The Well Dressed PI — Guest Post By Thomas H. Humphreys, Private Investigator

Meet Thomas H. Humphreys, the best-dressed PI since Nick Charles. Humphreys, like Charles, knows what that hole in the lapel is for—and what ingredients make the best Montgomery Fizz. Humphreys is one of the primaries at [FIND] Investigations out of Nashville. After you’re finished here, head over to his blog for more adventures.

The Well Dressed PI

I think we’ve lost our way. Casual Fridays, corporate logos, and “authentic” hipsterism have shoved proper style to the back of the closet.

There was a time when men dressed like men. Search for 1920s men’s style and you’ll see. Watch an episode of MadMen and you’ll see. Hell, even stream an episode of Rockford on NetFlix, you’ll see. Men used to dress like men. They had style.

Sam Spade The old-school gumshoes, the creations of Dashiell Hammett and his contemporaries, dressed like gentlemen—though, it seems that everyone in that era dressed to impress. Let’s be clear, the clothes do not make a man a gentleman. We’ll just accept as a given that being a gentleman is the foundation upon which we’ll build our wardrobe.

I spend a lot of time with federal agents, detectives, and other private investigators. The feds understand: they apparently have a dress code. Police detectives sometimes get it (see this story about best dressed detectives). PIs are, quite possibly, the worst.

Still, in my cadre of private dicks, there’s a sense of professionalism that seems to demand a higher standard.

In the office and at leisure — The PI as Professional — Dolling up for clients

FIND InvestigationsOffice — Appearance is key, first impressions paramount. I never go to a client meeting, deposition, or court without dressing for the occasion. My clients expect a certain style from me. I wear denim often and am completely comfortable going to meet a long term client sporting a pair of jeans, mid-tan shoes and belt, pressed oxford cloth shirt, and an odd jacket, maybe even a bow tie.

That’s as casual as I get. For depositions, a pair of gabardine slacks, likely grey, nice sport coat, and definitely a tie. Court demands a suit, sometimes three-piece, but always a suit.

FIND InvestigationsThese are fairly easy ideas to grasp. It’s the minutia that makes a difference. Ties, pocket squares, cuff-links, these small items add color and elegance to any outfit. Ties should be classic and colorful. Ties should never have products or cartoons patterned across them, never. Pocket squares should not match the tie, rather complement it. Again, color and quality are of utmost importance. Cuff-links should be metal, simple, and match your belt buckle and watch.

Leisure — Those of you who read the [FIND] Investigations blog on a regular basis know my fondness for a hand-crafted cocktail and fine wine. I love cocktail hour. Here in Nashville, we usually head to The Patterson House or the Oak Bar for cocktail hour. It amazes me how people show up to a classy bar in shorts and t-shirt.

When we host our Bow Ties and Bourbon events once a month at The Patterson House, everyone is encouraged to dress. The wonderful thing is this: a table full of judges, lawyers, investigators all in their finery somehow makes the whole joint feel classier, like a throwback to yesteryear, gentlemen and ladies behaving as such.

Again, these are the faces we show in our capacity as professionals. The real fun starts when the work begins.

In the field — The PI on surveillance — blending in

Assignment — Surveillance
Location — New Orleans
Weather — Sweltering hot with turgid skies
Time — 9:00 PM — until
Conveyance — Foot mobile

This is where creativity and a sense of style allow the professional investigator to blend in perfectly. I use this example because we just happen to have a picture to go with it.

FIND InvestigationsLast month we traveled to NOLA for a bit of sub-rosa work. Our team costumed to match the surroundings. White linen pants and a seersucker jacket, with a rich red pocket square, allowed us to melt into the background at Galatoires, all the while observing our subject and documenting his activities. We strolled, in a classic front-and-follow maneuver, across Canal Street to the Sazerac Bar in the Roosevelt Hotel over on Baronne, never once drawing unwanted attention. We sidled up to the bar and continued our surveillance (unfortunate mocktails in hand), the subject completely unawares.

It’s not always like this. Sometimes you have to get down and dirty (trash collectors uniform, hard hat, safety-vest), but it’s the urban neighborhood surveillance that allows us to have a bit of fun, look like we care, and blend in at the same time.

This little exercise in styling a PI for a specific job is our introduction to a quarterly column under the Sartorial Sleuth heading. We’re going to call this tri-monthly exercise The Sartorial Sleuth, dressed for success(ful surveillance).

Also see this posteditor.


  1. Apparently PI’s have more time to respond to requests for service than does the public sector, because Joe and I seldom had a chance to change our shirts and ties, let alone our entire ensembles. Sometimes all week.

    And pocket squares?. If we’d have shown up wearing cute decorations in our upper pockets instead of badge holders we would have been laughed off the scene by “uniforms”.
    Did have one stakeout where that pinkish seersucker outfit would have come in handy, but that’s another story.

    OK, I’m a little jealous. Get over it.

  2. You can never take too much care over the choice of your shoes. Too many PI think that their shoes are unimportant, but the real proof of an elegant investigator is what is on their feet.

Leave a Reply

Your email address will not be published. Required fields are marked *