"Where am I going to wear this?"

[Jenniferathome]

This is the question my wife told me to ask myself when I first started buying things after coming out to her about 5 years ago. Of course, as a newly released-from-the-closet cross dresser I bought too much, too often and discarded so much (always to 2nd hand stores). I think this is a really common phase for cross dressers. As is hoarding of clothes. Somehow clothes become trophies.

I haven't been in that mode for some time but as I was culling out my closet, something I do three times a year, I started to think about what my wife told me to ask myself years ago. "Where will I wear this?" it's a great equalizer. All of the things I removed I had worn planty of times. I don't think more is the answer, but better is. One thing you can wear many times. So now, when I feel like a change up, I head to Rent the Runway, otherwise, I ask myself the question.

So, do you ask the question or is it more of a, "screw it, I want new stuff in my closet"? And if the latter, do you ever ask yourself, "why did I buy that?"

[Heidi Stevens]

You're describing my attitude towards clothes buying, Jen! I will always skip the low end stuff and wait for big sales on the better made and designed stuff. I also have a favorite consignment shop I go to when I want to find a well cared for upscale item or two. I just did a closet inventory and kept nearly all of it as they are well made basic items I will wear several times.

[StefaniLara]

Honestly, I'm still in the I-need-to-buy-more-clothes phase since I'm just re-entering the CD world after denying that facet of my for years. And yes, I do ask myself why I bought something.

[KrissyP]

That is a great question Jennifer, and I always include that thought process in my purchase. The other question I ask is what outfit will this go with or how can I match it with other things I already own? I don't have the room yet to have too many 1-off items. I like to mix and match and coordinate whenever possible.

[bridget thronton]

I think the process of planning what will go with a proposed purchase is a good way to keep buying in check (some what)

[grace7777]

I have many things in my closet that I have not worn in a long time. This is because when I first started dressing en femme, I was buying stuff all the time. Back then there was just an excitement in buy femme clothing. I was in what we would say is the pink fog.

Since then I have started to develop a style. It used to be I did not have a style so I bought many different things. So now, I ask myself where will I wear it, does it fit my style. It used to be I would buy clothes just for the purpose of buying them. Basically my approach now to buying femme clothes is the same approach I had to buying male clothes. So this has resulted in me cutting back in buying femme clothes.

Also I now view myself as being trans, and not as a crossdresser. So now it is not just about the clothes any more. This has also cut down on me buying femme clothes.

[Erica Marie]

Hi Jenn, I have been through the "more is better" phase. Now I am like you, If I can't put it my closet and wear it on a daily basis I dont waste the money. I would rather buy a couple of nice, more expensive things than just a bunch of stuff just to know I have it.

[Claire Cook]

Hi Jenn,

Yes, been there, done that! You've made a great point -- I wonder if all of us when starting out just bought anything as long as it was female, then as we "grow up" start looking more carefully at what we have and what we wear. We've already gone through Round One of GoodWill donations, and I still have stuff I've never worn out of the closet. Part of it may be figuring out just what our personal styles are.

But then again, what girl doesn't go through phases like this??

[audreyinalbany]

I still sometime go out and buy something new just for the hell of it. I could ask myself the "where will you ever wear this?" question a thousand times and get the same answer..probably right here in my house considering the rare times I go out dressed. Still it's fun to have a few 'dressy-dresses' just to get dolled up once in a while.

[Sara Jessica]

I sometimes make the mistake of equating a worthwhile purchase on how much I wear it out & about, giving no value towards how much I might wear something within the confines of my own home. The problem with this is that 2015 wasn't a particular great year for getting out & about.

As such, I ended 2015 with a "resolution" NOT to buy anything during 2016. My closet needs nothing. Although managed to break this almost immediately, I am going to do my best to stay the course. Hopefully the angel on my shoulder will ask "do you really need this?" which is kind of the same thing as "where am I going to wear this?"

So where am I going to wear _____? Hopefully out & about this year more than the last. Everything I own is fair game. The only thing I lack is enough days to give all of the outfit combinations a day in the sun.


