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I get bored in the Ashlands, but could roam Sheogorad and the eastern coastline for hours. Clothing & Equip? Why, you gear up for the encounters. There be Daedra about!

A Thalmor agent at a social event spotted the Legion Captain in uniform, with his service blade at his hip. Incensed that he would attend so armed, she crossed the room to grill him.
"Expecting trouble this evening, Captain?" she sneered.
"No, ma'am," he replied without hesitation, employing a professional's smirk as he spoke. "Had trouble been expected, I would have brought my ebony."

Where do I like wandering on Vvardenfell? Pretty much everywhere. Well, okay, I don't typically wander around inside the Ghostfence for fun[1], but everywhere else is fair game.

If I had to pick favourites I'd have to go with the Ascadian Isles, with its lush greenery and wildflower gardens, and Azura's Coast, with its fantastic mushrooms. But pretty much everywhere on the island has its own type of charm for me, from the rocky highlands and beaches of Sheogorad to the humid swamps of the Bitter Coast, the smoking lava pools of Molag Amur, and the barren wastes of the Ashlands which have a stark beauty all their own.

Now, where my characters like to wander around, that's a different story. My characters will prefer different regions based on their backgrounds. For example, one of my characters (Kidwen) is a Dunmer-Bosmer hybrid (Dunmer father, Bosmer mother); her (brief) backstory is that her father was originally from the Urshilaku Ashlander tribe before he left it to wander around Tamriel. He was killed when Kidwen was only a few months old, so her only knowledge of him came from the stories her mother told about him[2]. So naturally, when Kidwen went to Vvardenfell to discover her father's heritage for herself, she loved roaming around the Ashlands where her father had grown up (even in ash storms). Contrast this with my character Tynian Adonius, an Imperial Legion trooper and Imperial Cult adherent, who grew up in Cyrodiil. He'll stoically endure the hardships of marching through Molag Amur or the Ashlands when duty requires it, but much prefers to stick to the civilized areas of the island.

Clothing and equipment? Whatever suits the character and the mission.

Note 1:Note 2: