Josh's ideas about fashion are somewhat incoherent, but follow some generally consistent themes. He frequently describes himself as a sexy goth bad boy, but on other occasions, has referred to himself as a hippie, a cowboy, and a dark wizard. He is often seen wearing his iconic black cowboy hat and spiked bracelets or chokers. His fashion could reasonably be summed up as “mall goth”, primarily consisting of the sort of things that Hot Topic and Spencer's sells.

Josh's fashion follows a distinct trend, easily separated into various costumes based on era, interests, and . This is made easier by the fact that Josh showers once a week, and wears the same clothes for weeks at a time.

In the formative years of the channel, Josh can be seen wearing a wide collection of various gothic and metal-themed T-shirts. Between this, his eyeliner and black nail polish, and the full head of hair, many regard this as Josh's “Lesbian Aunt” era.

Some well-known apparel from this time includes:

• The Zombie T-shirt of a rotting corpse wearing a tie
• The skeleton arm playing a bass

Josh's first major forays into questionable fashion territory by entering his Goth Biker phase. First, Josh would start covering his head with a black bandanna in order to hide his receding hairline, and debuting The Camouflage Vest. This style would gradually include other gothic accessories over time, but Josh's Tough Guy appearance was the most important thing during this saga.

There's something about cowboys. Maybe it's the style. Maybe it's what they stand for. Maybe it's because Wyoming never left the 1800s. Maybe it's just that Josh really likes Tombstone. Whatever it is, towards the end of the Ellen Saga, Josh would receive a new hat he would declare was Most Definitely What's Up. Gaining a second, wider one in later months known as the Pie High Hat, Josh would tear the sleeves off his Camouflage Vest and turn it into a true man's vest, as his hat continued to degrade. It is unconfirmed, but rumors persist that Josh sleeps in his hats, causing the additional damage.

Tied into the most famous of all outfits, Josh would debut an olive drab-esque jacket with The Rolling Stones' logo emblazoned on its back. Between the admission of baldness, the larger spectacles, and his overall wrecked appearance, Josh would best resemble a homeless Vietnam veteran. Clint always wanted a US Marine as a son, but this is the best he could manage.

With the appearance of NakedAndLaughing, Josh's style has deteriorated heavily over time. Fluctuating heavily, Josh can be seen in multiple various styles during this time, past and present, while also showing off a new wide-brim hat and his black jacket.

Josh's history with hats is long and varied, especially given his huge gourd-shaped head and proclivity to wear hats while he's asleep, as well as to hide his balding head.

Most infamous of all headgear, the Pie High Hat is a custom hat sent to Josh by a fan. Of all hats, it has remained the longest and has been the victim of the most abuse from Josh in recent years, most notably taking abuse during The broken cigarette incident when Josh smacked it numerous times against the arm of his chair. As of The Trailer Saga, the pie high hat has become so disheveled it closely resembles a tricorn hat. Only time will tell if it manages to stay alive, or if it will simply dissolve one day from Boglim sweat.

During The Ellen Saga. Josh would receive a low-quality plastic cowboy hat not unlike one would wear for a Halloween costume of imitation black leather, with a silver skull. This cowboy hat would barely fit Josh, and would quickly be destroyed through nonstop wear and tear.

Another infamous piece of fan mail, Josh would be gifted a fedora with a marijuanna pattern on it. As a pro-cannabis person, Josh would attempt to wear it, only to realize it was too small for his gargantuan, oddly-shaped head after attempting to force it on his head, causing him great distress and pain. After attempting to stretch it out using the vice on his wandmaking bench and nearly destroying the rickety table in the process, Josh would never show this hat off again.