The question we all ask ourselves, “What should I wear?” We ask this question if we are planning to go shopping, attend a local CD event, or just enjoy a fun day dressing at home. Making a decision of what to wear  can be complicated and sometimes daunting. When I go out in public, I want to be representative of a woman enjoying the day out shopping or an evening with friends. No matter what the event or plan,  I question myself, “is everything in place? is my makeup too glam? does my outfit blend with the day and season?”

 

I want this moment of my crossdressing to go smoothly and be fun. For many of us, if we are dressing up at home,  we can pick any theme we want and have some fun. I know because I have strutted along the imaginary red carpet in the hallway to the applause of the crowd, the adulation of the audience,  the flashing of cameras in my red gown while it’s the middle of summer.  I do think it is important  if you are planning to post your photos to CDH or other sites, that you try to dress for the social calendar. Why? I think you’ll feel more connected to what is currently happening even if you can’t go out and meet up with your CD friends.

 

A perfect example is the Holidays!! The holiday season is coming up and maybe you can put some time on the calendar to enjoy getting all glammed for a holiday season photo session.  It could be planning on an outfit for a Holiday cocktail party, Holiday dinner party, Holiday office party or Holiday Date Night with someone special. I recently did this for a summer photo session. I planned out my dress, makeup, hair and all the accessories ahead of time for a Garden Party photo session.  It was so much fun planning out an outfit with a theme in mind. We have all  heard your wife or girlfriend say, “I need a new dress” for a special upcoming event.

 

I definitely have the holiday season on my mind. I am planning to buy a new dress and have one on my favorite list if it drops to 50% off. For me, a Holiday dress must have sequins or sparkle, be form fitting enhancing my hips, long sleeves and a v neckline. My hair, I’ll stick with my brunette wig with blonde highlights. My makeup will be a smokey eye with a matte red lip 👄. Shoes, no question, my go to black patent 4 1/2 stilettos! I  am considering some silver rhinestone pumps and a cocktail dress to set off these statement heels!

 

With my outer fashion decision made, I want my lingerie to compliment my dress. The holiday season brings so much new lingerie to retailers. I expect to pick out a new bra and panties in black with a little holiday colored lace trim. I am a die hard ” garter belt girl”  and will pair with sheer night shade black stockings with a shine to them. I generally use shapewear with a dress. I have a black slip which slims my waist, lifts my bum and bust. Accessories can make the outfit. I am planning on a silver necklace with black stones, dangling silver earrings and 4 silver rings. Finally, a silver  wrist bracelet and matching silver jewel purse. The crowning touch is press on nails with white and silver details.

 

It’s a plan which could change depending on what dress I purchase but I have the foundation in place –  I know, my hair, accessories, makeup and heels can work with a similar sequin sparkle dresses if I can’t acquire the dress on my fav list. Like many of you, I have three LBD’s in the closet just in case. I find it is important to be prepared because it saves time when your day comes about. You’re not second guessing yourself and questioning yourself when standing in front of the mirror, “Maybe plum or mauve eyeshadow, midi dress or mini, are these the right shoes?” If this happens, there is a chance of having your look go sideways and spoiling your crossdressing time.

 

Be committed to making a list if this is needed. I have dressed up a few times in the past where I was thinking about three different dresses. Make sure your choice match your coloring and make up. The process can be daunting, but if you prepare for the day you’ll find much enjoyment and less stress. Plus, the woman you see in the mirror will be the one you expect to see, looking fabulous!

 

 

 

 

 

 

More Articles by Melissa Honey

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Bluest Belladonna
Baroness
Active Member
3 months ago

Dear Melissa, I am am honored to be the first to comment. I would love to express my adoration for your article! The one distinct element which I found natural in cross dressing was the process of planning and preparing for a calendar theme. I was fascinated as a child, knowing women would spend days preparing to go out. From buying or hand sewing the garments, to the makeup preparation, the hair styles, the endless number of accessories and even the “hidden" details such as making sure the lingerie matched. Melissa, I do have one request, may we see a… Read more »

Lea
Lady
Trusted Member
2 months ago

I enjoyed reading your article Melissa because there were so many things you had mentioned that were exactly relevant to me. I used to waste a good 30 minutes of free time for venturing out with figuring my outfit. On days I’m planning on going dressed somewhere, I try to think about my outfit choice earlier that day or even when falling asleep the previous night. This lets me maximize my being out dressed time. I use themes sometimes for dress up sessions at home. Several times I did go with a current theme, like Super Bowl Sunday, Valentine’s Day,… Read more »

Franziska Frankfurt
Duchess
Trusted Member
2 months ago

Dear Melissa, Thanks for your wonderful and inspiring article. Love, Franzi

Josie Jones
Lady
Active Member
2 months ago

A great article and plan. I just decorated the Christmas tree and have been thinking about a Christmas Card photo for my friends at CDH. I haven’t exactly settled on my outfit (black and sparkly, red and Christmasy) but your article hits all the right points. I’m looking forward to the upcoming photos from our sisters!

Patie Kay
Lady
Member
2 months ago

Melissa, loved your article. It does take some time and thought into what you wear per event. I always try to fit into where ever I go dressed, clubing, shopping or just a walk around. However, I do real enjoy dressing for the evening out. Hugs!

Kris Burton
Lady
Trusted Member
2 months ago

Great article Melissa – and well timed! I currently did two photo sessions with a Christmas theme using two different outfits. Doing so gave em some ideas for future sessions with seasonal themes to take on a more artistic approach – and enhancing the overall fun! It’s good to see we are thinking along the same lines.

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