How to Dress Like Sergeant Will Simpson (Jessica Jones) | TV Style Guide

How to Dress Like Sergeant Will Simpson

Netflix Jessica Jones Sergeant William Simpson

Will Simpson is the puzzling policeman who does a lot more than protect and serve for Trish Walker and her adopted sister, Jessica Jones.

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Sergeant Simpson plays dual roles throughout the series - at times portraying both a hero (as Trish Walker’s unlikely bad-boy lover) and even a villain (by going against Jessica Jones’ wishes, relating to the proper way to address the Kilgrave situation).

If you know your Marvel history though, his identity shouldn’t be much of a mystery.

Ahead you will find a guide to help you match the style of Sergeant Will Simpson.

Clothing Purchasing Guide

We Recommend:

Jackets & Shirts

Jeans & Boots

Weapons & Accessories

Will's style overview:

  • Black or brown leather jacket
  • Dark jeans
  • Work boots
  • Aviator sunglasses

The Hat & Jackets of Sergeant Simpson

Will Simpson Brown Leather Jacket

Sergeant Simpson is known to wear at least one other hat (not including his standard issue NYPD uniform cap).

The hat he is noted to wear is a plain navy blue baseball cap. He is seen wearing it while carrying out on an operation to stop Kilgrave.

This plain baseball cap in navy blue color is a perfect match to that worn by Will Simpson on Netflix Jessica Jones.

Sergeant Simpson's Jackets

Whether it is your goal to assemble a complete, screen-accurate Will Simpson costume, or you would just like to inject some of that stylish Sergeant Simpson flavor into your own wardrobe, you’re going to need one of his fashionable jackets.

Will Simpson has noted to wear at least two separate jackets throughout the first season of Netflix Jessica Jones.  One black, and one brown biker style jacket. Both appear to be leather with slight variations in style.

This leather jacket in brown is nearly indistinguishable from the one worn by Will Simpson on J.J.

Here is a moto style leather jacket in black that is a different style from the one previously mentioned, and it’s also a great match to Sergeant Simpson’s jacket.

Will Simpson's Luxurious Legwear & Shirts

Considering he was/is involved with some secretive, military super-soldier program, it isn’t much of a surprise that Will Simpson’s style can range from completely casual and basic to strictly tactical.

Which is exemplified best when you look at the different types of shirts he wears.

He is noted to wear a charcoal gray long sleeve sweatshirt and a military green t-shirt, both of which he wears under one of his sharp leather jackets.

Here’s a charcoal sweatshirt that is nearly identical to the one worn by Simpson.

This t-shirt in military green is another great match to his style.

Will Simpson's Legwear

Netflix Jessica Jones Will Simpson

Will Simpson’s legwear is arguably the most simple element of his already pretty basic wardrobe.

Once again, not including his NYPD uniform, Will has been known to wear a few different sets of men’s jeans. Usually in a darker shade of blue.

These Levi's 569 jeans in Kale color are an excellent match to the ones worn by Will on Jessica Jones.

Sergeant Simpson's Underwear & Footwear

As i mentioned earlier, Will does become involved romantically with Jessica’s adopted sibling Trish.  As you might imagine, this leads to seeing Will and Trish during some of their most personal moments.

So if you are in need of some under armor with the freedom to move freely and just enough support, I would suggest Will Simpson’s underwear of choice: black boxer briefs.

Here are some boxer briefs in black that are nearly identical to those worn by Sergeant Simpson.


Will Simpson is known to go around stomping the asses of just about anyone who gets in his way when he’s ON his meds. Which, as you may have deduced, consists of red, white and blue performance enhancing substances.

Other than his last name, this is the biggest clue that Sergeant Simpson may in fact turn out to be the infamous Marvel villain ”Nuke!”

At any rate, he is known to wear tan colored, lace up work boots.

These tan boots by Ever Boots match those of Will Simpson to a tee.

Simpson's Weapons & Accessories

Will Simpson Police Officer Uniform

While going around kicking butt, taking names and demanding “The red ones,” Sergeant Simpson is noted to carry a few different weapons and accessories.  Some of which no Sergeant Simpson cosplay should be without.

These brown lens aviator sunglasses by Owl are a great match to those worn by Will on Netflix original series Jessica Jones.

Here is an American flag Zippo lighter that is not only a great match to the one carried by Will, but it’s just damn awesome!

This airsoft gun is modeled after a Smith and Wesson pistol and it’s a great match to the pistol carried by Sergeant Simpson.

Finally we have this Umarex airsoft pistol that has been modeled to resemble a Glock 19, just like the one used by Sergeant Simpson.

In conclusion I have come to appreciate the simplicity of Will Simpson’s civilian garb, and I look forward to see how the characterization is handled in his inevitable future appearances.

As always, hopefully we have assisted in your hunt for appropriate matches for the clothing worn on your favorite shows. Please inform us of anything you feel may have been overlooked.

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