Dressing as a Woman for Halloween – Outfit Ideas 2023

Halloween is just around the corner, and you still don't know what to dress up as? Or maybe you do know, but you're not sure whether you should actually go through with it?

There are endless (mostly terrible) Halloween costumes out there. Some people even try to pass off "I'm not wearing a costume" as a genuine costume. And let's not forget those oh-so-hilarious full-body costumes, which frankly belong at the very bottom of the costume barrel.

But this post is about my thoughts on one particular topic: a man dressing as a woman for Halloween.

I want to keep this post updated with my favorite outfits, along with the matching product links (all affiliate links) and descriptions.

Why would I even do this?

As always, the real question is: why not? Though that one isn't quite so easy to answer here.

Halloween comes with a pretty fixed theme built in: being scary. Anything within that spooky context is fair game — from the classic zombie to the witch, pretty much anything goes. That said, some people treat Halloween more like a substitute for Carnival and dress up as literally anything. But the general tone should still lean spooky.

Which means a plain "woman" outfit doesn't entirely fit the theme, even though I completely understand and share the wish to dress up that way. If all you care about is getting dressed and done up as a woman, then just do it! But if the "Halloween" part matters to you too, I've got some inspiration for how you could approach it.

I'm curious how you see it yourself — feel free to share your thoughts in the comments. I'd love to hear them.

Have fun!

Ideas for how it can still work

Some people claim Halloween just isn't the right occasion to dress as a woman. And I partly agree. A man with a taste for pumps, glam, and makeup won't exactly stand out at Carnival, since basically everyone is doing the same thing there: dressing as a woman. At Halloween, of course, that's a very different story.

If sideways looks don't bother you at all, you can of course just show up in a blouse and skirt, or a dress and heels. But (!) I think Halloween actually leaves a lot more room for creativity in choosing your outfit.

Because there's something genuinely appealing about a man stepping into the feminine side of fashion while flipping the script at the same time. What do I mean by that? Stay true to the theme, but shop in the women's section anyway.

In this post, which I'll keep expanding every year with new outfit tips and experiences, let me introduce you to my absolute favorites.

Vampirina 🧛‍♀️

Tip: vampire costume — https://amzn.to/3gWb9Dj

How about going as a Vampirina this year, for instance? The prep is simple. Red nail polish and a blood-smeared face, paired with a red-haired (https://amzn.to/3Nk09vw) or black wig and bold red lipstick, already gets you the basics down. At that point, people probably won't recognize you — they'll be too busy shuddering.

And depending on how confident you are on your feet, you can really go all out with the footwear too. Glide across the dance floor in dizzyingly high red lace-up patent heels (https://amzn.to/3DnNMtA) — or slip into something a bit more stable, like ankle boots, if the night's going to be a long one.

And of course, it's all about the details! If, like me, you don't have pierced ears, your options get a bit more limited — but these spider earrings (https://amzn.to/3U5lpY0) still dress up the outfit brilliantly.

I was incredibly excited for the evening the first time I got to wear and actually go out in this costume, because I genuinely didn't know how it would land. Partly because of the slightly risqué outfit itself, and partly because of the whole idea of a man showing up at Halloween in a feminine costume.

Since it was a small, private, but genuinely nice party, the setting felt a bit more protected.

And what can I say? In the photos we show friends and acquaintances, nobody recognizes me. You genuinely can't tell there's a man in the costume instead of a woman. And the outfit itself is just absolutely hot — in the good sense. But you should also know: it's hot in the other sense too. Long hair covering your shoulders, and dress fabric that's usually polyester — not exactly breathable.

Harlequin costume

For Halloween 2022, I tried a slightly bolder outfit. It's more revealing, mostly because it just isn't unbearably warm to wear. But it's all the hotter for it! What is it? A short harlequin dress!

I paired it with fishnet tights, so my legs weren't left mostly bare. The costume also gets a bit risqué when you sit down, so wearing tights underneath the harlequin knee socks makes it just perfect.

Black pumps or closed ankle boots work great with it. You can find where to buy pumps and ankle boots in larger sizes in my shoe guide. If you'd like a bit more stability underfoot — since there's usually drinking involved at Halloween parties — go for ankle boots instead. My clear recommendation here is ankle boots by Tamaris. They come in size 42, and some styles even in 43. They don't just look good, they're also incredibly comfortable — which they really should be, for a long night out.

I'd also recommend a pair of fine lace mesh gloves — they round off the outfit perfectly.

Experiences: a man dressing as a woman for Halloween 🎃

Sure, for some people it might seem spooky in itself that a man dresses as a woman for Halloween. But strictly speaking, you're dressing as a Vampirina, a witch, or some other eerie figure. A plain "as a woman" costume, with no spooky theme, would really be more of a Carnival thing.

This year is going to be especially exciting, because for the first time the party won't just be private guests — it's moving outdoors too. I'll report back 🙂

What do you think of the idea of buying feminine costumes for Halloween and really shining in them? Have you tried it yourself? I'd love to read your comment!