At the Dawn of the 21st century, the field of specialty optical fibers experienced a scientific revolution with the introduction of the stack-and-draw technique, a multi-steps and advanced fiber fabrication method, which enabled the creation of well-controlled micro-structured designs. Since then, an extremely wide variety of finely tuned fiber structures have been demonstrated including novel materials and novel designs. As the complexity of the fiber design increased, highly-controlled fabrication processes became critical. To determine the ability of a novel fiber design to deliver light with properties tailored according to a specific application, several mode analysis techniques were reported, addressing the recurring needs for in-depth fiber characterization. The first part of this dissertation details a novel experiment that was demonstrated to achieve modal decomposition with extended capabilities, reaching beyond the limits set by the existing mode analysis techniques. As a result, individual transverse modes carrying between ~0.01% and ~30% of the total light were resolved with unmatched accuracy. Furthermore, this approach was employed to decompose the light guided in Large-Mode Area (LMA) fiber, Photonic Crystal Fiber (PCF) and Leakage Channel Fiber (LCF). The single-mode performances were evaluated and compared. As a result, the suitability of each specialty fiber design to be implemented for power-scaling applications of fiber laser systems was experimentally determined. The second part of this dissertation is dedicated to novel specialty fiber laser systems. First, challenges related to the monolithic integration of novel and complex specialty fiber designs in all-fiber systems were addressed. The poor design and size compatibility between specialty fibers and conventional fiber-based components limits their monolithic integration due to high coupling loss and unstable performances. Here, novel all-fiber Mode-Field Adapter (MFA) devices made of selected segments of Graded Index Multimode Fiber (GIMF) were implemented to mitigate the coupling losses between a LMA PCF and a conventional Single-Mode Fiber (SMF), presenting an initial 18-fold mode-field area mismatch. It was experimentally demonstrated that the overall transmission in the mode-matched fiber chain was increased by more than 11 dB (the MFA was a 250 ?m piece of 50 ?m core diameter GIMF). This approach was further employed to assemble monolithic fiber laser cavities combining an active LMA PCF and fiber Bragg gratings (FBG) in conventional SMF. It was demonstrated that intra-cavity mode-matching results in an efficient (60%) and narrow-linewidth (200 pm) laser emission at the FBG wavelength. In the last section of this dissertation, monolithic Multi-Core Fiber (MCF) laser cavities were reported for the first time. Compared to existing MCF lasers, renown for high-brightness beam delivery after selection of the in-phase supermode, the present new generation of 7-coupled-cores Yb-doped fiber laser uses the gain from several supermodes simultaneously. In order to uncover mode competition mechanisms during amplification and the complex dynamics of multi-supermode lasing, novel diagnostic approaches were demonstrated. After characterizing the laser behavior, the first observations of self-mode-locking in linear MCF laser cavities were discovered.