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
Hannah McKnight 
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.
Love
Nicole
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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
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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.
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Thank you! I have been meaning to get a denim skirt.
Love, Hannah
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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 🙂
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Thank you for your suggestions! I actually wear “girl” jeans in male mode, but I like your idea of a tunic and leggings.
Love, Hannah
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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!
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Thank you! I think I need to hit the mall this weekend!
Love, Hannah
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A nice pair of jeans and a sweater can be very feminine, and you can do just about anything with the shoes and still feel “right”.
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I think you can do ANYTHING with the right pair of shoes. )
Love, Hannah
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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.
Donna
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Thanks Donna! I do need some new skirts.
Love, Hannah
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You can definitely pull off a long sweater or tunic over leggings…and heels would be perfectly OK with that combination.
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Thank you for the suggestion! I think that sounds cute.
Love, Hannah
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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
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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.
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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
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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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