You're describing my attitude towards clothes buying, Jen! I will always skip the low end stuff and wait for big sales on the better made and designed stuff.

I have to give you a shout-out Heidi as this is exactly my POV as well.

[Jenniferathome]

Sara, my wife told me that I actually HAVE TO buy things throughout the year for seasonal and trend changes. Funny she'd say that to a cross dresser! But I think she's right. One great piece that can bring 4 others to life, so to say. But, like you, I don't get out enough to wear out my clothes so buying has to be strategic for me. If I come across that perfect, timeless LBD, I'd buy it. For the really dressy stuff or trying a really different dress, it's RTR!

[shawnsheila]

Oh yes... I bought everything and everything when I first started dressing.. both for the thrill of being out shopping and the and the misguided belief that I would look like the models (or at least more femme) in the clothes they were wearing. Now I look at shoes/clothes and see how practical things would look on my body shape and to make sure its something comfortable and I like it. I still pick out special occasion items to wear but its no longer the nervous rush to get something before someone sees me. I like to take my time and think about a purchase.

I also agree about waiting for nice items to go on sale instead of picking up the cheapie things now too :)

[Stephanie47]

This morning I just finished updating my word document of dresses i own. It's now 131. I have a picture from my eBay and on-line purchases in a folder. Each is numbered and entered on a word document as to label, description and size. I know I will never hang them in a closet. I know it is impossible to wear 131 dresses in a reasonable period of time. My wife knows I am a cross dresser. We share the same size with some labels. I'm sure she'd just fall over. Forget that I have over 400 full slips.

The answer to your question is "retail therapy." I also buy military plastic models that I intend to build before I pass on from this world. Will I get to them? Probably not, but, there more of a chance I'll build the 75-100 models than wear 131 dresses...and counting. Forget the slips. I do go to see a counselor and belong to a support group for issues unrelated to cross dressing. I've discussed with the counselor that I seem to buy models when under stress. She calls it "retail therapy." It's can be an outlet to indulge myself when I need to the comfort of something I enjoy. I enjoy appearing as a woman because it helps avoid certain aspects of prior life events that were not enjoyable. My counseling is free, but, I think it would be less costly to buy dresses than pay a counselor and still buy dresses.

Yep, I bought another six dresses over the Christmas break.

[AngelaYVR]

A while ago I had already decided that I had to love anything I bought. Not just ok - it had to be near-perfect. This worked well and I'm at the point where I'm not buying anything anymore although I reserve the right to purchase something if it happens to be absolutely amazing. The trouble with women's clothes is that there is always something nice to be had so you just have to stand firm.

[Sarah Doepner]

I've gone thru various stages or phases where my shopping has reflected my mindset at the time rather than what would be good in my closet. So yes, I did have a lot of very "girly" things in there that didn't reflect my size, age or willingness to step outside the house. For the last couple of years now I've been trying to use exactly that question, "Where will I wear that?" before I buy something. The thing is when it's a semi-casual top, it can be worn anywhere these days, so now I've got more than I should have. The magic thing was when I hit "critical mass" in tops, skirts and pants and everything I bought managed to create several new options (that I'll never get a chance to wear) and part of the reward in shopping was to see what it did to my closet. I've been attempting to cut back and have even cleaned a lot of things out of the closet over the last few months. I've taken a lot to the local thrift shops and it's time to do it again.

I have been knocking down some barriers recently and feel less constrained than I have before, willing to get out and do things en femme. Unfortunately that corresponded with me breaking my foot and limiting my ability to get out. Spring will be a new season for Sarah and it will be a good time to evaluate what's in the closet that can be an answer for "Where will you wear that?"

[Diversity]

I often buy things for the thrill of shopping, especially when I have not been able to dress for a long time.
Also many times I just want to try something on when I get home just to see how it looks and feels.
Your post is timely, as I am about to do a purge in the next few weeks.
Have fun!
Di

[BillieAnneJean]

In the beginning I didn't have much, so if it fit and I kinda liked it I bought it. As long as it wasn't expensive. Way more resale than new but still a lot of new. And a LOT of resale. I accumulated a great selection. It took three years.

