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.