How to Wear Women’s Clothes as a Man: A Comprehensive Guide (2023)

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Important considerations when wearing women’s clothes as a man

When it comes to wearing women’s clothes as a man, there are several important considerations to keep in mind. First and foremost, it’s essential to be comfortable and confident in your choices. Society may have certain expectations or judgments, but ultimately, it’s about expressing yourself authentically.

Another consideration is finding the right fit for your body shape. Women’s clothing typically has different measurements and proportions compared to men’s clothing, so it’s important to take accurate measurements and consult size charts when shopping. Additionally, consider the occasion or setting where you plan to wear women’s clothes – some styles may be more appropriate for casual settings while others are better suited for formal events.


  • Comfort and confidence
  • Finding the right fit
  • Determining appropriateness for different occasions

Determining the correct size for men shopping for women’s clothing

Determining the correct size when shopping for women’s clothing as a man can be a bit challenging due to differences in sizing systems between men’s and women’s apparel. However, with some careful measuring and attention to size charts, you can find the right fit.

The first step is taking accurate measurements of your body. Measure your chest/bust, waist, hips, and inseam. Compare these measurements to the size chart provided by the brand or retailer you’re purchasing from. It may also be helpful to check reviews or reach out to customer service if you’re unsure about sizing.

Sizing tips:

  • Take accurate body measurements
  • Consult size charts provided by brands/retailers
  • Check reviews or reach out to customer service for guidance

Styles and cuts of women’s clothing suitable for men to wear

Exploring Different Styles and Cuts

When it comes to finding women’s clothing that is suitable for men, there are a variety of styles and cuts to consider. One popular option is the boyfriend fit, which offers a more relaxed and oversized look. This style can be found in jeans, blazers, and button-down shirts. Another option is the A-line silhouette, which flares out from the waist and can be flattering for all body types. This style is commonly seen in dresses and skirts.

Additionally, exploring different necklines can also help create a more masculine appearance. V-neck tops or dresses can elongate the neck and provide a more angular shape. Crew necks or boat necks can also be flattering options for men looking to incorporate women’s clothing into their wardrobe.

Tips for Trying on Women’s Clothing

  • Take accurate measurements before shopping to ensure proper fit.
  • Start with basic pieces like t-shirts or jeans before experimenting with more daring styles.
  • Don’t be afraid to try on different sizes as women’s sizing can vary between brands.
  • Consider alterations if needed to achieve the desired fit.

Clothing Brands Catering to Men Wearing Women’s Styles

  • Billy Reid: Known for their high-quality fabrics and tailored fits, Billy Reid offers a range of women’s clothing options suitable for men.
  • Zara: Zara has a wide selection of trendy women’s clothing that often features gender-neutral designs.
  • Diane von Furstenberg: This brand specializes in stylish dresses that can be easily incorporated into a man’s wardrobe.

Tips for selecting comfortable and flattering fabrics in women’s clothing

Choosing Comfortable Fabrics

When selecting women’s clothing as a man, it is essential to prioritize comfort. Opt for fabrics that are soft, breathable, and stretchy. Natural fibers like cotton or linen can provide breathability and prevent overheating. Additionally, consider fabrics with a bit of stretch, such as spandex blends, to allow for ease of movement.

Fabric Options for Flattering Fit

  • Ponte Knit: This fabric offers structure and stretch, making it ideal for fitted dresses or pants.
  • Jersey: Jersey fabric drapes well and is often used in tops or dresses to create a flattering silhouette.
  • Silk: Silk has a luxurious feel and can add elegance to any outfit. Look for silk blouses or dresses that can be paired with other masculine pieces.

Taking Care of Women’s Clothing Fabrics

  • Follow the care instructions on the garment’s label to ensure longevity.
  • Avoid using harsh detergents or bleach that could damage delicate fabrics.
  • Consider investing in a steamer to remove wrinkles without causing damage.

Incorporating women’s tops into everyday outfits as a man without looking out of place

Choosing the Right Women’s Tops

When incorporating women’s tops into your everyday outfits as a man, it is important to choose styles that are more gender-neutral or can easily be styled in a masculine way. Opt for basic t-shirts, button-down shirts, or sweaters that have simpler designs and avoid overly feminine details like ruffles or lace. Stick to solid colors or subtle patterns that can easily blend with your existing wardrobe.

Pairing Women’s Tops with Masculine Pieces

To avoid looking out of place, it is crucial to balance the femininity of women’s tops with masculine pieces. Pair a flowy blouse with tailored trousers and dress shoes for a sophisticated look. For a more casual outfit, wear a fitted t-shirt with jeans and sneakers. Layering is also an effective technique – try wearing a women’s cardigan over a plain t-shirt and pair it with chinos and loafers.

Confidence is Key

The most important aspect of incorporating women’s tops into your everyday outfits as a man is confidence. Own your style choices and wear them proudly. Remember that fashion has no gender boundaries, and by embracing different styles, you are expressing your individuality. Don’t worry about what others may think; focus on feeling comfortable and confident in your own skin.

