An outfit for driving.

• Hoodie: Maurices (buy)
• T-shirt: Old Navy
• Jeans: Maurices (previously)
• Boots: Clarks via Craigslist
• Socks: Hanes

Since the beginning of the year one of our ongoing projects has been to get rid of some excess stuff, either by taking it to consignment and thrift stores, or by selling it on Craigslist. This plan has a flaw I have recently discovered: other people on Craigslist have things I want, and so I end up "window shopping" the other listings. And that is the genesis of this outfit. I found a listing for a formal dress on the cheap, and while I have no "reason" to own one, I found myself realizing that it would be really nice to try one on, and own one "just in case", and the seller was offering an excellent deal, and really, this is all just rationalization for the fact that I want to make up for wearing a tux to my HS prom. So I sent an email, and scheduled a time and place to try on the dresses to make sure they fit. I realized that since I would mostly be driving and trying on dresses, I might as well dress how I wanted. And so after a pleasant and chilly afternoon drive, I am now the proud owner of a formal dress, and pleased with my outfit for the day. Even though this outfit spent more time in the vehicle than it did outside.

And of course today's pictures were taken by my wonderful wife. And I am slowly getting back into the swing of things with blogging and commenting, it only took the first two months of 2011 to do that. Thanks everyone for your comments and reading my blog!

Funky office casual.

• Blazer: Maurices (previously)
• Tube top: Maurices
• Cropped pants: Torrid
• Pumps: Payless

I've had this tube top in my closet for a while, but I've not been satisfied with my attempts to style it until now. And while a tube top is not something I think most people would count as acceptable office attire, I think it works well under this blazer. Admittedly, since I work from home, any discussions about acceptable office wear are purely theoretical. (And let's face it, in my case, most people are going to get stuck on that whole "crossdressing" thing instead of noticing the tube top...). And while I'm not sure if it shows up in the pictures, but the shading on the pumps are actually polka dots that slowly get bigger and more dense toward the toe.

I have one more outfit from my backlog to post, and we're still having to share computers in our household (not much longer I hope!), and of course in addition to being so gracious with her laptop my amazing wife took the pictures for today's post.

What we actually wore: Valentine's part 2.

My Outfit

• Button down: JC Penney (previously)
• Pants: JC Penney (previously)
• Tie: JC Penney
• Oxfords: ? (previously)
• Belt: JC Penney

My Wife's Outfit

• Dress: Maurices
• Belt: Maurices
• Pumps: Maurices

I'm a little later than I meant posting this. (Wow, take a day off and the rest of the week goes nuts.) But I wanted to post what we actually wore for the big date. And some of the pictures from the evening. The evening started when my wife got home from work about 10 minutes after my previous post.

I was afraid my wife might be forced to work late, so our reservations were late enough to provide some extra time which we didn't need. So instead, I took back roads that my wife is less familiar with, and slowly drove by a lot of restaurants which also would have been suitable for the day. (Okay, and I also drove past a few fast food restaurants too, just to add more suspense...). The good news is that when she finally saw the restaurant sign, she was too confused to guess if it was our destination or not.

Neither of us had been to a Brazilian steakhouse before. But I have to say if your budget can afford it, I highly recommend the experience at least once. Unless you're a vegetarian: while they did have a pretty cool salad bar, the meats are what makes it awesome, and its not exactly a vegetarian/vegan friendly sort of place. For those who don't know, the staff is constantly circulating through the restaurant with skewers of steaks, and they constantly stop at your table and cut off whatever you want in whatever quantity you want. And it's all you can eat. I had the funny idea I wanted to sample one of each thing on the menu, but I couldn't make it. We did save room for dessert though. I'm not sure how. So after the restaurant, I suggested coffee at a Starbucks near the hotel, which my wife agreed to, still in shock over the pleasant surprise of the restaurant. After coffee, I feigned getting lost only to pull into the hotel parking garage a few minutes later. My wife was speechless at this point. I later showed her the previous blog post and everyone's comments, which she thoroughly enjoyed reading. The only real downside is that I have no clue how to top this next year.

And of course, my very surprised wife took some of the pictures in today's post, and I took the rest for once. I hope everyone has a wonderful (and possibly long) weekend, and maybe someday I'll get caught up on everything I'm behind on (including your wonderful blogs...)

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.

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.

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.

A peek in the closet.

