One of the frequent topics on crossdressing forums is blending and another is dressing in an age-appropriate fashion.
My thoughts on the subject can be summed up as follows: I’m already not supposed to be women’s clothes, so why should I care if i wear something that is supposedly inappropriate for my age?
It’s probably been five years since my GG friend Renee challenged me to expand my comfort zones. That day, I walked into a Windsor store (aimed at teens and those in their twenties) and walked out with a strappy halter dress that is now one of my summer favorites. I thought it looked good and my physique (I spend lots of hours exercising to achieve that physique) suited the look. That wasn’t the only catalyst, but it was a start.
I then started looking at juniors dresses, especially those on sale at Macy’s. I never went to prom (guy nor girl), but why not try on a prom (type) dress and see how it looks? If I find a size that is more suitable to fit me (I’m a bit chunkier than the average prom attendee), I try it on. No harm, no foul. I probably have ten dresses now that I found on the racks in the juniors department.
My latest go to store is American Eagle, another store that caters to shoppers two generations younger than me. Ironically, it was my wife who was the reason. We were in New York last summer (I was in boy mode, as I always am with my wife, as I do not dress in front of her) and she went into an American Eagle store. While she is looking, I will look also. I really don’t care if someone sees a guy looking at women’s clothes, because that someone doesn’t know me.
I saw a red spaghetti strap top that I thought looked cute and it was on sale for (I think) $9.99. I took a picture and texted it to Ms. Dee-ism, another GG friend who I share lots of pictures with. She liked it too. As I was with my wife, I wasn’t going to buy it in front of her, but the seed had been planted.
We were leaving New York the next day, but before I left I went to a different AE store, seeing if I could find and buy the top. It was a different store, so they didn’t have it. Shucks.
But soon after I had a lunch with former co-workers at a food court in a mall, and this mall had an American Eagle store. Like a moth to a flame, I went seeking the top. Eureka! The store had it, and it was still on sale. The store also had a discount rack, and I saw a cute black skirt, size XL, on the discount rack. In for a nickel, in for a dime, so I bought both. The price for both was under $30, as I remember.
The skirt turned out to be a size too large, but I decided to be bold and return it to a closer AE store to see if they had a L instead (as a guy, again). They did, and so I now had a new outfit, one I wore for the first time at Dee-Va Las Vegas.
While buying the items, I signed up for membership in AE’s frequent buyer plan, or whatever they call them. As such, I started getting frequent emails from them. The looks and prices made for tempting combos; I bought a light blue summer dress, which also made it to Las Vegas, and a darker blue dress. Both purchases were online, and I had them shipped to the local store for free shipping. Yes, I walk into the store as a guy and pick up my purchases, which are generally dresses.
Now, when out dressed, I’ll go browse the AE stores at the mall (or the standalone stores in NYC). Yes, I’m older than most of the other customers, but again I don’t care. My last purchases were a blue top paired with some jean shorts, a top and shorts combo, and a blue floral dress (haven’t had a chance to wear that one out yet).
And that’s not to mention Akira or Dangerfield, which are both young and funky (or Plato’s Closet, which also caters to the young).
If it’s fun and cute and it fits, I’m game.
8 Responses
Dee,
I might be 75 but I choose not to dress as an average 75 year old would BUT I do have my guidelines , there’s nothing wrong with dressing younger but I have to consider the people I’m mixing with . For my painting groups I wear something comfortable and appropriate for the weather conditions , my skirt hems usually sit on my knee when standing but sometimes when engrossed in my painting they show more leg than normal . It must be quite an interesting view the other side of my easel , you can only see my legs , lucky them !! Afterwards I normally go for lunch with two or three other ladies so I like to look OK . For evenings out I consider outfits either ” TOO MUCH ” or ” NOT ENOUGH ” . Not enough can be blinged up with the right accessories , too much means you’re going to stand out for the wrong reasons , I know when I’ve reached that point because women give you the ” Looks to kill ” glances . I remember going to an incredible show performed by the Irish Guards Band , I didn’t feel overdressed with my outfit and knee length brown leather boots but two women sitting opposite wouldn’t stop scanning me from tip to toe and neither did one of the husbands !
I don’t really have a favourite shop , some of most gorgeous outfits have been picked up in charity shops , I picked up a lovely sequined jacket to go with an evening dress for my cruise , the comments I received were amazing . Again I got the looks from the wives when entering the cocktail bar before the evening meal , don’t worry girls your husbands are safe , I’m not interested , but it was fun !!!
Dee,
I like Express. I have my sherpas, many pants and many bodysuits and a few dresses from them. I like short shorts and wear in male mode. Many are from Eddie Bauer…now size 8.
My shoes are from everywhere, currently I’m getting more Jessica Simpson heels because they are taller than what other manufacturers are producing.
I’ve never really been in an Express. I’ve never really seen anything that enticed me inside.
I really haven’t bought many heels lately. I have a wide enough variety to cover most looks and I do have limited storage (and limited patience from my spouse) so these days I just haven’t run across a gotta have.
I’m with you 100%. Why women start to dress as in dullsville after a certain age escapes me.
Have purchased a number of maxi’s at Ross Dress for Less and they are very close to gowns while only costing $25. I’m older than you gals but figure I’m making up for lost time. The only concession I make is to wear these dresses at a fancy upscale place
You’re not the only one who loves to dress up. I’ve found when I go out I’m almost always the best dressed lady around. I hate too dress down but its the only way sometimes. Love your articles and go Macy’s!
Thanks!
Dressing isn’t a competition, because far too often I’d lose, especially with one of my GG companions! She gets noticed, so I get noticed–and she is freakin’ gorgeous!
Macy’s is good for gowns and juniors stuff. I try on the gowns and buy the juniors stuff, if on sale. It used to have a lot more changing rooms (post Covid a lot of their rooms are closed) and not a lot of staff, and the clearance racks are a good shopping opportunity.
That one awesome friend you have. Refered you to.the resale place that has a room just for gowns. Don’t forget him 🙂
That place has moved and I have not been to the new location, but when I get a chance, I will.
Mucho gracias, senor!