Lounge wear?

• Button-down: Covington via Craigslist
• Vest: Maurices (previously)
• Skirt: Sag Harbor via Craigslist
• Pumps: Naturalizer via Craigslist
• Pantyhose: Just My Size via Walmart

This was Wednesday's outfit, and it was almost completely created from recent Craigslist purchases. It's definitely a little different from my normal style, but the long wool skirt was really calling to me. Of course, that's probably because after warming up just enough to a relatively balmy 40's and 50's, it was back below freezing again.

I also wanted to take a minute to mention that I love answering reader questions, and a few posts ago, Cara from the wonderful Cara's Closet asked a question: An odd question, and possibly a question you don't want to answer (in which case, ignore me!!), but does your love of women's fashion stretch over into lounge/sleep wear?

First, within reasonable bounds, I will try to answer any question I can, and I certainly don't mind discussing lounge/sleep wear. I actually have been interested in extending my interest in fashion to lounge and sleep wear, but right now, I don't actually have anything like that. My current sleep wear is a pair of a cotton shorts and a cotton t-shirt, both from the men's section. It's actually fine by me, but they are getting a little worn out, and I have been shopping for some more "feminine" replacements. I haven't met with much success though, as most of what I've found either hasn't really inspired me, or has been too impractical, or just looks to... um... "granny-ish" for my preferences. The story is similar with lounge wear: I've looked off and on, but I haven't really found anything that has inspired me.

I think part of this is also because when I do go shopping, its easier to get excited about things I can put into my daily rotation, or a new pair of shoes. I have a similar problem getting excited about basics and layering pieces, and I have a similar gap in my wardrobe for those pieces. There are also many days where I don't get to dress how I want through the day, and I frequently try to dress up in the evenings, so, somewhat ironically, many of the outfits I post on this blog might be classified as "lounge wear".

Again, I love answering questions, so please feel free to email me, or leave them in a comment, and I will try to do my best to answer them in a future post! I tag all my answers if you would like to read past questions. And of course, the pictures in today's post were taken by my fabulous wife.

Short skirt and a long jacket.

• Button down: Old Navy
• Vest: Maurices (previously)
• Skirt: Old Navy
• Pantyhose: Just My Size
• Pumps: Nine West (buy (Cognac color))
• Jacket: Kohl's

This is another outfit from last week. When I put on this skirt, I realized it was a little shorter than I remembered when I bought it. But I figured it was okay, especially since I was staying indoors. And this is the blog debut for this pair of heels. I mention them because they are one of my favorite pairs of shoes. They're really comfortable for the height, and I love the color. I decided that if I'm going to be crazy enough to wear a short skirt in December I might as well pair it with a great pair of shoes. And I'll be honest... I just put the jacket on so I could use this title.

I know a lot of bloggers talk about how awesome the style blogging community is, but it really is. Its definitely made this holiday season more fun for me in a lot of ways both big and small! And there are amazing style bloggers like Bombshell Beauty who do wonderful things like this. And there are so many other wonderful bloggers out there too(like Megan, Pamela, and Melissa just to name a few. and I really can't link to everyone, the list is too long!) Anyway, thanks everyone! And of course, my fabulous and awesome wife took the pictures!

Long skirt and no jacket.

• Top: JC Penney (previously)
• Belt: Torrid (previously)
• Skirt: Cato
• Boots: Torrid
• Bracelets: Torrid (previously)

This is my only long skirt, and I bought it a while back because I wanted to try a longer skirt, but I'm never sure how to style it. The fabric is pretty heavy and its really warm, which is great when its below freezing outside, but that also makes it a fall/winter piece only. Unfortunately, this will be the one and only appearance of these boots on this blog. I've given them several chances to get broken in, but every time I wear them they squeeze too tight in the middle of my foot, which I think is a pretty weird way to not fit. They left my feet hurting after wearing them a relatively short time. I have 5" heels that hurt less than these boots. But enough with the negatives. I like how this outfit turned out, and I think the skirt worked really well, and I have plenty of other shoes that will work just as well with this.

