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How I Find Dresses That Work

October 22, 2020


Recently, I bought a dress in a small, mom & pop boutique. It is tricky to buy a dress for a tall or oddly shaped body. I fit in both categories. I am 6 feet 3 inches tall (1.9m) and I have broad shoulders and narrow hips. “It’s hard to buy clothes because I have my father’s hips.” I had to remember all of the things I have learned about dress buying. I decided to record my knowledge here. Maybe this will be useful to someone else!


The neck opening needs to be more narrow for me. It can be larger than a T-shirt opening. There is a limit to how large I will go. This alone makes dress shopping difficult because so many dresses show off so much chest and back.

I have body hair. I shave down my front and back some, but a man can only shave so far! Also, wide neck openings feel wrong. I do not know how women do it. I feel ridiculously exposed if the neck opens too largely. I do not want to look like Khalid Shaikh Mohammed in his arrest photo.


The sleeves need to be basic and at least short-sleeve length or longer for me. Since I present male when I wear a dress, transitions matter. Starting with pretty, soft fabric and proceeding to the upper half of my farmer’s-tanned [bulging with muscles] man arm is too abrupt of a transition.

I never wear cap sleeves, bell sleeves, open shoulders, or anything with ruffles. I always wear straight, plain sleeves. It works for me!

No Bust

Since I am a man, and my chest is flat, I try to buy dresses cut for a woman with a small bust. That is a challenge. If extra fabric is available for chest curves, then the dress will never fit right on me.

This adds another dynamic. Having a bust changes how a dress hangs on a body. Not having a bust makes the dress look quite different. It is more form fitting below the bust line. Fabric draping off of a feminine chest covers up belly fat better than the fabric that hangs off of my flat chest!

Non-Feminine Print or Cut

I am a man in a dress. I try to maintain my masculinity. (I know that is confusing…) Also, transitions matter to me. I try to avoid having a print on my dresses and tops that will not make sense near my man-head. I avoid flowers, lace, frills, and bows in general. I avoid exposed skin, such as exposed backs, or cold shoulders as well. If I wear more plain designs near my head, it makes more sense. I look more like a dressy man than like a dude in the wrong clothes, I think.

Skirt Shape

This is not a hard rule. I *try* to stick with pencil shapes instead of flowing skirts/dresses. I think a man wearing an apron or a towel looks good. (I remember thinking this when I was a teenager working in a restaurant. I was wearing an apron, and it did not look girly like a skirt. It even looked kind of good on me. It looked tough and strong.) Likewise, a towel on a man is very manly. Straight lines are better in my eyes.

Sufficient Length

I have mixed motivations here. I do not want to look fetishistic. Therefore, I wear skirts and dresses that come to my knees or lower. I also do not want my skirt to ride up and expose my control tops!! Therefore, I test a dress to make sure it passes the “sit-down test” and the “bend-over test”. There is an additional test that is not just about dress length. The “raised-arms test” verifies that the upper part of the dress will let me raise my arms without showing off too much of my legs (or show off my slip).

No Waist Line

Since I am so tall, I have to pay attention to the waist line. If a dress has one, it probably is going to be in my rib cage. Then the cut of the dress changes. I have to avoid dresses with a waist line almost every time. I hold out hope that I will find a dress in a tall size that will offer me a waist line one day…


Since my shoulders are broader than my hips, dresses often look too big on me in the bottom half. I have had a couple of dresses professionally altered. It made a world of difference! Also, it was fun standing in the seamstress’ shop wearing my dress while she pinned me up. I even took a six-week sewing class (while wearing a skirt) to learn how to alter my own clothes. These days, I alter my own clothes. This has made a huge difference in how good my clothes look on me.

Cleaning Restrictions

This one, I sometimes forget. I try to check the label. I do not want to buy any “dry clean-only” dresses. Furthermore, it is really complicated buying “lay flat to dry” dresses. My children do not know about my crossdressing. I have to schedule when I wash my pretty clothes so that they do not see me folding them, etc. It is most convenient when a dress has “tumble dry” on the label. If I have to choose between two garments in a shop, the label has occasionally made the decision for me!


