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Crossdressing Outfitting Tips for Winter 2021

It’s late November already, and the coldest season is near. With that in mind, it’s the perfect time to start thinking about our winter outfits, and how to present ourselves in the most feminine way possible. However, due to the cold and all the snow, it may be difficult to do so. Warmer clothes tend to conceal our silhouettes, making it even harder for us to get convincing curves. Tight outfits, on the other hand, can end up making our brastforms look bloated. To avoid these we need to choose a proper outfit for the winter outfit as crossdressers, but many of us don’t know exactly how to do that.

 

Crossdressing Outfitting Tips for Winter 2021

 

My goal is to teach you how to achieve the desired balance between warmth and appearance. I’ll show you the best combinations for winter 2021, to ensure you look stunning this season. All of that while maintaining yourself warm and safe from the cold. Makeup is also important, so I’ll tell you how to take care of your skin during winter, and solve other common problems.

 

I’ll talk about all of that and even more throughout this article, to aid other crossdressers. Although everyone is unique, those general tips shall be helpful to the majority. With that in mind, I’ll teach you new techniques to help you crossdress during winter without any problem.

 

 

1. Accentuate your curves with the right clothes

 

What’s your very first reaction when you feel the temperatures dropping? Most people, especially men, will say they go grab their hoodies and sweaters. Women may do so on a number of occasions, but this is a huge mistake for crossdressers. I know, this kind of outfit is quite useful to keep us warm. But they tend to be made of a thicker, softer kind of fabric, which helps little to highlight any sign of our silhouette. As crossdressers, we want to look as feminine as possible, and a good percentage of the feminization of our figure comes from our curves. Achieving an hourglass figure is the key for a man to pass as a woman, so we need to figure out better alternatives. But what kind of outfit can keep us warm and feminine at the same time?

 

Crossdressing Outfitting Tips for Winter 2021

 

My answer to that is blazers, light jackets and coats, even better if they have buttons. The feminine ones, at least, often come with a sewed area on the sides, making them narrower around your waist. This narrow spot ensures that your coat will keep its shape, enhancing your silhouette. They go well on top of dresses, and allow you to try out many combinations that you couldn’t try if you were to use a sweater or a hoodie. I’ve mentioned buttons as well, since they boost the aforementioned effects. Their purpose is to hold together both sides of your jacket, blazer, coat, etc, preventing it from getting too loose. They also help the narrow part around your waist to blend in with your silhouette, enhancing the hourglass effect. If you feel too restricted by the buttons, you can keep some of them open. I usually leave most of them like that, closing only a couple near my belly. This way, I keep most of the positive effects, but grant a larger degree of movement freedom.

 

2. Smoothen your figure with stockings and sleeves

 

The same problem we have with our curves and waistlines, may also happen to our legs and arms. You see, females tend to have smoother limbs, and achieving that sure helps us to achieve a more feminine overall appearance. In terms of crossdressing, what really matters is to have fun and dress up in clothes that you enjoy. However, the goal of some of us is to pass in a convincing way and to be treated as women naturally. If that’s your case, every detail is important and can make a real difference. To feminize your legs in the winter, however, you may need to adapt, since the classical sheer pantyhose won’t protect you from the cold.

 

Crossdressing Outfitting Tips for Winter 2021

 

A technique called “layering” may be useful. It consists of wearing multiple layers of hosiery, as the name suggests, but there’s a little more to it than that. You see, wearing a couple of opaque black tights from a high denier will be enough to keep you warm. But it won’t highlight your legs as much as possible, so you’ll be missing the full potential of this technique. My tip is to combine different colors of hosiery to create a more natural effect. A big part of convincing crossdressing can be described as illusionism, and this aspect is not so different. Instead of two high-denier tights, I suggest you use three medium-denier ones. Two beige ones and a black one should be spot on for this. The first two will do the job of smoothening your legs, and the last one will ensure it looks more natural. The combination of the three pieces of stocking should be enough to keep your legs warm, but you can use some feminine socks as well to improve it.