I'm still behind on all kinds of things, but maybe I can get caught up on my blogs this weekend! This weekend we also have our first (and so far only) holiday party to go to. I won't be wearing anything I would post here, but that's okay, it should still be a lot of fun! And I really hope everyone has a great weekend!

Just as a reminder, I always enjoy answering question, so definitely feel free to ask away. And of course, as usual my magnificent wife took the pictures today.

Orange and purple.

• Top: Cato
• Cami: Cato
• Vest: Maurices (buy it)
• Skirt: Isaac Mizrahi for Target
• Purple Tights: JC Penney (previously)
• Boots: Target
• Bracelet: Torrid (previously)

I frequently associate orange and purple with Halloween, but when I put this outfit together, I was thinking they really work great for fall in general. I was also trying to break my neutral heavy rut. Of course, its cold like winter here, so maybe its not really time for a "fall" outfit anymore, and this was all just wishful thinking on my part. I know the short sleeves were wishful thinking, but I was indoors the whole time I wore this outfit, with no intent to go outside.

I have another question to answer today. This one is from the fabulous Pamela of Call Me Ishmael: Where do you most want to go dressed as a woman? For what occasion? I think you mentioned something about a wedding or ball before. Anything else?

What I really want is to get dressed in the morning without having to consider the gender of my clothes, and just go about my day normally. As it stands, I'm pretty sure that's not realistic most days, but I do feel like I'm close to a place where I can go out and about some of the time. It just takes some advance planning and preparation. However, there are some situations where I frequently find myself wishing I could wear an outfit I would post here. And since that's what Pamela asked, here is a list of those places in no particular order.

• I mentioned this one previously. I would like to wear a nice formal dress to a formal event. Maybe its because I remember all the formals, proms, and dances I went to while I was in school where I was often jealous of all the pretty dresses. One day, I would really like to get dressed to the nines in formal wear and go to really swank event or dance.
• This one is related to the previous one, but since I joked about it in the other post, I thought I would expand on it. I have always enjoyed weddings, and while I had a close male friend ask me to be a groomsman once, I have sometimes thought it would be really special if one of my close female friends ever asked me to be a bridesmaid. (And then my next thought is usually to ask myself what would a male bridesmaid be called?). Of course, this would probably be a horrible idea, and weddings should be all about the couple, but I like the idea of being there for my friends on their special day. Also, I have a long and highly qualified resume documenting my skills at extreme car decoration during the reception. Okay, maybe that last one isn't helping my argument! :) (Hehe, it also doesn't help that the idea of male bridesmaids shows up in pop culture occasionally, like here and here!)
• I also like the idea of going dressed up to informal parties and other social events with friends. This is actually something that I am getting the opportunity to do now, since I have a circle of friends who are accepting of how I like to dress. Its not like there are opportunities on an extremely regular basis, and most of our friends live one city over from us, but next year is looking up on this count.
• I'm sure to no one's great surprise, shopping is high on the list too. Especially the idea of making a real day of it with some friends, and going to a city with lots of great shopping options (and preferably reasonably far away from home for anonymity reasons...). Of course, this one is as much limited by budget as other concerns, so I guess I need to start saving up for it. :)
• A "(Mostly) Girls Night Out". The idea of getting dressed up and going out with small group of close friends to a nice restaurant, followed by a movie, play, or some other fun and/or cultural event or even a nice club. I'm not sure if this counts as irony, but I wouldn't actually want to exclude any gender from this sort of event. Earlier this year, some friends had a tea party and hosted a Mary Kay consultant during the tea. Afterward we all went to a restaurant and then to play pool. The evening was actually completely mixed gender. Okay, well, I was the only guy who elected to go to the Mary Kay part (the other guys watched a movie in a different part of the house), and I ended up changing before we went out for the rest of the evening. So I'm including this one because doing more things like this appeals to me, especially the part where I don't change clothes halfway through.
• I really enjoy office styles a lot, and so the opportunity to conduct business dressed up really appeals to me as well.
• When I was in college, a friend of mine showed up to class one day in a 3 piece suit. We asked him what the occasion was, to which he deftly responded, "Laundry Day." And so the last "place" it something I have probably mentioned before as well. Some days, I just want to get up and dress up for what many would say is "no reason at all". I do think there is a reason though. I want to dress up for myself, and when someone asks why, I don't want to feel embarrassed that I just wanted to look fabulous, and hide behind being out of "regular" clothes. (In all fairness to my friend, he was, in fact, completely out of other clean clothes. I guess doing your own laundry is a life skill too frequently learned in college.)

