A system (100, 200, 300, 600, 1000, 1100, 1200) for measuring a depth of a periodontal pocket, the system (100, 200, 300, 600, 1000, 1100, 1200) comprising: a frame comprising an eyeglass frame or head mounted frame or a combination thereof, the frame is configured to be worn by a user; at least one camera (104, 208, 324, 608, 1024, 1126, 1224, 1126), attached to the frame, configured to capture at least one 2D image of an intraoral target area, the at least one 2D image comprising a representation of at least a part of the tooth (322, 414, 508, 802, 902, 1016, 1018, 1402), a gingiva margin (316, 404, 502, 504, 806, 906) defined by a section of the gingiva adjacent to the at least a part of the tooth (322, 414, 508, 802, 902, 1016, 1018, 1402), a probe tip (312, 410, 516, 608, 704, 708, 716, 1030, 1304, 1408) when the probe tip is inserted into the periodontal pocket (412, 512, 1404); and a processor (106, 1202) configured to receive the captured at least one 2D image and determine, in relation to the gingiva margin (316, 404, 502, 504, 806, 906), an insertion length (406, 1416) of the probe tip (312, 410, 516, 608, 704, 708, 716, 1030, 1304, 1408) in the periodontal pocket (412, 512, 1404) by applying an image processing technique on information obtained about the probe tip (312, 410, 516, 608, 704, 708, 716, 1030, 1304, 1408) in the captured at least one 2D image, wherein the determined insertion length (406, 1416) represents the depth of the periodontal pocket (412, 512, 1404). a frame comprising an eyeglass frame or head mounted frame or a combination thereof, the frame is configured to be worn by a user; at least one camera (104, 208, 324, 608, 1024, 1126, 1224, 1126), attached to the frame, configured to capture at least one 2D image of an intraoral target area, the at least one 2D image comprising a representation of at least a part of the tooth (322, 414, 508, 802, 902, 1016, 1018, 1402), a gingiva margin (316, 404, 502, 504, 806, 906) defined by a section of the gingiva adjacent to the at least a part of the tooth (322, 414, 508, 802, 902, 1016, 1018, 1402), a probe tip (312, 410, 516, 608, 704, 708, 716, 1030, 1304, 1408) when the probe tip is inserted into the periodontal pocket (412, 512, 1404); and a part of the tooth (322, 414, 508, 802, 902, 1016, 1018, 1402), a gingiva margin (316, 404, 502, 504, 806, 906) defined by a section of the gingiva adjacent to the at least a part of the tooth (322, 414, 508, 802, 902, 1016, 1018, 1402), a probe tip (312, 410, 516, 608, 704, 708, 716, 1030, 1304, 1408) when the probe tip is inserted into the periodontal pocket (412, 512, 1404); and a processor (106, 1202) configured to receive the captured at least one 2D image and determine, in relation to the gingiva margin (316, 404, 502, 504, 806, 906), an insertion length (406, 1416) of the probe tip (312, 410, 516, 608, 704, 708, 716, 1030, 1304, 1408) in the periodontal pocket (412, 512, 1404) by applying an image processing technique on information obtained about the probe tip (312, 410, 516, 608, 704, 708, 716, 1030, 1304, 1408) in the captured at least one 2D image, wherein the determined insertion length (406, 1416) represents the depth of the periodontal pocket (412, 512, 1404).