A little known fact about the universe is that Vulcan attire did not contain any garment that was suitable for pulling over one's head. This was not usually something that Terrans noticed or even cared about, unless you were a Terran living on Vulcan or a Terran studying Vulcan cultural habits. This was simply a small factoid in itself.
It wasn't that Vulcan's were too haughty to possess couture that could be hoisted over the head in a swift motion. It wasn't that they simply hadn't caught up to the fashions. No, it simply was the fact that pull-overs such as Terran sweaters, t-shirts, and the like would get caught on the very distinguished points of the Vulcan ears.
Imagine Spock's dismay when all the clothing that he possessed from Starfleet was pull-over. His black undershirt, his uniform tunic was both pull over. The Starfleet issue sweaters and jackets were also pull-overs. Any commemorative t-shirt that he received from a conference he'd attended during his time at Starfleet was also a lobe-sticker. So, in order to forgo the embarrassing moment of getting stuck in his own clothing, Spock only removed said clothing in the privacy of his own quarters.
It wasn't until a fortuitous day, fortuitous because he'd finally gotten Nyota alone with him and away from Starfleet Academy to enjoy a quiet meal. She was always so focused, as was he, but tonight he wanted to focus on other things that had nothing to do with academia. It was a strangely cool night along the coastal city of San Francisco, cool enough so that he had to wear his Starfleet issued pull-over sweater. Nyota, however, had forgotten how cool the early spring nights tended to be and additionally forgotten her own sweater.
They sat, they talk, they ate, and enjoyed each other's company. At the end of their meal, she suggested taking a walk along the pier. Spock considered this a great idea, not only could they work off the meal they'd just had, they could spend more time getting to know one another on a personal basis, as Spock hoped.
Everything was perfect as they strolled along the pier, until Spock noted that Nyota was shivering. In a moment of pure chivalry Spock forgot the bane of his existence, pull-over sweaters. He stopped, tugged at the bottom of his shirt, crossing his arms and tugging upward. While in mid-tug, he quickly remembered that he was indeed on a collision course with his ears. Unfortunately, he was moving too quickly to stop, and although his brain shouted with a red alert siren, he was too late to stop his fate. Much like every pull-over item he'd been given, this, too got stuck on his ears, causing him to look like a person emerging out of a hole. He was, indeed, stuck inside of his sweater.
On a date.
With Nyota.
The silver lining to this dark cloud was that while he was trapped in the neck of his sweater, Nyota was currently preoccupied with the sweep of pale, hard tummy that was revealed to her eyes.
She was so embarrassed by her own vulgar leering and thoughts, that she didn't even notice his own embarrassment as she helped him out of the neck of his sweater. They were like the silliest version of the Gift of the Magi; the version O. Henry wrote as an outtake and stuffed it back in his wallet for something more serious.
After the whole ordeal was said and done, Spock was a little green and Nyota's face a little red. He'd dropped her off at the end of the night and she'd pressed a small and innocent kiss against his cheek. It wasn't until she was inside of her dorm that he noticed she was still wearing his sweater. It mattered not; he could still feel the heat of her kiss against his cheek and he allowed his ears to green a bit from the satisfaction. Spock measured the pros and cons and came away with one small truth: Buttons were overrated.
