all.
Neal often favoured dress boots like the pair below, which share a lot of the same characteristics as dress shoes, but go up to the ankle.
(A certain British superspy has been known to do the same.)
If you apply the same criteria to your boots that you do to your shoes and opt for a sharp and sleek toe shape, you’ll be able to wear them with everything from a three piece suit to a polo (more on those below).
The Neal Caffrey Hat
According to menswear lore (yes, there’s such a thing as menswear lore), mens’ hats like the fedora fell out of fashion on January 20, 1961.
That’s the day that John F. Kennedy was inaugurated president and refused to doff a hat, despite the frigid DC temperature.
But fashion is nothing if not cyclical.
If it’s true that real-life icon JFK killed the fedora back in the 60s, then it’s just as true that a pair of fictional style icons named Don Draper and Neal Caffrey breathed new life into it in the 20th century.
Draper’s fedora was a staple of the working man’s uniform back in his day.
But for 21st-century gentleman Neal Caffrey, it may have been the most ostentatious piece of menswear in his wardrobe.
And the way he rocked it with confidence and panache is a big part of the reason why fedoras have been reappearing on store shelves since White Collar debuted.
Neal opted for a short-brimmed black fedora, which was in keeping with his preference for skinny ties and slim lapels.
Like Sinatra before him, he most often wore it tilted on an angle, lending an otherwise old school look a bit of roguish, debonair charm.
The Tie Bar
Also called a tie pin or tie clip, the tie bar is another classic accessory that came back into prominence after the success of Mad Men.
It’s also one that Neal never left home without.
Because he was wearing skinny ties that look to be no longer than about two inches wide, Neal’s tie bars usually covered the entire width of his tie.
But another stylish option, often seen in the pages of GQ, is to go with a one-inch tie bar that only covers half the tie’s width.
When rocking a tie bar, remember that the best practice is to ensure all of your metal pieces are in the same family.
So if you’re wearing a silver colored watch, you’ll also want your belt buckle, tie bar and (depending on how far you want to take this) sunglasses to be silver as well.
But keep in mind that rules are made to (sometimes) be broken, and the tie bar is an opportunity to inject a little irreverence into your look.
Neal could often be seen rocking tie bars with a unique shape or color combo, which added a dash of fun to his look, and helped further distinguish him from the crowd.
The Pocket Square
Never one to ignore the little things, Neal Caffrey almost never let his chest go unadorned.
In yet another Mad Men-esque turn, Neal most often sported the same squared-off white pocket square that Don Draper and Roger Sterling wore decades earlier.
For my money, this is one of (and maybe the only) piece of Neal’s wardrobe that doesn’t hold up quite as well now that the show’s been off the air for awhile.
Don’t get me wrong: the square white pocket square is as classic as they come, and wholly unimpeachable.
But today you often see guys sporting more colorful options in shapes that aren’t so rigid, which feels like a natural evolution.
So the choice is yours:
If you want wear a pocket square that closely evokes Neal’s from the show, then stick with his classic white.
But if you want to dress a little more like Neal (probably) would if the show were revived today, then consider grabbing a colorful option that complements the colors in your tie.
Next Up:
Additional Elements
The Turtleneck
Neal didn’t wear a turtleneck very often, but when he did, he rocked it.
(Yet another thing he has in common with a certain super spy… who is obviously James Bond. Why am I playing this so coy?)
As you can see here, Neal kept it simple and classic with his turtleneck, opting for grey and pairing it with other pieces (his topcoat and hat) in similar shades.
Neal prefers a higher neck than 007, who opted for a mock neck in Spectre, but you should follow the lead of both style icons and go for one in a dark color that matches the rest of your get up.
The Leather Moto Jacket
As much as I love Neal’s suits, I have to admit: this might be my favorite piece he ever wore.
The moto jacket is as classic as it gets:
It looks masculine and cool in literally any era, and virtually never goes out of style.
What I especially like about Neal’s is that it’s simple and sophisticated.
A lot of leather jackets (especially the cheaper ones) have a ton of zippers and pockets, making them look loud and busy.
Neal keeps his simple, and looks all the sharper for it.
While his is no doubt from some vintage Parisian designer and just so happened to be pulled out of a closet the day he was released from prison, you can probably find a few well reviewed options on Amazon that look quite similar.
The Sunglasses
As with most things in his life, Neal Caffrey kept his sunglasses classic.
Neal opted for classic Ray Ban aviators, which coincidentally happen to be one of my picks for the most classic sunglass styles for men.
(If by “coincidentally” you mean “not at all a coincidence.”)
Neal preferred one of the all-time classic combos of gold frames with black lenses, but Ray Ban also offers aviators in a variety of colors and styles, so the choice is yours.
And as mentioned above, keep in mind your belt buckles, watch straps and tie bars when buying your sunglasses.
Best practice is to keep your metals in the same color family.
The Overcoat(s)
Neal most notably sported two different styles of overcoat.
One was a classic single-breasted top coat that paired perfectly with his slim fit suits, and the other was a double breasted peacoat that was long enough to cover his suit jacket.
Both are as rakish as you’d expect from Caffrey, so which one you opt for is really up to you.
While I’ve never shied away from admitting that I love a good peacoat, I have to admit that I personally have a soft spot for single-breasted top coats, especially over a suit.
The Watch
I guess White Collar couldn’t round up any watch companies as advertisers.
Because while they did multiple weird close-ups on Peter’s Ford Taurus, they did comparatively few on Neal’s watches.
Fortunately, the wristwear sleuths over at Watches in Movies were on the case, and provided a great break down of Neal’s preferred wrist piece.
Not surprisingly, Neal opts for a classic, a vintage Bulova Accutron, noted among watch aficionados as the first “electronic watch” because it was powered by a one-transistor electronic oscillator circuit.
While an actual vintage Accutron like Neal’s original can be hard to come by, Bulova is still very much in business.
They make a model called the Caravelle that looks a lot like Neal’s, and can serve as a great modern substitute.
The Polo Shirt
During his off-work hours Neal sported a number of different polo shirts.
And not surprisinbgly, they were usually in the same color family as his suit-shirt-tie combos:
Blues, greens, and burgundies.
While the colors and brands may have varied, the most important element always remained the same: the fit.
Neal’s polos always hugged his body perfectly along both his torso and his arms.
As I’ve written before, fit is the single most important factor when it comes to polos, and one that a lot of guys get wrong.
Below I’ve rounded up a few slim-fitting options that will evoke Neal’s swagger (assuming, of course, you order the right size).
You Know How to Steal Neal Caffrey’s Style
Now learn how to nail the dashing details
If you’ve read this whole thing, then you’re either having a very slow day at work, or you agree with what I said right off the top:
That Neal Caffrey is one of the sharpest characters to grace our screen in the past two decades.
(Or possibly both.)
Whether you wear a suit once a day, once a month, or once a year, you would do well to follow his lead and incorporate elements of Neal’s modern-classic wardrobe into your own.
Of course, buying the right clothes is only one part of the style equation.
If you really want to learn how to look great and outdress the other guys, you need to know how to nail the details.
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Great post! I always loved how Neal dressed on the show. Perfec representation of the classic gentleman imo
Thanks Adam! I totally agree. I love how Neal evoked a bygone era when guys could wear a fedora (without getting made fun of, that is).