Shopping for Women's Clothes as a Crossdresser
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Now for the good part. The pinnacle of being a crossdresser for me is dressing up like a woman and going out to shop. I love nothing more than to spend a few hours shopping as a woman whether it's stocking up on groceries or scooping up a handful of items and locking myself away in the safety of a dressing room. Regardless of the errand, dressing up like a woman and venturing out into public is the biggest reward a cross dresser can give herself, and I can tell you from personal experience, the more you shop dressed as a woman, the easier it gets. Here is some advice that I would give based on personal experience.
- Fit in with the crowd. If you want to be discreet and invite as few looks from others as possible, then you must fit in with the crowd. Determine what time you want to venture out, and then match your outfit to what the majority of women are wearing at that time. There is always a time of day and scenario that will accommodate your shopping while crossdressed, so plan ahead and don't be disappointed if you can't always wear a skirt.
If you must wear a skirt and pantyhose out in public, keep the outfit casual and conservative because how often do you see a woman shopping in a short dress, nylons, and 4" heels.
Early morning to about 9:30 AM: This is actually one of my favorite times to shop as a cross dresser. The crowds are miniscule and you have the option of dressing up like a woman on her way into work (which means you can wear a skirt and pantyhose), a woman running to the grocery store for a gallon of milk, or a woman getting an early start on her day of shopping. If you dress casually in the morning meaning a pair of jeans, pull your hair back into a ponytail, wear less makeup, and wear fewer accessories.
The picture at left is a perfect example of how I often dress when I want
to blend in
with the crowd...and I'm still managing to wear pantyhose with
a skirt. The difference is that my skirt and cami are casual garments from Aeropostale, and my pantyhose are a subtle nude shade. If you are a woman on her way into work, look the part with good makeup, nice hair, and more accessories like a flashy pair of earrings. One other trick that I use when posing as working woman is I've taken an old work badge and laminated a picture of me dolled up over the original picture, so I can wear it around my neck or attach it to the side of my skirt.
9:30 AM to 4:30 PM: This is a more difficult time to cross dress in public. The majority of people out and about are mothers who have just sent the kids to school and are out running errands or shopping for themselves, and we know how much we girls like to scrutinize other girls, so you're more likely to get glances from those around you during this time. If you cross dress during the day in public, you have to dress casually (which usually means no skirt) with the one exception being a working girl who is on her
lunch break...a challenging but rewarding scenario if you can pull it off.
4:30 to 7:00 PM: This is a difficult time to cross dress in public because the crowds are likely peaking at this time of day, and it's nearly impossible to be out and about and not get noticed. There are some veteran girls out there who can pull it off any time of day, but for the beginner, I would not recommend shopping or venturing out in public cross dressed during this time. Perhaps a quick run into a grocery store or other store dressed as a working girl on her way home could be done, but it's easier to do this a little bit later.
7:00 PM to Store closing: This is a more relaxing time to head out for a few hours of cross dressing because the crowds are thin and you also have the cover of night. Night time shouldn't make a difference, but I believe it does to a girl's confidence, and since confidence is key, anything that makes you more relaxed is better. You can still pull off the working girl scenario at this hour (the badge helps :-), or you can choose to go casual. A lot of women out at this time have dressed into a jogging suit or other clothing that is comfortable to lounge in during these hours. Heavier make-up is acceptable because you would expect that from a woman near the end of the day. Most of my clothing shopping is done during the day when the crowds are smaller with my grocery shopping done in the evening.
Pictured at right is something that I wore to Costco around 11 AM giving the appearance of a woman who has dressed casually with sunglasses perched on my head as an accessory.
Tips and Advice
Hiding your stash
Ways to start
Reasons to crossdress
Talking to your SO