Now that it is getting into the fall and winter, what items do you suggest?! I am just getting into cross-dressing, and I don’t know what to wear!
As you can tell from the picture below, I am absolutely the right person to ask about how to dress in colder months.
One of the many things I love about femme presentation is the amazing variety there are with clothes as the seasons change. For me, fall is all about layers, leather, skirts, and boots.
Pairing a short skirt with cardigan is a perfect way to show off our legs and stay (somewhat warm).
I love this look. I am not very confident about my skills pairing a skirt with a top but with the help of an H&M mannequin I think I… oh, who am I kidding? I saw a mannequin and just bought everything it was modeling.
I tend to stay away from sweaters as I tend to gravitate towards, ah, tighter clothes but I really like this outfit. I think I sexxed it up with the leather skirt.
I am also really into duster style cardigans. Not necessarily sexy but again, the leather helps… I completed this look with a bodysuit. I think having in a tucked in blouse is a good look with a skirt but I hate tucking in a top. A bodysuit is a wonderful cheat.
One thing that I hate about colder weather is needing to wear a jacket or coat. I think these add to my frame too much and emphasize my masculine shoulders. Buuut I think this look is cute.
Again, I balance (or contradict??) the look with a short skirt.
Honestly, I am not known for my practicality when it comes to my wardrobe. I am overdressed for everything, I am not shy about showing off my legs, my makeup is bold, my heels are high. If I have to dress for the weather I usually do it kicking and screaming. If I HAVE to take the cold into consideration I stubbornly (and admittingly unwisely) match a warm sweater or coat with a short skirt.
One common article in these pictures are boots. I rarely wear boots with a dress but there are exceptions…
I like the short skirt/boot pairing. Boots are a very autumn thing to wear.
I hope this helps?? I don’t think it does.
If anything, let me suggest two things:
- Wear whatever you want. Yes, you might be cold and you might look out of place but life is short.
- Look at what other women (or mannequins) are wearing. If it looks cute then wear something similar.
Love, Hannah
Have a question for me? Oh yes you do. Ask me here!
Hannah McKnight 
Bodysuits are wonderful items to have in your wardrobe. They help to keep your top “tucked” in so you can bend over without worry. I have about 10 now, mostly turtlenecks, both long-sleeved and sleeveless, that I wear in “boy” mode in the colder months. This is a must have item.
Another item to consider are sherpas, those fuzzy jackets. They are warm, they are fun! And you got to have fun. Get a good one and it will last for years.
Knee high boots are great for keeping your lower legs warm, and as Hannah pointed out, they make your legs look great.
Cali
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Great advice!!
Wish I could wear boots like that!
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Everything looks good to me in the pictures above. Like you said – life is short so have fun with it and dressing is a lot of fun!
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Enjoyed the pictorials and especially liked the pink skirt with lt blue jacket for the presentation. The hair and make up iso attractive and youthful looking.
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