Abstract: Embodiments of the present disclosure are drawn to adjustable wearable headwear with integrated openings for accommodating one or more styles of hair. Aspects of the present disclosure also relate to adjustable headwear with integrated openings having a flexible member formed from one or more flexible elements (e.g., elastic bands, elastic straps, etc.) for permitting the headwear to adjust (e.g., expand or contract) based on a wearer's head size and/or hairstyle (e.g., a bun, a ponytail, or similar hairstyle), and for permitting natural contraction or expansion of the wearer's head. In an embodiment, the flexible elements may be arranged in a “ladder” pattern in a rear, flexible panel of the headwear. In another example of a headwear, the flexible elements may be arranged in a generally “X-shaped” pattern in a rear, flexible panel of the headwear. In such an example, two or more “X-shaped” elastic or flexible elements may be used.