Styling Tips for Transgender Men in Transition

Finding clothes that both fit well and make us feel comfortable and confident can be a struggle for any body, but this can be especially true for those outside of the cisgender spectrum. Most transgender guys will, especially at the beginning of their transitioning journey, find comfort in their stand-by comfy sweats. Of course, there is absolutely nothing wrong with doing this if that is what makes you feel comfortable and confident moving about in the world. However, there are many ways to dress during this period that can help you feel both comfortable and confident in your masculinity.

If you already naturally have a body shape that is perceived as more masculine, you probably won’t have much trouble finding many styles of men’s clothing that fit well and look good. If your body still has a more feminine shape, however, finding comfortable and well-fitting clothing may present more of a challenge. Luckily, we have this handy style guide here to help you on your journey.

Rock a Plaid Flannel Shirt

Plaid flannel shirts are a classic for many reasons. Soft and comfortable, but always in style, this combination of pattern and thick, soft cotton is ideal for trans guys in transition. This particular pattern, in addition to the natural weight of the flannel fabric, is great for masking curves and creating a more masculine appearance in general.

Opt for Button-downs

Any style or color of men’s button-down shirt can be a great option for transmen, especially during a transition period. Much like a plaid flannel style, a button-down shirt can be a great option for subtly concealing curves. Button-downs are also a great option because they can be worn in almost any conceivable situation. Headed to work? Wear your button-down with some slacks and loafers. Hanging out with friends on the weekend? Throw on a button-down shirt with some jeans and your favorite sneakers. Headed to a wedding? Just wear your button-down under a suit jacket, and you are ready to go.

Watch for Darts

Many tops, especially formal styles, will come with extra seams sewn into the backs or sides. These seams are called darts, and they are meant to accentuate curves and create shape, which can be fine for many people but is probably a style a transitioning trans man will want to avoid, as these seams can create a more feminine outline. If you already own shirts or jackets with darts in them, they can usually be gently removed with a seam ripper.

Get Some Corduroy Shirts

Men’s corduroy shirts, much like flannels and button-downs, are a great way to conceal while remaining both stylish and comfortable. These shirts are also versatile and can easily be dressed up or down. Pair these shirts with a pair of jeans or khaki shirts for a casual look. Alternatively, you can dress these shirts up by tucking them into dress pants for a date night.

Learn to Layer

Strategically layering clothing is a fantastic style technique for the transitioning trans man. Especially if you do not yet have a safe binder, layering clothing can be a stylish and safe way to hide your curves and feel comfortable in your clothes.

Layering with a simple, lightweight jacket, such as a men’s blazer or denim jacket, can really pull together a whole look. The right jacket will give the appearance of having broader shoulders and will help minimize the appearance of hips.

Layering is also a great technique for effectively hiding your chest. Sweatshirts and sweaters are always stand-bys, but even just layering a close-fitting t-shirt under a more loose-fitting button-up can provide the masculine-of-center vibe you are going for.

Vests are Your Friend

Speaking of layering, a well-fitted men’s vest can be a great addition to your look for almost any occasion. When shopping for men’s suits, consider a sleek and stylish vest to wear under your suit jacket. The vest can help conceal curves and also looks incredibly dapper. The same vest can be worn in more casual environments as well, such as paired with jeans for a night out or with more casual slacks for an office-ready work outfit.

Hop on the “Boyfriend”-trend

It may take some trial and error, but find your size in men’s pants and slacks. You may find you want to wear them at the hip instead of at the waist to avoid accentuating curves. Currently, the “boyfriend” cut is very popular. This style of slacks is already a very gender-fluid sort of a look and, therefore, looks great on every body. Boyfriend jeans are meant to be worn slouched and relaxed, which is perfect for anyone trying to subtly conceal curves.

Overall, remember that style tips are just that-tips. These are not hard and fast rules, so take each with a grain of salt. There are no rules in gender or in fashion, after all, so wear whatever makes you feel comfortable and confident.


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