 

Crossdressing Outfitting Tips for Winter 2021

 

If your plans involve jeans or outfits that don’t go well with hosiery by itself, you can merge them. Use a thick opaque black pantyhose under a pair of feminine tight jeans, for example. This way, you grant some extra warmth, while keeping your legs well-outlined. Darker tones of jeans (or leggings, if you prefer) are recommended, to boost the outlining potential of this kind of outfit. A similar principle can be applied to your arms as well. Use long sleeved coats made of elastic fabric, in a way that it outlines the entirety of your arms. Jeans jackets may also do the trick, but they tend to be a bit more loose on the openings. To feminize your clothes, lace gloves are most commonly used, but they may not protect you. A warmer option may be knitted gloves, since they hide your masculine hands and keep them warm. But if you really want to show off your newly polished nails, fingerless gloves should provide enough protection. Silicone crossdressing gloves are also an option for that, even more if you combine them with lace gloves, as they serve as a counterbalance.

 

3. Make use of practical accessories

 

Once you decide between these methods of keeping yourself warm, consider a few more accessories. They may complement your look and make you more comfortable. Scarves are useful not only to protect you from the cold, but also to hide your Adam’s apple. If you’re familiar with silicone breast form vests, you can see how a scarf can be helpful. It conceals the transition between the silicone and your real skin.

 

Crossdressing Outfitting Tips for Winter 2021

 

I also want to talk about bonnets and beanies. It’s not a secret that they do a wonderful job in protecting your head from the cold, but they can also make your wigs look more convincing. That’s because cheap wigs that don’t have a lace are very limited in terms of realism. Most of them use bangs to hide the transition from your actual scalp to the fake one, and some may not stay in place. You can fix that with a well placed beanie, hiding the top of the wig and making it more convincing. I love both of these solutions, since they are a nice touch to winter outfits and quite fashionable for the holidays.

 

Crossdressing Outfitting Tips for Winter 2021

 

As we are talking about winter 2021, it may be helpful to tell you what’s going to be trendy this year. In terms of accessories, knitted beanies are a hot take, especially on bright colors. Bucket hats are also a good option, but they are better this year in darker tones, such as dark blue. Due to the pandemic we had to face during these last two years, face masks may be required. But you can style them as well. Summer had people wearing white or light colored ones, so black is a good choice for winter.

 

4. Try to distinguish yourself from the landscape

 

Another common winter problem is that blending in with the landscape is easy. Crossdressing is way more enjoyable if you’re able to distinguish yourself and leave a mark. If you’re used to going out while crossdressing, you know what I mean. When we’re trying to keep ourselves warm and comfortable, it’s common to choose black or dark gray coats, as darker colors tend to retain more heat. But doing that only makes it even more difficult to be noticed, since it draws little to no attention. Brown leather coats are not gonna help you either. I mean, they sure are fashionable. But, unfortunately, tend to blend in with the bare leaf trees and do nothing to highlight our feminine features.

 

Crossdressing Outfitting Tips for Winter 2021

 

Then how do we distinguish ourselves during the winter season? My advice is to incorporate brighter colors into your outfit. But not too bright, since pure white and off-white colors will blend in with the snow, making you almost invisible. I’m talking about flashy colors, such as red, pink, yellow and such. Green is another good example, since the trees will be lacking leaves. Coats come in a wide variety of colors nowadays, and bright colors are trendy. All you have to do is make sure you remember the first technique when choosing them. This way, you can keep yourself visible and look feminine.

 

Crossdressing Outfitting Tips for Winter 2021

 

Of course, bright coats are not the only way to keep yourself visible during winter. You can be noticed as well if you choose the right color for your accessories. For example, you can keep black as the base tone for your outfit, in order to better outline your silhouette. But to ensure you’re distinguishable from the landscape, use bright colors in strategic areas. A colorful scarf will show you’re there, and ensure no one notices your adam’s apple. A flashy skirt with matching suspenders, on the other hand, will enhance your hourglass figure. Belts, necklaces and earmuffs are other good choices to make your outfit more colorful and visible.

 

5. Makeup tricks and suggestions

 

Your makeup is the core of the illusion, as it’s what transforms your facial features from male to female. Even though it’s true, I guarantee you won’t want to stick to the basic stuff if you plan on leaving a mark. Winter is a season that brings a drastic drop in humidity, with little moisture in the air and colder temperatures. We normally start by doing our usual makeup, following the same principles crossdressers are familiar with. That is, contouring our jawline, cheeks and nose, applying eyeliner, highlighter and mascara. In most cases, that’s more than enough to make us feel feminine and beautiful. But with the complications that winter brings, things get more complicated. It’s easy to harm our skin, which is dry and sometimes flaky due to dehydration. The effects of cold and dehydration are visible through makeup and will have an impact on the way you look. With that in mind, the tips I bring you here are aimed to help you avoid this kind of situation.

