Crossdressed Outfit of the Week

Crossdressed outfit of the week is where we share the stylish clothes we’ve found that will fit crossdressers with a larger figure. All clothes will be available in at least size 18 (or XL), and shoes at least 11W.

Crossdressed Outfit of the Week: Here Comes The Snow

By Vanessa Law | Published November 7, 2009 | 7 Comments

After a Halloween hiatus, crossdressed outfit of the week is back, and I’ve got some great crossdressing fashion ideas to share with you.  While I dearly love browsing for a cute skirt, or the perfect top to complete my outfit I’m sometimes frustrated with not being able to find my size. Crossdressed Outfit of the Week features clothes that at the time of writing are available in at least size XL (or 16/18) and shoes available in 11W or larger.

Crossdressing in the Snow

Crossdressing fashion: A mid-length skirt

Crossdressing fashion: A mid-length skirt

Fall and Winter fashions are a crossdresser’s dream come true. Gone are the short breezy skirts and skimpy tops that all but scream masculine at your too broad shoulders. One of my fall favorites it the mid-long skirt paired with a good pair of boots. In the fashions shown here the floral skirt (on special at almost $55 off the original price now) has a femininity about it without sporting too small a floral pattern. As you know, small patterns make you look even larger – not something any girl wants ;)

A Crossdressers Favorite: High Heel Boots

A Crossdresser's Favorite: High Heel Boots

I love shoes of all types, but I have a particular fondness for boots. My favorite are ankle boots, though in Northwest winters ankle boots will leave your legs cold and wet. This week’s crossdressed outfit features a stylish mid calf leather boot. I’m trying hard to resist buying this one (I just sent back a pair of boots that didn’t quit fit, but even then my lovely wife is looking at my growing shoe collection with … concern).

Have fun with the last few weeks of fall while the remaining few leaves cling to the trees and the snow is held at bay.

—
P.S. I apologize for being a bit quiet these last few weeks. Between work, family drama and home projects it’s been a bit tricky to do one of the things I love the most – spending time with the lovely ladies at Crossdresser Heaven.


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A Last Chance Halloween Costume

By Vanessa Law | Published October 28, 2009 | 1 Comment

So you’ve ignored all the signs of impending Halloweeness.  You decided not to plan your crossdressing Halloween costume, or to prepare yourself to crossdress as a sexy nurse. You’ve all but given up hope this year. After all, it’s too much work, the costumes are too expensive, and someone may figure out what you’re really up to.

Don’t give up just because the 31st is almost upon you! Here’s three costume ideas that make use of your natural manliness and allow you to crossdress at the same time!

The frumpy housewife

Crossdress as a frumpy housewife

Crossdress as a frumpy housewife

Don’t feel like shaving? Starting to grow a beer belly? No problem, your physique is perfect for our first costume idea – The frumpy housewife. Throw on an old gown and some slippers, and let your five 0’ clock shadow complete your look. If you have long hair you can crank your costume up to the next level with some large rollers, and don’t forget a dab of poorly applied makeup. Noone will ever suggest that you’re trying to achieve feminine perfection, and you’ll save hours on hair and makeup!

The biker Babe (Almost)

Not every biker babe is blessed with a curvaceous body. There are some that ripple muscle or attempt to ripple with too much body cushion. You can use this to your advantage! Just throw on your knee high boots, a pair of jeans and a tight t-shirt. A wind-ruffled wig is all you need to finish off your outfit. You’ll give folks a good laugh, and don’t even need to remove your body hair to do it.

The Transvestite

Last but not least you could choose to go as a slightly sexed up version of you. Your tightest mini-skirt, some deep red lipstick and a sultry strut. If you’ve been crossdressing for a while your wardrobe will probably contain all the necessary items. But watch out! You’ll definitely get questions, and you might even find some people circling dangerously close to your secret.

Even if you don’t decide to crossdress, the most important thing is to go out and have some fun this Halloween! Scare yourself sexy…

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It’s Halloween – Do you Know How To Crossdress?

