Archive for the ‘Crossdressed Outfit of the Week’ Category

October 04 2008 6 Comments

Crossdresser Halloween Costumes

Sexy Pirate Costume

Sexy Pirate Costume

Our favorite holiday is almost upon us! The day where we can dress to the nines in sexy skirts, high heels and stockings without fear that we’ll be outed. That’s right, Halloween is almost here, and crossdressers across the world will be using this as an opportunity to express their femininity to the world in a safe and fun way.

One of my favorite costumes so far has been as a Vegas-themed hooker. I got to wear a sexy outfit and high heels to a friend’s party. I thoroughly enjoyed myself, and I must have done a good job dressing up, because it took them a while to recognize me. Later on in the evening I got a few questions about who had done my makeup. This was followed by them hastily covering a look of surprise when I mentioned that the work of over-done lady of the night art was all my own. Surprisingly, I enjoyed the sense of near discovery as well.

Have you picked out your Crossdresser Halloween Costume?

If not, what are you waiting for? There are an abundance of costumes to choose from, such as this sexy pirate costume, and thanks to McDonalds it’s easier than ever to find a plus sized woman’s costume that will fit you. Most of the online stores offer easy refunds so if you;’re a bit shy still you don’t need to walk into a store and buy a woman’s costume.

Sex Plus Sized Costume

Sex Plus Sized Costume

Many of you are veteran’s, and have used many a halloween for transgender revelry. For those who are still new at this, I’ve got a few tips on how to make the most of your halloween holiday:

Crossdressing Halloween Tips

  • Use the opportunity to get into character and practice your feminine movement and speaking. Everyone will laugh, and you’ll get a chance to be a lady in front of other people.
  • Your makeup doesn’t need to be perfect. In fact, the better it is, the more chance there is that someone will suspect something. Not that you shouldn’t do your best, just don’t be stressed if your lip liner isn’t 100% perfect.
  • If it’s your first time and you’re nervous about being outed, wear a woman’s costume. It’s a lot easier to pretend you do this once a year if you’re not wearing your best clothes and jewelry.
  • Go with a friend and make a theme of it. It’s a lot of fun if both you and your wife or girlfriend are crossdressing.
  • Have fun! It’ll be hard to relax, with the adrenaline running through your body. Use it to enjoy the evening - be outgoing and get involved.
Crossdresser Halloween Costume - Have you been a good girl?

Let me know, I’d love to hear your stories about crossdressing at halloween. What outfit did you wear? Did anyone guess that you dressed up more often than once a year?

September 12 2008 No Comment

Crossdressed Outfit of the Week - Last Flirt With Summer

Flirty transgender dress

Flirty summer dress

Just as I prepare for the cooling dance into fall mother nature decides to give us a week of glorious eighty degree weather! To celebrate this week’s crossdressed outfit is a flirty dress perfect for the final warm days of summer, pair with sensible yet feminine open toed sandals. It’s a great dress for a warm day or paired with some jewelry and heels for semi-formal evening wear.

Sensible, yet feminine sandals

The sandals are great for the taller girls, the lack of heel means that you won’t be towering over everyone else. Be careful though, opened shoes can sometimes make your feet look larger (not a good thing for your average crossdresser). Make sure you get the wide width shoes if your feet are a bit larger.

As always, crossdressed outfit of the week only recommends clothes that are available in at least size 16/18 or XL, with a shoe size of at least 11. We get frustrated with all the gorgeous outfits that won’t fit us so you don’t have to!

I hope you’re making the most of these last few days of warm sunlight.


P.S. Breastforms are great for those covered up months in winter and fall, but it’s hard to look feminine in the hot summer months without breasts of your own. Grow transgender breasts naturally with this revolutionary guide!

September 05 2008 No Comment

Crossdresser Outfit of the Week - The Return to Fall

Crossdressed Outfit of the week has been on hiatus the last few months, but it’s back! The crossdressed outfit of the week is a stylish outfit select especially for crossdressers and the transgender. All blouses, pants, skirts and dresses are available in at least extra large or size 18 at the time of writing. All shoes are available in at least a size 11. So you don’t need to be disappointed by yet another gorgeous outfit that doesn’t fit.

 crossdresser blouseThe crossdressed outfit of the week is a homage to the return of fall. With a sexy Jacquard Blouse that will look great and keep the chill at arm’s length for a few more weeks. It’s on special now for $29, that’s $10 off the regular price!

crossdresser skirtYour blouse will be beautifully complemented with the high waist trumpet skirt, also on special with a savings of more than $20 off the regular price!

Finish off your look with these ultra comfortable low heel ankle boots. transgender boots

Have fun this fall and look fabulous!


P.S. Fashion is a great way to express your femininity, but there’s more to passing than just wearing women’s clothes. Follow this guide to exude feminine grace!

March 07 2008 No Comment

Crossdressed Outfit of the week: Looking forward to spring!

Spring is just around the corner, and we get to set out clocks ahead an hour this weekend to enjoy another scrumptious hour of sunshine! To celebrate the coming of spring, this week’s outfit features strappy sandals, a fun print skirt and a sexy rhinestone tank top. Not only will you start off feeling cool and refreshed for Spring, but you’ll save almost $70!

Match it with some pink lipstick and you’re ready for the sunshine. As always, the crossdressed outfit of the week is chosen with care, and sizes are available up to XL (or size 18), with shoes in sizes up to at least 11W

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Dyeables Flamingo (Women's) - White Satin

February 15 2008 No Comment

Crossdressed Outfit of the week: Shake your booty

Every Friday we bring you the Crossdressed outfit of the week. During the week we hunt down stylish clothes that will fit those of us who aren’t blessed with a petite feminine figure. This means that all clothes will be available in size 18 (or XL), and all shoes will be available sizes up to 11 W.

This week’s fashion theme will emphasize the glorious booty God gave you. ShapeFX jeans from Newport News will lift and shape your rear, while the fashionable Magdesian ankle boots will give a sexy sway to your walk. We finish the look today with a deep V-neck surplice top, also from Newport News.

Look sexy this weekend!

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February 08 2008 No Comment

Crossdressed Outfit of the week: Conservative trendy

I’m starting a new feature here at http://www.crossdresserheaven.com called the Crossdressed outfit of the week. Every Friday I’ll put together an outfit that will not only look fabulous, but actually fit those of us whose proportions are somewhat larger than the typical woman.  All shoes will be available in at least 11W, and clothes will be available in size 18-20, or extra large.

This week’s outfit matches a conservative white embroidered poet sleeve tunic shirt with an olive detail skirt and brown leather 2 inch pumps. The detail on the skirt will add some flare to your conservative look. The outfit will be well complemented by a wide belt, and tan pantyhose.

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Women's RogersAvenue Embroidered Poet Sleeve Tunic Shirt Womens Plus Size