Completing an outfit with accessories and footwear when wearing women’s clothes as a man

Selecting Gender-Neutral Accessories

When completing an outfit while wearing women’s clothes as a man, opt for accessories that are more gender-neutral or have masculine elements. Classic accessories like watches, belts, sunglasses, and hats can add an extra touch to any outfit without compromising its overall aesthetic.

Choosing Appropriate Footwear

Footwear is an essential part of any outfit, and it can play a significant role in balancing the femininity of women’s clothes. Stick to gender-neutral or masculine footwear options such as sneakers, loafers, or boots. These styles can complement various outfits while maintaining a cohesive look.

Experimenting with Layered Jewelry

Jewelry can be a great way to add personality and style to your outfit. Experiment with layered necklaces or bracelets that have more neutral designs. Avoid overly delicate or feminine pieces and instead opt for chunkier chains or leather accessories that align with a more masculine aesthetic.

Styling and accessorizing skirts or dresses in an appropriate way for men

Choosing Skirts and Dresses with Masculine Elements

When selecting skirts or dresses to incorporate into your wardrobe as a man, look for styles that have more masculine elements. This could include opting for A-line skirts with minimal patterns, solid-colored maxi skirts, or shirt dresses that resemble button-down shirts. These choices help maintain a balance between femininity and masculinity.

Pairing Skirts and Dresses with Masculine Pieces

To create an appropriate look when wearing skirts or dresses as a man, pair them with masculine pieces like blazers, jackets, or structured shirts. This helps to counterbalance the femininity of the skirt/dress while creating a stylish ensemble. Consider layering a denim jacket over a floral dress or pairing a tailored blazer with a midi skirt.

Accessorizing Skirts and Dresses

Accessorizing is key when styling skirts or dresses as a man. Opt for gender-neutral accessories like belts to define the waistline of your skirt/dress. Additionally, consider adding statement shoes such as boots or brogues to add an extra touch of masculinity to your outfit. Experiment with different accessories to find what works best for your personal style.

Common challenges and concerns when wearing women’s clothes as a man, and how to address them

Fear of Judgment

One common concern when wearing women’s clothes as a man is the fear of judgment from others. It is important to remember that everyone has their own opinions, but ultimately, it is your happiness and comfort that matter. Embrace self-confidence and remind yourself that fashion has no gender boundaries.

Finding the Right Fit

Finding the right fit can be challenging when exploring women’s clothing as a man. Women’s sizing often differs from men’s, so it may require some trial and error to find the perfect fit. Take accurate measurements and refer to size charts provided by retailers. Additionally, consider seeking out brands or stores that offer inclusive sizing options or cater specifically to gender-fluid individuals.

Dealing with Potential Reactions

It is natural to worry about potential reactions from others when wearing women’s clothes as a man. However, it is essential to remember that you are not responsible for other people’s opinions or reactions. Surround yourself with supportive friends and family who accept you for who you are. Over time, you will become more resilient in handling any negative reactions that may arise.

Finding online communities and resources for men interested in wearing women’s clothing

Online Forums and Discussion Boards

There are numerous online communities where men interested in wearing women’s clothing can connect with like-minded individuals. Websites such as Reddit have dedicated subreddits where members share their experiences, seek advice, and provide support for one another. Joining these forums allows you to engage in discussions, ask questions, and gain valuable insights.

Social Media Platforms

Social media platforms like Instagram and Twitter can be excellent resources for finding inspiration and connecting with others who share similar interests. Follow fashion influencers or hashtags related to gender-fluid fashion to discover new styles, outfit ideas, and online communities. Engage with these individuals by commenting on their posts or direct messaging them to build connections.

Online Retailers and Blogs

Many online retailers and fashion blogs cater specifically to men interested in wearing women’s clothing. These platforms often provide styling tips, product recommendations, and personal stories from individuals who have embraced gender-fluid fashion. Explore these websites to expand your knowledge, find new brands, and gain inspiration for your own wardrobe.

Navigating societal expectations and potential reactions while confidently wearing women’s clothes as a man


Navigating societal expectations requires self-acceptance and embracing your own identity. Understand that societal norms are constantly evolving, and it is essential to prioritize your own happiness over conforming to outdated expectations. Embrace the confidence that comes from being true to yourself.

Educate Others through Open Conversations

Addressing potential reactions from others can be challenging but engaging in open conversations can help educate people about gender fluidity and the importance of acceptance. Be prepared to explain your choices calmly and assertively when faced with questions or criticism. Sharing personal experiences can foster understanding and challenge stereotypes.

Build a Supportive Network

Building a supportive network of friends, family, or online communities is crucial when navigating potential reactions while confidently wearing women’s clothes as a man. Surround yourself with individuals who accept you for who you are without judgment. Their support will provide strength during challenging times and reinforce your confidence in expressing yourself authentically.

In conclusion, with an open mindset and a focus on personal style, men can confidently explore and embrace women’s clothing, creating unique and inclusive fashion choices that break traditional gender norms.

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