Now I am at a point where I am saying I won't buy anything more unless it is exceptional, that I have enough now. But I still go to Goodwill (GWs) and I still find really great stuff. Like a silver skirt suit that I bought last night for $5.99. It needs buttons as 1 of 3 is missing. Otherwise it is fabulous and very different from anything I have. A silver summer weight somewhat dressy skirt suit. Fits perfectly except I will have to shorten the skirt as it is about four inches below my knees. It will take me a couple of hours to shorten the outer layer and the liner. It really is two skirts to shorten. The buttons will take fifteen minutes.

I LOVE the clothes and the incredible variety. Most of my stuff came from GWs. $5.99 for dresses, $7.99 for skirt suits, $2.99 -3.99 for skirts, occasionally more. The new and designer stuff I bought from GWs can be double the price. But most of my GW stuff falls in the lower end. Yes I have about 5% of my stash that I bought new from Macys, Kohls, Burlington, and the like. I am MUCH happier with the GWs stuff because of the uniqueness and low cost. Unusual without the guilt. I really talk to myself before I buy anything new. The standards are WAY higher.

Now I look at each item, resale and even more so new, and say to myself, do I need it, will I wear it, do I have other items that work with it, like shoes, purse, bling. So the incoming has slowed down a lot.

I feel so very fortunate to have a great wardrobe selection.

But now I must raise the standards because I may soon get to a point where I have so much that it will take me years to wear it all.

SUCH FUN!
Billie

[kittie60]

Nope. I never ask myself that question cause I know someday I will need that special dress. Maybe not in the near future but I know I will, it might be a year down the road but I have it.

[Karen RHT]

Similar to Angela, (perhaps because of her :)) I've become much more selective about what I buy. Unlike Angela, I rarely get out, but that doesn't deter me from being selective as I build my wardrobe. For example, I had numerous opportunities to buy cute blouses over the holidays but didn't purchase anything. A week or so ago I picked up two blouses that I felt were perfect for two of my skirts.

To answer your question Jenn, I do ask myself the "where will I wear it" question. Difference is I have to qualify my answer with a "someday" attached. :daydreaming:


Karen

[GretchenJ]

Absolutely,

I have bought items that looked great on the hangar and then put it away. When I took it out and put it on, it was like I was in some kind of psychotic state, stuff that was totally not age appropriate, or I bought something to match something else I bought earlier, only to determine that it clashes badly (the pitfalls of being color blind)

Off topic - is that the new wig in your aviator picture, I hope it is because it looks soooo great on you. It frames your face perfectly and I love the color and the style. Kudos to you wife on her good taste!

[Sometimes Steffi]

I have to admit that when I first started buying girl clothes, it was retail therapy. Now I can be more selective because I don't need as much therapy.

[Jennifer0874]

When I first started buying clothes it was almost exclusively short skirts. Too short and a little trampy in the beginning. When my wife really started going out with me dressed she put a stop to that and really educated me on fashion. Now I love jeans and well put together modest clothing.

[MissTee]

I went thought the buy everything phase. Stopped when I had no more hangar space. Then I discovered under the bed, vacuum collapsible clothing bags. Created some closet room, then quickly filled it again. Don't do that anymore, and twice a year I selectively purge and the local women's shelter celebrates their secret Santa packages.

Thus, I now buy the occasional seasonal item(s) in great moderation. My weakness is still cute skirts and cute panties, so those I slightly buy too many.

To all that I do not go out dressed, but I do want to look good for my wife and the audience in my head.

[Robin414]

"Where am i going to wear this?"

My first time dressing in over 20 yrs I'm pretty sure I looked like Marilyn Monroe took up prostitution...wonder why a city park maintenance guy was stalking me in his truck? 😦 Speaking to the point though, I did binge a little when I found LTS but now I'm settling down I'm more selective and I'm beginning to really think about "Where am I going to wear this?"

[Sara Jessica]

UPDATE... To heck with my so-called resolution. Two weeks in, yesterday I couldn't resist these Michael Kors shoes (tasteful leopard is one of my "shiny" triggers). $27 at Macy's, regular $120. But "where am I going to wear this???"