And of course more questions are always welcome, so definitely feel free to post more. I will always try my best to answer them. This week has been mildly crazy as well, so I must apologize for the lack of posts and being behind in general. And of course today's pictures were taken by my lovely wife.

Hair and makeup.

• Top: Maurices
• City Shorts: Maurices
• Boots: Payless (previously)
• Pantyhose: Just My Size via Walmart
• Necklace: Maurices (previously)
• Bracelet: Torrid (previously)

I felt really great in this outfit, but there are some things I'm not sure about. This button down is a little on the bulky side bordering on too big, but it can be cinched with the ribbon in the middle. I have seriously thought about removing that ribbon because I'm just not sure about it (As you can see, my bow tying skills are also a bit off as well...). If removed the ribbon would also be a pain to thread back through the fabric "loop" that contains it. I always enjoy everyone's feedback on my outfits, so definitely tell me what you think about this one!

In the previous post, Pamela from the awesome blog Call Me Ishmael asked a question: how long does it take wifey to do your hair and make up every time you take pictures and post? The answer is that it really depends. I normally wear my hair in a ponytail, and if I'm changing in the afternoon or evening and just going to wear one outfit and stay in, I'll just brush out my hair, but I do play around sometimes and try to fix my hair myself. I really want to be able to do these things for myself. (I also definitely intend to corner my stylist next time I get my hair cut and beg for lessons!) Likewise with the makeup. I want to learn how to do it myself. But most of the time for pictures I just brush out my hair and don't wear makeup (including the pictures in this post).

If we're going to go out though, I usually ask my wife to do my hair and makeup since she does a much better job than I do. I hope to get to the point where I feel comfortable doing it myself when I go out, but on the other hand, my wife does enjoy playing with makeup, so its not too much of a struggle to get her to help out there.

For makeup it normally takes about 15 minutes total. I start by shaving, and that takes maybe 5 minutes and then I take a break to let my face air dry. I should add that recently I have also experimented with using an epilator on my beard as well, but I still have to shave to get the hairs it misses. Fortunately, this experiment with hair removal went better than my last big adventure, I won't say its the most pleasant thing I've done though, but strangely enough it seems to irritate my face less than shaving (especially past the initial usage). I think I must have fairly sensitive skin. Anyway, with that done, we apply concealer for red spots/beard coverage, then use a loose powder foundation, blush, eye liner, eye shadow, mascara, and lip gloss. I could probably get away with less work on facial hair removal if I would use a heavier coverage foundation, but I don't really like any of the ones we've tried, and its been really difficult to match my skin tone on the heavier coverage too.

Hair takes a lot longer. Usually about an hour I think. I have fine, thick, straight hair, so it tends to take some work to get it to hold a curl. The last time my wife curled it in layers and used a spray gel before curling, and then hairsprayed it all when she was done. Its been tricky for my wife to figure out how to style my hair since her hair has a lot more natural curl.

And while this is not exactly what was asked, I do think I should add that the real time sink in getting ready is hair removal. Shaving my legs, chest, face, and armpits, plus using the epilator and tweezing just takes a while. I probably spend 4-6 hours a week on hair removal. So to go out for the evening like this post, I probably spend about 2 hours before getting ready, with my wife helping for about half of that time.

