In Asian cultures it tends to be looked down in for having dark skin. Umbrellas, skin lightening creams and being covered up are as prevalent today as they have been for decades and centuries. It seems that staying out of the sun with parasols and gloves was fashionable in western culture right up until the end of the Second World War. Was there ever a time previous to that where having tanned skin was seen as a positive?
Having a nice tan has been considered, in modern Western cultures at least, as a sign of good health and even higher status. Tanning has been considered an easily discernible visible marker that better highlights the contours of the skin, making those contours stand out more, and is seen by many to denote a fresh, healthy glow. Western studies have actually been done that show people today perceive an individual who is well tanned as being healthier and more attractive. Particularly in earlier decades past, being tanned in the western world denoted an ideal that the individual was both well traveled and was able to have a carefree, even wealthy lifestyle. Carrying a decent tanned skin tone was seen as a type of status symbol, particularly during the cold weather months, because it was thought that only the well-to-do and wealthy could afford the time and travel and carefree lifestyle to get a natural deep tan.
In fact, it has been scientifically shown in the western world cultures that people are perceived as being more attractive with a "healthy glow" natural-looking tan than without.
Prior to the industrial revolution, being tanned used to not really be a desirable thing, because it was deemed better to be pallor or light-skinned, as that denoted a more "noble" life of being able to afford to just "live indoors", whereas tanned people were seen as a visible demonstration of a person whose life was based on working outdoors in the fields under the sun all day, which tended to lower one's social status.
In the 1920s, Coco Chanel, the famous French fashion designer, actually played a hand in the idea of tanning becoming a popular thing to do and to show beauty, wealth, and health, with some even crediting her as being the initial queen of the start of the "sunbathing craze". After several photos of her being very well-tanned during a cruise she took on the Mediterranean Sea in the 1920s circulated in the west, the concept of sunbathing or tanning to improve appearance and try to demonstrate high status really took off among the wealth and not-so-wealthy alike. Prince Jean-Louis de Faucigny-Lucigne, a friend of Coco's, when asked about this very topic, even later proclaimed that "I think she [Coco] may have invented sunbathing. At that time, she invented everything."
Prior to that however, it seems that maintaining a pale skin tone was considered to be of more desirable appearance, as it denoted one could carry out a life of indoor leisure as opposed to having to toil outside under the sun.