I hope this is helpful to someone. If you have good ideas that have helped you purchase dresses or anything else, please comment below and teach me or anyone else who reads this.


From → True Stories

  1. Great article Joey 👍. It’s interesting to read what and why you like the style you wear.
    I like drop waist style dresses, preferring midi length. If I wear a dress with a waist, then a foundation garment is a must. (Partly as they feel nice to wear and also for the figure)

  2. David permalink

    Great article Joey. Please tell me you’re shaving at least a little more than the Shaikh. : )

    • 🙂 When I shave my face and neck, I shave down a few inches onto my chest. If I didn’t I would look a little like him. I am thankful that I’m not THAT hairy.

  3. David permalink

    More about that neckline. Its funny, even my wife doesn’t like those big wide open necks. I always thought it was kind of a good look and would buy something with that kind of neck opening for her occasionally. When I started buying for myself, it became very apparent that it’s not a good look for everyone. Clearly, it helps to have the cleavage to go with it. But even those tops with an open but less dramatic “swoop”, seem somehow lacking. I am of the opinion that just a little bit of bling around the neck would help. Doesn’t need to be overtly feminine, just something with a little glint to it to fill in that space and give the neck line some finish. To get away from those big open necklines, I also have been tending to tops that have a traditional collar with lapels. The women’s blouses that have that sort of collar still retain their softness and feminine cut. A nice kind of in-between that feels pretty without feeling awkward.

    Sleeves. I agree, with a man’s wider shoulders, a good fit is hard to find. Not only style, but the arm opening itself tends to be too tight. That’s probably something you can fix with your alteration skills, but way beyond my capabilities. So I tend to go larger when considering sleeves. I am really fond of 3/4 length sleeves which seems pretty common in women’s wear. I never cared for the feel of long sleeves in my man shirts and would always push them up my arms anyway. The 3/4 length feels more natural and comfortable to me.

    I don’t mind tank tops or articles with spaghetti straps. Mostly for around the house so only my spouse can appreciate those bulging muscles you speak of. I’m sure you could pull off the sleeveless look especially with your penchant for cardigans. Layering in general is a really nice fashion practice and for men in pretty clothes it can be especially helpful in achieving a stylish look.

    No bust. Yeah, that’s kind of out there for the whole world to see. Again, layering helps cover what nature omitted. Thats also why I more often wear a skirt and blouse rather than a dress, per se. I think its easier to have the pretty look you’re after by wearing two pieces rather than the one piece of a dress. In my experience, a dress essentially hanging from the shoulders will unhappily show off a lot of areas that just don’t seem to fit well. But your skill with the sewing machine probably cures most of those.

    Feminine prints and cuts. I wouldn’t swear off all of those. I think you can find some beautiful pieces with a bit of flair that still seem just right. For instance, I’ve got this wonderful blouse with a kind of built in scarf around the neck. It hangs down from a single loose knot and feels dressy and very feminine without being over the top. Floral prints too. The right pattern and colors can still work for a man. I certainly get the caution with frills, bows and lace though. I’m happy to save that for the under garments.

    Conclusion. I think I’ll stop right here. Trust me. There is no way I could teach you much Joey. I’ve learned more from your blog than I could ever give back. Thanks for providing a forum to share.

    Stay well,

  4. Gary permalink

    Thanks for the informative observation of dress variations. I guess I am fortunate in that my male dimensions are 5 foot 6 inches tall with a bust of 37 waist 33 and hips 39. I find a size 10 usually fits me well and size 9 wide women’s shoes. I have on many occasions found the pants for men are too tight in the hips and too loose in the waist but some pants for women fit much better. I do not wear a dress or skirt in public, but who knows maybe social norms might change later. I do have many pairs of jeans in a women size as well as some mock turtle shirts that fit me without alteration. Thanks for your blog which I find most interesting.

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