Fit to Flatter Crossdressers

Fit To Flatter

In my past articles I’ve informed you about what types of clothing are best in order to assimilate your female identity. However, one thing I often notice, with really everyone no matter their gender identity, is people aren’t always sure how clothing is designed to fit the body. So, let’s talk about clothing fit.

My very first piece of advice is don’t wear something you don’t love, or that doesn’t fit. It’s not worth the emotional effort!


Let’s begin with the epitome of femininity: the dress. The first thing we need to get out of the way is a dress is a full garment, covering both the upper and lower body; skirts fit differently than dresses, and you may wear a different standard size dress than you would a skirt. With a dress, the seam or strap should sit on the shoulder or the drape of a dazzling designer dress may turn out to look drab. A dress with armholes, should permit full range of motion, and mask your undergarments. If the dress is made well it will align with the hips. A structured waistline is the most difficult to fit, especially on a transitioning body where the natural waistline may be lower than a traditional waistline; so, depending on your shape, an empire waist may be your best friend, but beware - the design line should sit just below your bust line, not on the bust or too far beneath the bust. If you can’t make this work with your cup size or your body shape, move on and don’t look back. A seamstress can alter most shoulder, hip and hemline issues, but waistlines are much less forgiving. The key is to ensure the waist is as flattering as possible, and the best garments for a transitioning body are constructed with a material allowing the body to naturally create the waistline.

Some Empire Waist Style Dresses

If you are using silicone breasts or other breast padding, I advise against selecting strapless dresses or low cut necklines. The risk of the padding showing with movement is too great. The Enticing En Femme Dress, which fully covers the bust line is just as sexy as a strapless silhouette. I also would discourage against selecting cap style, raglan or standard short sleeves. Your best options are sleeveless, dolman or batwing sleeves, and long sleeves, which will all soften the shape of your upper arms and shoulders.

Skirts & Pants

Skirts, like the dress, are a separate staple. Skirts come in a variety of styles and fashion trends. Full skirts and peplum skirts are my personal favorite because they give “insta-hips.” In general, both skirts and pants should sit right at or just below the natural waistline, and the fabric should not pucker or billow with extra fabric, pockets should sit flat while standing and you shouldn’t have any trouble zipping or buttoning the garment. This is an extremely important rule for transgender bodies, as a skirt or pant too tight or loose through the front may draw undesirable attention to the crotch.

I always find the most difficult part is deciding on the length of pants, which is duly determined by the height of your shoes and the style. (Check out the En Femme Pants conversion guide article if you are interested in pants and how best to choose a style). As for the hem of a dress, skirt or dress pant, it should graze the floor, but never fully drag on the ground.

As with dresses, hemlines are easy to correct, but unlike dresses, the waist of skirts and pants can easily be tailored. You can also have pockets sewn shut, the legs and crotches of pants slimmed, and skirt seams let out to perfect a fashion piece.

Jackets, Blazers & Button Down Blouses

If you’re a professional gal, you’ll probably be working out a blouse with a suit jacket or blazer at some point. In men’s wear there are tons of rules about the fit of shirts and jackets, but women’s wear is much more relaxed in those rules. However, here’s the caution: you already have large shoulders, and the slightest imperfection in the shoulder area can have you misconstrued for an NFL linebacker. Like a dress, the shoulder seam should, and in this case must, sit right on the shoulder, without being too roomy, and without pulling or restricting your arms or range of motion. Shoulder pads should be restricted to smaller body frames.

With button down blouses, you’ll want to ensure there is no gaping in the bust area, and the hip area, called the sweep, isn’t too tight, which may cause it to ride up when you walk around. You can check this by walking around the dressing room with the blouse tucked into skirt or pants. A tailor cannot easily correct the spacing between buttons or the shoulder seam areas in a jacket or blouse; so, before buying, make sure these fit to a “T” for your t-girl body.

Beyond these rules, you’re options are nearly limitless. You have the ability to wear jackets and blazers cut long or cropped at the waist, like the En Femme Modern Jacket; cut tight or loose at the waist; and those you never button or zip, which is great if your bust line is very full. Sleeve length in both jackets and blouses is also a personal preference, but you will never want too much sleeve showing beyond the cuff of the jacket.


You can probably guess that if you’re pre-op, swimwear is an automatic challenge, and rather limiting in selection. There are companies specializing in transgender swimwear, which include well concealed pockets for prosthetic breasts and body padding, but if you need a more immediate option, the best tip I can provide is selecting a full body suit that includes a skirt panel. You tend to see this style on “old people;” HOWEVER, this doesn’t mean you can’t find them in fashion forward patterns or styles.

An alternative to the dress style swimsuit is a tankini with matching boy short, and while you may shudder at wearing anything remotely masculine, this style provides ample coverage for your body and any waterproof body padding you may be using. Remember, if your swimwear doesn’t include the prosthetic pockets, you’ll want to use waterproof body glue for your silicone breasts.


I want to briefly mention one accessory you’ll most likely always have with you, a handbag. Because handbags are available in a massive variety of styles, sizes, and shapes, it can be overwhelming choosing the best bag for your shape.

If you’re tall and thin, select handbags wider than they are tall; slouchy shapes like the hobo are best, but avoid shoulder bags with short straps as they will make you look even taller. Smaller frame ladies should select a medium size bag instead an oversized bag, but avoid shoulder bags with a long strap, which will weigh you down and make you look shorter. For those larger than life, choose a large structured or boxy bag to balance out your curves; a bag too small can make you look larger, and choose bold prints over tiny prints. One handbag for all frames, as long as they are proportional, is a clutch - it’s why it’s considered a classic.

As with all the articles I contribute to En Femme, my goal with these guidelines is providing the tools you’ll be able to use to transition. I know the emotional, physical, and legal process isn’t as simple as picking up a few make-up and fashion tips from a handful of online writings, but I do hope the information I’m able to provide is useful in creating the woman and identity you want to portray.