• Dress: Lane Bryant (here)
• Tights: Lane Bryant
• Pumps: Lane Bryant (here)
• Pearl Necklace: Torrid

Okay, this week has been incredibly busy, and that was before I got short notice that a friend who I haven't seen in years was going to be in town. But I've missed the style blogging world, and I'm incredibly behind on reading blogs (again), and I've really wanted to post more than twice this week, but we've barely had time for outfit pictures even. I will definitely be trying to take pictures earlier next week, and put some color back in my outfits as well (I can clearly see that I've gotten in a bit of rut lately...)! I'm so behind that I even have two questions to answer in this post. Luckily, they are related... er, well, I'm going to make them related enough to fit in the same post. And of course, questions are always welcome, and I will do my best to figure out some way to answer them (even if it takes a few days to write the post).

First, Lisa from the awesome blog respect the shoes asked here: This is the second pairing I've seen of someone wearing a filmy printed blouse under a LBD - I think it is a great combo and totally works. You look great! (I'm curious (and you don't have to answer if you don't want to) - how big is your closet? Do you keep two different wardrobes?)

The next question comes from Becca who posts at the really cool blog Free Honey, and she asked: Hi Matt! I don't have much expertise in the area of cross-dressing, but I always notice that they have tons of large sized shoes at Nordstrom Rack. I don't know if they have one in your area, but it would be a total treasure trove. I always wondered who was buying up the size 13 cherry red patent peep toe pumps!
Also, while you're taking questions - I have to ask you, do you cross dress all the time? Do you wear women's clothes at the office or in the store or do you generally just wear them around the house. I'm thinking that if you wore you're best clothes out to the stores, no one would think twice about you trying on ladies clothes. Hide in plain sight!

I do keep my "masculine" labeled clothes separate from my "feminine" labeled clothes. Some of this is because I happen to enjoy sorting things: in addition to being sorted by gender label, I try to also keep everything sorted by color, season, type of clothes, and any other category that strikes my mood at the moment. I would say that I have "1.5 wardrobes": I actually have a lot more "women's clothes" than "men's" (uh, I am a male, so I think it's also fair to claim they are all a man's clothes, because I own them...).

In terms of physical space, I have one closet in our apartment dedicated to "women's" clothing, and two racks for my shoes (one for shoes that no longer have a box, and a shelf for shoes that still have their box). I have a shelf of accessories, and a canvas tote of tights and pantyhose. I also have a small stand alone "wardrobe" for my articles of "men's" clothing, and a chest of drawers that contain fold up clothes and underwear of both "masculine" and "feminine" origin.

There are a lot of reasons for the lack of masculine clothes. I tend to have more fun shopping for "women's" clothes and shoes (uh... based on the numbers, too much fun shoe shopping, apparently...). I have also let my more masculine wardrobe atrophy for a lot of reasons (e.g. I work from home most days), and while I do have a plan to balance things out a little more evenly with future purchases (and to just generally have more fun and liberty with male fashions), it takes time to make major shifts in wardrobes. Another reason why things are a little out of balance, and this gets to Becca's question, is that I usually crossdress some every day. At this point, I only have one pair of men's jeans, for instance. I also have some women's shoes that are more ambiguous that I wear frequently, and I actually have a preference for panties (uh... so much for the boxers or briefs question... I hope this wasn't TMI...).

For the type of outfits I post here though, I generally only wear them around the house. I also work from home, and if I'm not meeting clients or running errands or have some other reason to leave the house, I do take advantage of this to dress through the "work day", but I suppose that's not exactly the same as wearing my clothes to the office. I am trying to find more opportunities to go out "socially dressed", and I have some friends that have no problems with my clothing preferences, and that does afford some opportunities to go out.

Since starting this blog I have felt more secure about going outside though. I spent many years dealing with extreme amounts of shame for my interest in feminine clothes and shoes, and I spent plenty of that time being furtive, stealing glances at clothes I wanted, and trying, in secret, to wear them. I'm not interested in that anymore: it's not pleasant, and it wore me down emotionally and didn't help me become a better person. I would also point out that it's not my goal to be perceived as a female. If someone did, I would certainly take it as a compliment, because I know how I'm dressing is "coded" female by most people, and see why someone would think that, but still, it's not why I want to dress this way.

