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Wearables have garnered significant attention in recent years not only as consumer electronics for entertainment, communications, and commerce but also for real-time continuous health monitoring. This has been spurred by advances in flexible sensors, transistors, energy storage, and harvesting devices to replace the traditional, bulky, and rigid electronic devices. However, engineering smart wearables that can seamlessly integrate with the human body is a daunting task. Some of the key material attributes that are challenging to meet are skin conformability, breathability, and biocompatibility while providing tunability of its mechanical, electrical, and chemical properties. Electrospinning has emerged as a versatile platform that can potentially address these challenges by fabricating nanofibers with tunable properties from a polymer base. In this article, we review advances in wearable electronic devices and systems that are developed using electrospinning. We cover various applications in multiple fields including healthcare, biomedicine, and energy. We review the ability to tune the electrical, physiochemical, and mechanical properties of the nanofibers underlying these applications and illustrate strategies that enable integration of these nanofibers with human skin.