On a forum I belong to someone was looking for clever ways of dressing to conceal the fact that you’re a man in dress. Here’s some of my thoughts on how to do this.

First off, let me point out that woman aren’t born knowing this stuff, they learn it, which means we can too. I learned from watching “What Not to Wear” (which shows that women definitely aren’t born knowing how to dress stylishly), as well as Suzan Nanfeldt’s excellent book “Plus Style,” which intended for plus-sized women. It’s out of print, but usually available on Amazon for about $30-40 and is money extremely well-spent. There’s also lots of info available online if you go looking.

Let’s start by dispelling a myth—black isn’t slimming, tailoring is slimming. OK, that’s a bit of hyperbole. Dark colors do help make things appear smaller. But a big mistake plus-size women make is to wear stuff that’s baggy, which makes them look ever bigger. Whereas something that’s nicely fitted—not skin tight, will actually make you look slimmer. BTW, this also works well for male clothing too. It is scary to do initially, since you think it’s going to show off all the places you’d prefer to hid, but trust me, it actually looks much better if done right. Of course, there’s places where you strategically want some loose fabric—one of the great things about wrap tops is that bunched fabric near the waist is great for camouflaging a bit of stomach flab. But this illusion works in large part because the rest of the garment is fitted, so it doesn’t appear as if you’re trying to hide something.

Let’s dissect a “dressy casual” outfit I typically on outings to nicer places.
I’ve actually got broad shoulders and a short, thick neck. So I usually try to wear V-necked tops, which both makes the neck look longer (and therefore slimmer) and the V-neck also pulls the eye inward, minimizing the shoulders. I also usually wear a pendant necklace, which draws the eye down and away from the neck. Since the abalone sequins on my black knit top are pretty dramatic, I wear a small, subdued pendant, so it wouldn’t fight with the top.

My leather jacket has a bit of princess seaming which tends to be slimming. Also since the jacket was unzipped, it created a vertical line, which lengthens you and again is slimming. I’m six feet in 2” heels, but there’s a number of women of equal height, so I don’t worry about it.

Most of the time out in public I’ll wear pants unless it’s a transgender event. I know, the horror… the horror… but the fact of the matter is women wear pants most of the time, particularly in the San Francisco where it’s usually cool and often foggy or windy. Wearing a dress or skirt in that weather will make you stand out regardless of what sex you are. So I wear a chocolate brown pant with stripes. The low contrast between the brown pants and the black top helps create a seamless line, which again can be slimming. On the other hand, one can also use contrast intentionally. For example, a dark top and light pants or skirt, will make your bottom half look larger. Which is why many women avoid this, but part of the secret is learning how to intentionally break “the rules” since our bodies are built differently that women. The stripe in the pants actually isn’t a good idea if you’ve got a big butt, because the lines emphasize the curve. Which is exactly what I’m trying to do. The pocket on the back of the pants, also emphasizes the size of the butt. Admittedly, wearing my Veronica 2 hip pads help a lot. (Glamour Boutique’s Sweet Cheeks pads, are a good, less costly alternative, since like the Veronica 2, it uses a single pad that wraps around each hip/butt check and avoids the lumpy look of other products that use four pads. The trade-off is that unlike the Veronica 2, the Sweet Cheeks aren’t custom fit.)
My boots are relatively narrow, at least compared to my male shoes, but I also chose a pant with a bit of a flared leg, which makes the boot look smaller in comparison. (Flared sleeves on a shirt create the same optical illusion, making your hands look smaller.)

As far as hands, mine are slim-fingered, but still pretty large. So I generally avoid bracelets and lot of jewelry, which draws attention. But it does help to “scale up” the size of jewelry to look proportionate. So I’ve got one ring that’s got a large stone (about an inch long) on it. Likewise, I’ve got a man’s watch that I actually bought for guy-wear, but was a bit too small (the face is 1” and the watch itself is quite slim, similar to the Skagen watches). However, it ended up looking just right for femme wear. When I wear polish, I wear a light color that doesn’t draw the eye too much and since it blends with my skin color, it lengthens the fingers, which narrows the perceived width of my hands.

My face is broad—even for a guy—so I choose a wig that curls inward a bit at the sides, which narrows the face. I also choose one with some chunked highlights, which makes it look more “natural” than a mono-colored wig. Switching to a longer style also looks more feminine, although you don’t want to go too long and you should be aware of the length that women your age wear (often women tend to go shorter as they get older, but it’s not a hard and fast rule).

In summary, much of learning what to wear is just learning to how to use the illusions that clothing can create.