[Amy Fakley]

Before I came out to my wife, I had a single Rubbermaid storage bin in the attic to hold all my girly stuff (figured the best place to hide a tree was in the forest, lol ... Indiana Jones style). Because of that, I had to be VERY choosy about what I bought and what I would keep because there wasn't really enough room but for maybe three outfits and a couple pairs of shoes.

After I came out, my sweet wife gave me a corner of the closet. Then she took me shopping. I'd been so terrified of in-person shopping before that, I'd had to do everything on the Internet. She held my hand and introduced me to the ladies department ... And most importantly the clearance racks. OMG, I was like a kid in a candy store! She'd created a shopping monster!

Though I rarely bought anything for more than $20, Over the course of a year or so, I managed to accumulate a completely ridiculous wardrobe. If it was pretty, and it was cheap, and it was in my size, I almost always bought it. I think partially, that was because it was so validating. It was like a breath of fresh air after so many years of staying on the "right" side of my self imposed fence around the ladies department. And just knowing that it was "ok" ... Especially shopping trips we took together, God that's fun ... And especially in the early days, it was pure euphoria.

Some pieces I will never part with, because even if I never wear them, they are trophies to me ... The first pair of shoes I ever had the nerve to try on in the store ... The first dress I ever bought myself. The first dress my wife ever bought for me ... My first wig (beat up and ratty though she is).

These days, I surely don't buy as much as I used to, and sometimes it's even practical. For the most part the "where will I wear it" question isn't that relevant because I get out twice, maybe three times a year at this point. So if I'm just playing dress up around the house and the princess dress is only $15, then WHY NOT?! :-)

[Jenniferathome]

UPDATE... To heck with my so-called resolution. Two weeks in, yesterday I couldn't resist these Michael Kors shoes (tasteful leopard is one of my "shiny" triggers). $27 at Macy's, regular $120. But "where am I going to wear this???"

At least it's a kitten heel. Makes for more options.

[SHY KIM]

That's a good piece of advice! That's why I love the forum. Since joining a month ago I have really come across some really good information (AND INTERESTING TOO I SHOULD ADD)
I have been on a bit of a shopping rampage over the last month or so since I'm just coming back out. It dawned on me that I better slow down and work with what I have in my closet for a while. With luck the items I have now will be to big by next fall:) Then I get to shop more!!!
Stay warm
Kim

[~Joanne~]

When I first started shopping I did a lot of that, bought all kinds of things that I thought was cute or wanted to try and then later on thought, why did I buy that? I won't lie, I still have a few things on my list that i want to buy that make no rhyme or reason and surely would never wear any where other then in the house but for the most part now, I buy things that are pretty, practical, and could be worn out if I decided to leave the house dressed.

[Vale]

Hi Jen, I also have a shopping filter, except as a mostly closet dweller my question is more like, "What fantasy will I wear this in?" Clearly this is a somewhat less restrictive filter -- and great fun.
Cheers,
Vale

[sometimes_miss]

Funny, I remember a female co-worker asking me the same type of question 35 years ago when I was looking through a GQ magazine (though, she was referring to my looking for more fashionable male attire, not female). She knew I wasn't going out to clubs, and my style was basically motorcycle guy. It was that comment that started me changing who I was, and what I did in my social life.

[Ceera]

So far I think I only have one dress that I purchased while knowing it was unlikely I would wear it outside of certain limited situations. My daughter and I are both Doctor Who fans, and we both attend anime cons and Sci Fi cons. I saw a darling Doctor Who themed dress at Hot Topic a while back. The fabric is printed with a dark blue space theme, like a starry sky, and on the skirt is Doctor Who's T.A.R.D.I.S. time machine / space ship. Probably the only place I will ever wear it is at an anime con or a Sci Fi con, or to go see a Doctor Who movie. I went so far as to ask to try one on while in male mode at a Hot Topic, and later ordered it in the correct size for me.

I ask the 'where will you wear this' question with all potential clothes or shoes purchases, for either gender. I usually shop for high quality clothes on good sales, and buy things I know I wil get a lot of use out of.