Chicago-based street photographer trashhand is relentless; rising at sunrise, scouting at sunset, and climbing onto roofs and into abandoned buildings almost every day in search of the perfect image. Spend fifteen minutes with him, and it becomes very clear that while his photos may look candid, the strategy behind them is anything but. Always moving, he’s constantly looking for his next shot, watching for interesting architecture, steady cloud cover, or perfect symmetry.

It’s no wonder that trashhand has turned his photography into a successful career, working with brands like Nike and Puma to create original, edgy lookbooks for their products. More brands than ever are looking to urban photographers to give a new look to their campaigns, but it can be difficult to smoothly make the transition to professional photography. Luckily, trashhand was willing to show us exactly how to make professional shoots a success with a new class, Going Pro with Street Photography: Shooting Brand Lookbooks.

Before joining the class, check out 6 of our favorite shots for a reminder as to why trashhand’s photos caught the eye of brand execs in the first place: an expert eye, attention to detail, and a knack for getting seemingly impossible shots.

1. City Streets


While best known for his Chicago cityscapes, trashhand manages to capture the essence of any place he travels. The symmetry of the buildings and the two kids (doing handstands!) in this energetic photo provide a frame for the center subject, a boy who seems ready to jump into a handstand of his own. Plus, shooting at eye-level draws the viewer into the scene, letting us engage with the subject straight on, upping the shot’s intensity and intimacy.

2 & 3. The Spiral Staircase

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A classic trashhand shot is a look down a spiral staircase; the irresistible geometry can’t be beat. These two shots are essentially the same — both spiral staircases that seem to go on forever — but they tell completely different stories. In one, an old-fashioned staircase suggests traditional luxury. The other depicts clean, utilitarian metal. trashhand isn’t afraid to repeat motifs; just because you’ve seen one staircase doesn’t mean you’ve seen them all.

4. A Sideways Cityscape


Sometimes the best presentation of a photo can be a little…skewed. trashhand flipped this shot on its side before posting it to Instagram, drawing the eye toward the downward diagonal. “Don’t be afraid to explore, try new things, try new angles, line things up in weird ways.” trashhand says, “Just take the photo and see how it works out.” Consider your photo before you publish to see if there’s a more interesting presentation for your work.

5. Light at Night


trashhand believes “night photography really shows your skill in photography, your knowledge of lighting, and how you’re able to use and manipulate it.” That’s clear in this incredible photo of firemen in Chicago. trashhand uses the light from the firetruck and even the fire itself to give this photo an eerie glow. There’s a story beyond the edges of the photo: we can’t see the fire itself, but we know so much is happening outside of the frame.

6. Endless Symmetry


This stunning shot may be our favorite of the bunch. trashhand positioned his lens as close to the glass as possible to get a reflection that looks as real as the cityscape, creating a perfectly composed shot with balance and symmetry in spades.

Join trashhand’s new class, Going Pro with Street Photography: Shooting Brand Lookbooks, to learn how to pitch and work with brands, prep for a professional shoot, and edit photos with product in mind. Available with a Skillshare membership.

Written by:

Becca Cloyd