And of course my beautiful wife took the pictures for this post.

I'm not a lumberjack.

• Top: Maurices
• Denim Skirt: Maurices
• Socks: Target (previously)
• Boots: Payless

This outfit turned out far better than I imagined and it was extremely comfortable too! I really like plaids, but I have trouble finding plaid tops that work out, and that don't make me feel like I look like a lumberjack, but this one worked out pretty great I think (Not that its bad to look like a lumberjack, its just not the look I'm going for! ;) ). I was also a little nervous about the pattern mixing with the socks and the top, but I thought it worked out pretty great too. These boots are also a little different since they have zippers on the outside instead of the inside. Every time I pull them out of the box, I still find myself surprised by this and only remember because I'm trying to put them on backwards.

Oh, I'm still catching up on blogs, I haven't reached the "mark all as read" futility stage yet! :) And of course, my hair was done and today's pictures were taken by my beautiful wife.

My extra late halloween post.

My Halloween Costume

• Top: Maurices
• Skirt: Torrid
• Petticoat: Torrid (here)
• "Knee" High socks: We Love Colors (here)
• Shoes: Payless (here)
• Other shoes: Gabriella Rocha via Zappos(here)

My Wife's Halloween Costume

• Top: JC Penney
• Skirt: Hot Topic
• Tights: JC Penney
• Shoes: Payless (here)

We decided that our costume this year would be "twin" school girls. Since the party was going to involve a lot of dancing, my wife and I chose to wear identical flats. On Saturday, my wife was going to wear a different costume (I guess that one will just roll over to next year), and I was going to wear a nice pair of Mary Jane style heels with this costume. I'm glad I took both pairs of shoes for the pictures, because I really like the heels and I've been saving them back from the blog for this costume.

Earlier this year, my wife and I found a really cool hair salon from a friend's recommendation, unfortunately after our one and only visit, we found when booking another appointment that our totally awesome hair stylist no longer worked there. Instead of asking for a different stylist, we just did what most people do when presented with a frustrating low priority task: procrastinate until its a high priority. We ended up not booking another appointment until last week. We had both arrived at the point of really needing a haircut and I had a brilliant idea.

Brilliant ideas are a scary thing right? Thankfully this brilliant idea didn't involve Nair, and turned out much better. We booked our hair appointment the day of the party we attended. When booking the appointment, I asked if it was okay for us to come in costume. They said yes. Emboldened, I sheepishly asked if it was okay for me to come in crossdressed in costume. Silence. Oops was the thought that flashed in my mind. Followed by getting put on hold. Apparently, that request prompted her to ask her superviser. But she said that was also okay.

Fast forward to the day of the party. We arrived at the hair salon, and the stylists later said they were impressed with my confidence. I didn't point out that sudden moves, loud noises, or even a stiff breeze would have revealed how thin my confidence truly was. I was aware that some of the customers in the salon were staring a hole in me. Thankfully it was a fairly light crowd that afternoon. We lucked out with our new stylists. They were awesome, and just like the first visit, the real shocker turned out to be that I'm straight. The stylist had neighbors and friends that are drag queens, so crossdressing was no big deal to her. We mostly ended up talking about clothes and shopping. The stylists did an awesome job with our hair, and we were both extremely pleased.

After the hair appointment, we had some time before the party for pictures in an obscure nearby park. Since this really is a special post, and because I was exceptionally happy with my makeup and hair, I cropped the pictures a little higher (um, we also forgot to get a few planned shots in all the excitement, and yes, my amazing wife took all the pictures, except the ones of her, I took those). Since I've discussed hair removal before, some notes on these pictures: I just shaved really good with a new blade, and then we used concealer, and covered it with a powder foundation. This actually worked great, but the concealer showed through in some pictures later in the night when we used the flash. The problem is partially that I don't like full coverage foundation, and we've had trouble matching my skin tone as well. It kinda gets expensive to keep trying different foundations too.

