I know it's spring now, so this probably isn't applicable anymore but I just started this blog a couple of days ago and this missed its chance. However, in my current situation my forced dressing still incorporates many winter items, even in the summer (fortunately for me, with the A/C on).
Several years ago my 2nd Mistress ordered me to write up a list of rules that would be the most humiliating for a sissy in winter. It was one of those lose-lose situations she would love to put me in... if she liked the rules they would become the new rules for outings. If she didn't think i did a good enough job I was likely facing a severe beating, several weeks of orgasm denial, and a super-unpleasant humiliating outing as well as being forced to re-do the list over and over until it satisfied her.
Here is the list I came up with. Luckily it pleased her. My "reward" was an outing to the mall where She picked out items that fit the criteria set in the rules and forced me to model them for Her in the store while making the decisions. Any time we bought something she made it clear to the salesgirl that it was for me.
1. Sissies should only wear outerwear and accessories in pastels or white during winter (pinks, purples, powder blue, etc.). Bold colors and neutrals are reserved for real girls.
2. All of your accessories should match perfectly with your ensemble. If you wear different color schemes, you should have a matching set of accessories for each.
3. All of your sissy winter clothes should have embellishments that make them more feminine: fur trim, fuzzy, pom poms, fringe, bows, buckles, etc.
4. Real girls get cold due to differences in body chemistry and physique, so good sissies should always bundle up to the fullest and have appropriate clothes for winter on their hands, feet, head/ears, and neck.
5. (from 4) If you are indoors in a public place, you must always keep at least two of your accessories on at all times (e.g. hat and scarf) to keep from "getting cold."
6. Sissies are only allowed to wear mittens unless you can only find gloves to match your ensemble.
7. Always wear boots if there is snow on the ground (they do not have to be winter-type boots).
8. If you are wearing a skirt or dress, always wear tights to keep your legs warm.
9. Hats are only permitted with a wig or natural long hair, if you have short hair you should only wear earmuffs or headbands to keep your true identity obvious.
10. Tops should all be tight fitting to show that sissy nipples get perky too in the cold.
11. Jingle bells are the perfect addition to show holiday spirit and draw attention.