Writing this blog has helped me see that plenty of people would be fairly cool with how I'm dressed. I'm also quite sure that some people would not be cool, but many of those people would also have enough manners to keep it to themselves in most situations. I suspect some people would probably be inclined to make comments, or laugh at me, and I won't lie, that's not something I want to experience, but at the end of the days it's not the worst thing that could happen. I do know that if I go out, some attention would be inevitable: I'm 6 feet tall in flats (and those would usually be size 12 flats...). While I know men and women come in all shapes and sizes (and I think that's a great thing actually!), and I even personally know women who are taller than me, bigger than me, with bigger feet than mine, I still think due to my height and size that I would get some unwanted attention and scrutiny. I also have a few concerns, whether they are rational or not. I worry about that "one" person: the person who will be bothered enough by what I'm doing to take matters into their own hands and go beyond verbal reproach. My other concern is related to where we live. We don't live in a huge city and that means I frequently run into people I actually know in public, and I have plenty of acquaintances and family I could encounter that I really just don't want to discuss this with.

When it comes to shopping, I do have another concern. To my knowledge, crossdressing is not illegal, but dressing rooms are a place where there is some expectation of privacy. My license says "male", and while a clerk, or most shoppers even, might "read" me as female, if one person didn't, and took offense, the perception that I was engaging in a "deception" might not end well. If I'm not trying to pass myself off as a female, then there is no deception, and that just feels more honest and safer to me. I guess I partially think of dressing rooms as a bit like public restrooms: Seriously crossdressed, I would be uncomfortable using the men's restroom, but it would likewise be inappropriate for me to use the women's restroom, and while unisex and "family" restrooms are more common these days, they aren't universal.

It would be nice to go out more often. But I do get opportunities occasionally. It's sometimes a frustration to me that I don't feel like I can just dress up and waltz out the door. If I want to go out dressed up, it ends up being the dominating factor in our plans, and I would rather it fade into the background a little more. And maybe it will as time goes on and we find opportunities and places where it's no big deal. Sharing with other style bloggers has been an amazing outlet for me though, and frankly, writing this blog is probably more fun than going out on a regular basis.

And of course, the outfit pictures today were taken by my amazing wife.

More on retail therapy.

• Top: Maurices
• Blazer: Maurices
• Skirt: Maurices
• Tights: Lane Bryant
• Pumps: Payless

I surprised myself by how much I really liked this outfit. I know this has turned out to be a neutral heavy week here, but its fun to mix things up, and I have been inspired by similar combos on several other bloggers lately. I have trouble styling this blazer though. I like the cut on it a lot, but unlike my other blazer it has a row of hook and eye closures instead of buttons to close it. I should have made a picture with it closed for this post. I know I could always just leave it "unbuttoned" like here, but I always enjoy hearing other people's ideas.

Pamela of the awesome blog Call Me Ishmael asked a question in a comment: #1: Ummm ... do you wear a padded bra? If not, what do you do? #2: Do you try out women's clothes when you go out shopping? Have you had to answer (or ignore, lol) questioning looks or straight up questions? First, I want to say that I love answering reader questions, and I will always try to do my best to answer them.

Part 1 - I have experimented a lot over the years, and my current approach is pretty close to what Pamela guessed. I usually buy padded push-up bras with molded cups. The cup size I buy is probably a bit generous, but thanks to a complete lack of visits to the gym and a diet that is at times questionable, I definitely have more curves in the chest than average. When wearing these bras, there is some extra empty space to fill, so I also use 2-3 "cleavage enhancer" pads I bought at Walmart to "stuff" the bra.

I have actually found that plenty of my tops enhance the appearance of my bust even without a bra, and I do have a "properly" sized bra with smaller soft cups that I sometimes wear that also helps with that "illusion" as well (I haven't worn that one in any outfits on this blog though). Its interesting: normally I am a bit self conscious about my chest when dressed in a masculine fashion, but in feminine clothes I hardly think about it. I have sometimes considered not wearing a bra, and for this blog I have an ongoing a debate in my head about whether or not to "enhance" my bust. Ultimately, I like the look though, and it does help my tops fit better. I have trouble fitting tops because I have a large-but-flat chest, and tops in my size tend to be cut for a more generous bust, so the stuffed bra helps account for that too.