By Vanessa Law | Published October 21, 2009 | 4 Comments

So I’ll admit it – I go a bit crazy around Halloween. I just can’t help getting excited by the thought that so many crossdressers will be out expressing their true selves in public! It’s almost a crime that so many of us only get to do this once a year, but boy when that times comes around – watch out!

Wear a sexy nurse outfit this Halloween

Wear a sexy nurse outfit this Halloween

As I was writing this post my beautiful wife popped her head in to see what I was doing. She thought it was strange that I would ask you – do you know how to crossdress? Since, most of the readers of Crossdresser Heaven are crossdressers, presumably you would have some idea how to crossdress :) Questioning your ability to dress en femme was not my intention. Rather I wanted to ask – Do you know how to crossdress at Halloween? In some sense it’s easier to crossdress at this time of year, but you can’t rely on everything falling into place at the last minute. A successful Halloween crossdressing adventure requires at least a little bit of planning.

Have you planned your crossdressing escapade?

Do you have your outfit all planned out? Have you coordinated your makeup with your outfit, and checked to make sure you’ve got the perfect earrings to go with it? You can’t just wear any old jewelry with a sexy nurse outfit. Some outfits demand a certain kind of shoe. Whether it’s a spiked stiletto boot or sexy white pump you’ve got to be prepared.

A Halloween Princess

I’ve always wanted to dress up as a princess for Halloween. A princess like in the Disney movies in a flowing ball gown. To dream, if just for one night, that I was a

Crossdress as a princess this year

Crossdress as a princess this year

beautiful damsel living in a tower. With each day filled with sunshine, signing birds and elaborate outfits. If you’re planning to go as a princess, well – that would require a bit of planning. Your jewelry will need to look as expensive as your outfit. This is also the perfect time to try a new updo – it looks extremely sexy when you’re in a formal dress.

So, who are you going to be this year?

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Halloween Is the Crossdressers Time!

By Vanessa Law | Published October 13, 2009 | 1 Comment

You can almost feel the anticipation. It comes but once a year. It’s the time when crossdressers can express their true selves without fear of ridicule. So it’s time to glam up!

Last year at Halloween time I wrote a post describing some of the many crossdresser halloween costumes that men can choose from during this season. I thought this year I’d share some more of my favorite costumes and inspire you to take a bold step out crossdressed this year!

Crossdress as Marilyn Monroe this Halloween

Crossdress as Marilyn Monroe this Halloween

Who doesn’t want to look as glamorous as Marilyn Monroe in her heyday? When you crossdress as Marilyn you’ll get to dress to the nines and show off your flirty side. As an added bonus, you can coordinate this costume with your loved one, who has the choice of many public figures who had steamy relationships with Marilyn.

Cross dress as a naughty school girl this Halloween!

Cross dress as a naughty school girl this Halloween!

After years of trying to convince my wife to go as a sexy school girl, I figure that perhaps she wants me to lead by example :) If you decide to crossdress as a schoolgirl this Halloween, be warned. This costume will require a feminine physique to pull off well. If you’re looking for a school girl costume a bit more forgiving of the male figure, try this still sexy yet less revealing schoolgirl costume.

Halloween Crossdressing Advice

A few things to keep in mind when you’re out crossdressed this Halloween. The most important thing is to have fun! Don’t worry what people will think, everyone is dressed up. Don’t worry about being too feminine – you can just say you’re getting into character. If you’ve nervous of revealing your secret, don’t dress in everyday woman’s clothes! The more backstory you can provide about your costume, the safer you’ll be. Having to explain why you just happen to have the perfect matching blouse and skirt could be…interesting.

Trick or treat!

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Crossdresser Halloween Costumes

By Vanessa Law | Published October 4, 2008 | 16 Comments
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?

—
P.S. For the rest of the year, dress yourself in the latest fashion. Save time and money by buying wholesale clothing online!

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Crossdressed Outfit of the Week – Last Flirt With Summer

By Vanessa Law | Published September 12, 2008 | 1 Comment
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!

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Crossdresser Outfit of the Week – The Return to Fall

By Vanessa Law | Published September 5, 2008 | 1 Comment

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!

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