 

● Moisturize more often

 

Crossdressing Outfitting Tips for Winter 2021

 

Of course, this is the best way of preventing dehydration, and a very useful skincare tip. A well moisturized skin is softer, giving your face a smoother complexion and a natural glow. Use an extra massaging time to make sure it penetrates your skin, so it has the greatest effect. Another good way to ensure your skin stays moist, is to use moisturizing foundation. As it will be in constant contact with your skin, the foundation prevents it from drying too quickly after you leave your house.

 

● Avoid powders

 

Crossdressing Outfitting Tips for Winter 2021

 

Your goal is to achieve a soft skin, making your face look more feminine. Powders in general may have the opposite effect during winter, as they may make your skin look dull and rough. That’s due to the way they react to the cold, and to the fact that they accelerate dehydration of your skin. Instead, use a good complete correction cream in a similar tone to your skin. Most cc creams have sunscreen and moisturized included, making them ideal to protect your skin from the harsh winter weather.

 

● Play with colors

 

Crossdressing Outfitting Tips for Winter 2021

 

To add some contrast to the white of the snow, don’t forget to add some color to your makeup. Most colors will work for eyeshadow, and a dark maskara may fit most scenarios. However, it’s nice to buy some replacement to your supply for winter. That’s to ensure the cold won’t wear down your products, making them crack. Blush is also recommended during winter, as it adds a healthy aspect to your skin. Don’t be afraid to experiment with different shades of blush, from dark red wine to a more delicate pink. The point of experimenting and playing with colors is to find out what works best for you.

 

6. Use less stuffing and smaller breast forms

 

Crossdressing Outfitting Tips for Winter 2021

 

We’ve seen that tighter clothes are useful to help you keep your silhouette distinguishable. However, you’ll have to learn how to avoid a bloated look in your chest due to your fake breasts being compressed. Reducing their size is the easiest way to do so. If you use stuffed underwired bras, try using normal ones instead. Another tip is to use pushups and about a third of the stuffing. For those who use breast forms, make sure they have gel filling, as cotton may lose its shape when compressed. Go for a cup one size smaller than what you normally use, and get nipple pasties to prevent the fake nipples from showing through your clothes. My last advice on this subject is about the material of your clothes. Elastic fabric is my recommendation, since it allows your fake breast to have a certain degree of movement. The extra realism is worth it, but make sure to check if the fabric is thick enough to protect you from the cold.

 

7. Choose a stable, yet feminine footwear

 

Crossdressing Outfitting Tips for Winter 2021

 

Many crossdressers choose heels to feminize their feet, and to help them walk in a more feminine way. However, it’s difficult to walk on snow, lush and ice using heels. Such surfaces are slippery, so walking over them in this kind of footwear can be a dangerous task. Our tendency is to wear chunky boots with larger surface areas, so we are less likely to fall. Not only are they not attractive or feminine, but it’s also difficult to walk like a lady in them. To solve this problem, look for feminine boots, preferably with wedge heels. They are cute, feminine, and allow you to do your female walk the same way you would do in heels. In addition to that, they have enough surface area and attrition to prevent you from slipping in the snow.

 

Crossdressing Outfitting Tips for Winter 2021

 

But your boots should also be in touch with the current trends. For winter 2021, try minimalist footwear in darker tones. Avoid boots with too many details or too many colors. Leather brown and buff are common colors for this time of the year, but my recommendation are bluish gray or black.

 

Crossdressing Outfitting Tips for Winter 2021

 

A good makeup is as important as the rest of your outfit. You shouldn’t neglect any aspect of crossdressing, since the whole is composed of many smaller parts. Each one plays a major role in creating a convincing female presentation of yourself. But please remember that these are nothing but tips and guidelines. You should dress up as you like, or in a way you feel comfortable with. Each crossdresser is unique and has its own needs, and I hope this article helps some of you to fulfill yours.

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