I has occurred to me that the human chest, male and female, comes in all shapes and sizes, and that's pretty great actually. I don't think there is anything wrong with anyone, male or female, being flat chested, or having a large bust, or anything in between. Everything I have bought to enhance my appearance is an item marketed in common stores to help people change their appearance in a similar way. There is nothing inherently gendered or wrong with wanting to play with the curves and lines in a person's figure. And while I think some people would encourage doing this to hide physical features they don't like or enhancing physical features that they approve of, I don't think it has to be that way. I want people to be happy with their bodies, but I don't think being happy with your body has to exclude you from using clothes to change aspects of your appearance.

Part 2 - I have talked about some of this before in Retail therapy, and I even had some notes for a follow-up entry, so I get to answer Pamela's question and write that follow-up post! I always want to try on clothes before buying them, but its hit or miss on whether I will get to. It depends on how adventurous I'm feeling, how my wife is feeling, whether the dressing rooms are unattended, the specific store, and quite possibly the phase of the moon (okay, not really...). In stores like Target or Old Navy that stock men's clothes, most of the time I just try to discreetly fold up the clothes with something less obvious like a sweater or a button-down on the outside and use the men's dressing rooms, although I did have an awkward experience at Target recently. The dressing room was attended and the associate was a little shocked and said, "Oh, for a minute I thought those were women's clothes" but she let me go on in. In general though, I've found the store staff to usually be more understanding, and I even got to go back in the stock room at a Nine West once (it was mostly because the store only had 6 shoes in stock in my size, and it was just simpler for her to show me what they had rather than let me wander around the store asking her if they had a shoe in my size only to discover, repeatedly, that the answer was "no"). I asked that particular sales associate if this had happened before and her answer was "all the time".

At stores like Maurices or Torrid that stock only women's clothes, my wife has gotten reasonably good at trying things on and making a guess about whether or not it will fit. Recently, however, I noticed that some stores have allowed male companions to share the changing room: I presume its about minimizing dressing room traffic, but it might just be a sense of futility about keeping them out. Since then, we've asked a couple of times at stores if it was okay for me to go back, and the associate always said yes, and we were both escorted to the dressing room. The most common questions we get are from associates during checkout expressing surprise about the sizing. I suppose some associates get pretty good at sizing people visually and correctly guess that my wife is not that size, but they don't question it too much, and we've never told them the truth about who the garment was for. I've also had associates discuss how wonderful it is that I love to shop with my wife while I'm waiting outside the dressing rooms. Oh, if only they knew! :) For what its worth, I really appreciate my wife's help in this, and it makes shopping a lot easier for me.

I also need to say I do a lot of online shopping too. And its not entirely about trying stuff on. Sometimes its hard to find my size in stores. For instance, Payless almost never stocks my size, so I'll often visit the store just to see what a shoe looks like, and then go home and order it. Sometimes they have my size, but usually not. At this point, I'm pretty familiar with store return policies, and we do try to take advantage of stores that take returns from online sales and free shipping to store locations as well. Also, there are several brands and stores that I can trust to be pretty consistent with the sizing, and I can usually get away without trying their stuff on.

I usually feel extremely self conscious while shopping for myself in the women's department, and I tend to think everyone is staring at me. I really don't like lying, and if I were shopping on my own it would be really easy to say I was shopping for my wife, it definitely feels more unusual to say that about shoes and clothes rather than jewelry and other more traditional gifts. It is interesting though, sometimes I do shop for my wife and I have shopped for other women in my life before, and I definitely experience a lot less apprehension. In discussing this with a friend, she told me a story about shopping in the men's department for clothes for herself once. She actually mentioned experiencing feelings that sounded similar to my own, although her reasons were more about practicality and fit rather than style. My wife also has several items of menswear that she has bought for practical reasons and without a second thought. On the other hand, I know that plenty of women do shop for clothes for the men in their lives, and shop for themselves in the men's department as well, and it does seem more socially acceptable. I always find asymmetries like this to be really interesting to think about. I've said it before, but I'm personally a fan of moving past gender labels and clothing.

I love answering questions, but I have some questions for anyone reading this today who feels like answering. (If you don't want to, that's great too!) I'm curious if anyone has encountered crossdressers while shopping? Also, for anyone who has worked in retail, I'm curious if you've ever had a crossdresser ask about dressing rooms or if stores that only stock women's clothing have policies about crossdressers? Also, if you have shopped for men in your life and shopped for yourself in the men's department, do you experience any differences in how you feel while doing so?

Again, I always love answering questions, and questions are always welcome! I will try to do the best I can to answer any question if I can. Oh and of course today's pictures were taken by my fantastic wife.