Dressing Up and Dressing Down

Sometimes I wonder if it IS all about the clothes, the makeup, the heels.  But it’s not.  It’s about not feeling comfortable being tied to a specific gender for my entire life.  It’s about feeling comfortable as more than one gender presentation.  I feel just as confident in a suit as I do in a little black dress, but for different reasons.  I don’t want to transition because I like being able to choose my gender presentation whenever I feel like it.  As I get older, I also feel more hesitant to use phrases like “always” and “never” when it comes to my opinions about some things.

Of course, there are exceptions.  Like, should you wear open-toe heels with black stockings?  NEVER.

Oscar Wilde wrote “You can never be overdressed or over-educated.”  I agree.  I like to dress and look my best.  When I am out, I know that I am probably overdressed on some level to hit the mall.  But after days of shirts and ties, the sound of heels clicking on the floor in a department store is heaven.


When I was younger I used to dream about certain clothes.  I would page through the Victoria’s Secret catalog and wonder what it would be like to wear a matching bra and panty.  I would see girls wearing formal gowns and I would picture myself in such a beautiful dress.  In my closet I am lucky to have everything from leather to sparkley.

There are still outfits on my wish list but let’s be honest, after a certain number of bodycon and little black dresses, it becomes harder to find a dress that becomes a must-have.

Lately I seem to be drawn to a more casual look.  I have tried this in the past, such as pairing a cute top with a cardigan for example, but as I look through my wardrobe I don’t have a lot of outfits that are perfect for a lazy day of going out for coffee and running errands.


I don’t mind stopping by Starbucks or Target in four inch heels, but when I see girls wearing cute, comfy clothes I start to wonder if I could pull off the leggings/tank top/hoodie look.  I’ve been hesitant to try this in the past as I feel that layering gives me a “bulkier” look, especially my shoulders, than I would like.  I also think that if I am only going to dress up a couple times a month, do I really want to pass up a chance to wear that cute new dress?


Of course, expanding one’s style also feels expanding one’s wardrobe (which is exciting and also expensive).  I have an extensive collection of heels and a perfect dress to match each pair, but I have exactly zero pairs of shoes that would go with a more casual look.

I have a photo shoot next month and I am starting to pick my outfits for it.  I have a few new dresses that I am going to model for certain, but I might slip in something a little more causal as well.

Any suggestions for me?

What look do YOU want to try?

Love, Hannah




19 thoughts on “Dressing Up and Dressing Down

  1. Hi Hannah
    I love my casual clothes I have many pairs of jeans and tops some leggings which are a girls dream in casual, all you need are some flats to with them and your set I would love to see what you put together in your photo shoot.

    Liked by 1 person

    1. I do wear “girl” jeans in male mode (and today I paired it with a black t-shirt from the women’s department). I think I might put something together based on your suggestions! 🙂

      Love, Hannah


  2. Casual doesn’t have to mean leggings or slacks. A denim skirt, top and cardigan can do that just as well. A pair of flats, be they ballet flat, tenners, sandals, or what have you can go as well as a low wedge for the casual look.

    But, I agree, if we are only out a few days a month, the dressing up is more attractive. I do try to keep it to blending in if I’m going out shopping, especially to the malls, but if it is a night out with friends for dinner, clubs, or even meetings, then I’m more willing to dress up.

    Liked by 1 person

  3. Formal or casual: I think it’s all about finding clothes that work for you and that you feel great in

    If you’re worried about shoulder bulk, have you had a look for tips on hiding big shoulders? BTW, I don’t look at your photos and think ‘big shoulders’, but I think I get your concerns too.

    How about a dark top, skinny jeans, and flats? Or a tunic with leggings? I think shopping for a new look can be great fun. There’s always the wedge sandal if you’re not prepared to give up on heels 🙂

    Liked by 1 person

  4. Tunics and .leggings can definitely be a fun feminine outfit … especially when it starts getting cold out. Add a long cardigan and accessorize with a pretty scarf. Skinny jeans with a pair of cute booties is also a nice casual look. Sometimes you have to go with what the destination calls for. I love a dress and 3 inch heals but where I live the typical outfit is jeans and sweatshirts. I try to live on the nicer edge but not stick out too far. Love your blogs!

    Liked by 1 person

  5. Hannah- Just mt 2 cents worth but I think the sweater, short skirt and boots looks wonderful and would serve quite well as a start to the occaisional outfit that you are talking about. Don’t forget that accessories can upgrade most any outfit.

    Liked by 1 person

  6. Hannah, I would NEVER try to give you advice on style, but I agree with some of the other gals that you would look fab in a girly outfit of tunic and leggings. The part of this post that struck me the most was your comment that you feel just as comfortable in a suit and tie as you do in a dress. Although these days I don’t often wear a suit, when I must, I’ve felt increasingly uncomfortable over the years as my GD become more pronounced. I end up feeling “in costume,”and can’t wait to get it off. Admire your fluidity! Nancy


  7. Fun and interesting topic!
    I love “dressing up” which for me always includes a beautiful dress, pantyhose and heels. I have so many other outfits that I hope to wear in the future, including finding and wearing a pretty wedding dress.
    I’m sure you’ll will look great in whatever you wear and will appear confident and dignified. You are a tremendous role model and advocate for our community.

    Liked by 1 person

  8. Hi Hannah, I really enjoy your posts and emails.  I also like your emphasis on feminity as opposed to just sex.  I am a mature, long-time CD who does not get out much.  But, my wife will be gone for three weeks beginning in late October.  I’ve always wanted to go the Townhouse on a Saturday night, but have not had the courage to go by myself.  Is there any chance that the MN Tgirls will be making a visit there during this time?  I would love to join you.   Claudia Rinaldi


    1. Hi Claudia, thanks for the kind words! The MN T-Girls do meet once a month but this month’s outing will not be at the Townhouse. However, there’s always a chance individual members may choose to drop in on any given Saturday. Have fun!
      Love, Hannah


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