Calisthenics is a form of training broken down into various functional movements, usually bodyweight push and pull movements. Calisthenics also incorporates leg exercises, but in my opinion, leg movements are optimal when adding weight or explosive movements that classify as plyometric exercises.
With the push and pull calisthenics movements bodyweight only can build a great base, but at a certain point in your calisthenics journey, you will need to increase resistance or make the movement more difficult with an advanced variation.
It could take days to go through all of the push and pull progressions, but we only need a short conversation about the best ways to increase strength with weighted calisthenics. Two movements. Weighted Pull-ups and weighted dips.
Of course, you can add weight to almost any calisthenics movement with the addition of a weight vest, but the two weighted movements that will best carry over into improving strength for more advanced movements are going to be pull-ups and dips.
Pull-Ups
Pull-ups are the ultimate compound pull movement, engaging the core, arms, and practically every muscle in your back (Example below). Weighted Pull-ups build strength for advanced movements, such as muscle-ups, front levers, and row variations.
Pull-ups also offer several aesthetic bonuses in addition to the performance gains.
V-taper look
Bigger shoulders
Accentuates definition in the upper back
Christmas Tree Definition in the lower back
Bigger Biceps and Forearms

So how do you know when to start adding weight to pull-ups?
10 controlled, full range of motion pull-ups unbroken
15 reps and sets style pull-ups unbroken
Hitting a plateau in pull strength from bodyweight pull-ups
Desire to add size to your back and shoulders
Dips
Dips (Specifically Parallel Bar Dips) are another holy grail movement in the world of calisthenics. A compound that engages the core shoulders, chest, and triceps. Dips give you transferable strength into more advanced push movements such as tuck planche push-ups, handstand push-ups, and bent arm planche.
Aesthetic Gains from Weighted Dips
Bigger, more defined chest
Bigger Triceps
3D front Delts
More visible abs

When is it time to add weight to your dips?
12 controlled, full range of motion dips
Arms hitting a 90 Degree angle (Example in image above)
Strength Plateau reached with unweighted dips
Desire to add size to your arms, chest, and shoulders
When beginning your weighted calisthenics journey, start off slow. Add lighter weight that you can rep 5-8 times (Pull-Ups) 8-10 reps (Dips), then add weight incrementally. Maxing out reps or weight daily is the wrong way to build up strength. It's an easy way to break down your body.
As I stated before, you can add weight to almost any calisthenic movement, such as push-ups, handstands, muscle-ups, and even static movements like front and back levers. As you continue to build on your solid foundation, the more you can experiment with new movements and push the limits with more resistance.
As I like to say, we are our own science experiments. Continue the journey of learning how to optimize your body
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