We ended up getting there a bit early, and the first batch of attendees were mostly not in costume. That did change as the night went on, but it was still surprisingly light on people in costume. We didn't know anyone at the party. Honestly, it was probably easier that way. However, I was not the only guy in a skirt. There was a guy who seemed to fit the comedian category, and there were a couple of guys in kilts (Seems like I missed a category in my previous post).

While we were sitting out a song and watching other people dance, I was approached by a guy who asked me to dance. At first I thought it was just someone being silly and I said, "Noooo". Feeling a little awkward, my wife did jump up and agree to dance with him. He seemed a little off put, so my wife later reported the conversation something like this:
Wife: "Oh, don't worry, you just surprised him."
Guy: "Him?"
Wife: "Yeah."
Guy: "Uh... that's a pretty good costume" trailing into nervous laughter.

One woman forgot that it was costume night and asked if we were dressed for a sorority function. Another guy was teaching some dance lessons and asked if we "ladies" wanted to join the lesson. We declined. One woman told me, "You make a convincing girl". It was becoming clear that while not everyone was fooled, that some people really did think I was a female.

The main event turned out to be the costume contest judging. They asked the girls to line up so they could "strut their stuff". Quite reasonably, I thought, not every girl wanted to "strut their stuff" and so there were some holdouts hiding in the audience. The girls in line started cajoling their peers to get in line too, most of them eventually acquiesced. Finally, they started calling out to me.

At first, I thought it was a joke, I really did. But it was apparent that at least some of them were serious. I finally told them that I was a guy in front of everyone, and after a bit of pause one of them pointed out that I was in a "very confusing state". After that, I decided a low profile was best and didn't join in the men's line. Honestly though, I was also hoping that if we were going to be judged that it would be for a "ensemble" costume since my wife and I went together. I also found it interesting that several of the guys who got in line were not in costumes, unlike the women's line. The comedian crossdresser ended up placing second, and in strutting his stuff, did some comedic overplaying of femininity, and that's not something I was interested in doing, so ultimately, I'm glad I didn't participate in the contest.

I certainly take it as a compliment that some people thought I was a female, and I even admit that I enjoyed it. I want to point out though, that even if I were go out on a "regular" night dressed to the nines, being counted as a girl is not my goal. In conversations with my wife, I mentioned that I felt that I was getting stared at a lot. My wife pointed out that it felt more like being out with one of her female friends from college, in particular, the way males were looking us over. On a lighter note, I have never danced in a skirt, that part was also lot of fun. The spinning was one of my favorite parts! A lot of the people who did figure it out were extremely cool about it. The night ended up being a lot of fun, and this year ended up being a lot different than last year.

BBCA 5: Neutrals and Pink.

• Tank: Maurices
• Shrug: Maurices
• Skirt: Maurices
• Belt: Torrid (previously)
• Socks: Target (previously)
• Pumps: Payless

This outfit is part of Melissa's Blogging for Breast Cancer aWEARness challenge. I am seriously running behind on everything today, admittedly, a power outage this morning didn't help. And while I would have loved to write something more interesting, instead I'm writing that I wanted to write something more interesting just so I can get this posted. I did decide that I enjoyed the socks with heels look after trying it once before, so I thought I would try it again for this outfit. I definitely need to get some more socks, but the few times I've been out shopping lately I didn't see anything inspiring. Tomorrow will hopefully be a lot better! And of course, today's pictures were taken by wonderful wife!

September's Last Call.

• Top: Maurices
• Skirt: Maurices
• Belt: Torrid
• Wedges: Payless

This is an outfit from earlier in the week, and with the weather finally turning, I expect (er, hope?) this will be one of the last summery outfits I post until next year! And hey, its also the last day of September, which is a good thing, I think. September was a wild and crazy month for me and its ending with a wild and crazy day. My wife and I puzzled over this outfit too, she made some suggestions and I kept tweaking things until I just kinda stopped here. I really like it though, I think, but it still feels like something is missing. And of course my beautiful wife took the pictures and made suggestions about the outfit.