Why Women Feel like they Can’t Wear the Same Thing Twice

Amber Poe
6 min readFeb 13, 2024
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So first I want to clarify something right from the beginning because I know inevitably the first comment if I do not clarify this from the beginning will be something along the lines “Of course women can wear the same thing twice, how dare you make clothing some rich commodity! Clothing is utilitarian and how dare you suggest this!” Yes, you are 100% correct. You can very well wear the same sweater and sweatpants every day or the same dress or skirt or collared shirt or jacket every day. I am not here to suggest that you cannot, I am only here to elaborate and attempt to explain WHY women feel like they cannot wear the same thing twice.

I believe I have a very unique perspective on this having transitioned from male to female. When you have an outsider’s perspective to something, it easier to see the obvious staring you in the face. Admittedly, I was like most men who work in an office. I had bunch of collared shirts albeit long or short sleeve depending on the season, dress pants/khakis: two in black, two different shades of brown and one shade of white. Men’s fashion is pretty simple. Black and white for the most part go with everything and the shade of brown I would mix with another earth tone or a solid white collared shirt with possibly a tie if I have a meeting that day or am with clients.

What people didn’t know is I often just wore the same five sets of pants in a rotation for a week cleaning them on the weekends (assuming they didn’t get a stain on them so they stayed in rotation). After all, just grab my febreze bottle and lint brush, hose it/wipe it down, let it dry for the next day and grab a new collared shirt in the morning with a possible tie, throw on black shoes with my same black peacot and boom, you look business presentable. No one ever said a thing because a) men don’t care and b) women don’t care either. Just so long as you look presentable it’s acceptable to both men and women (oh and showering is a must haha).

Sooo what about women? Why can’t they wear the same thing twice…scratch that. Let me rephrase this…Why do women feel they cannot wear the same thing twice? Well let’s start with the obvious. Women inevitably have to be around men at some point each day for the most part. Albeit at their jobs or at home with their husbands/picking their kids up from school and seeing the teachers/other parents/neighbors/sporting events/community get togethers/etc. And what do men do the most to women? I’ll give you a hint, it starts with the letter “J”.

Men LOVE to judge women and this is obviously not a new thing as it’s pretty much gone on throughout human history. Men judge women on any number of things but let’s state the obvious: what they’re wearing, their figure, their makeup, their hair, their demeanor, whether or not she smiles or is confident or too confident (need I remind people of the Barbie movie speech on how difficult it is to be a woman?) Men will just blurt out the first thing that they notice “How come you’re wearing the same thing as yesterday?” or “Is that the same perfume as yesterday?” or “Why are you wearing sneakers and sweatpants all the time, why don’t you wear something sexy like high heels and and a dress?”

Shall I go on? I think I’ve proven my point but here is where my unique perspective comes in. Becoming a woman I inherently have to learn from somewhere and the real world is where I’ve done most of my learning. I noticed as with the increase in HRT and my hormone shift, so did my way of thinking (for the better I might add). With that mode of thinking, I immediately started to notice other women’s hair, nails, makeup and yes their clothing attire. When the dysphoria was at an all-time high which coincided with me not having socially transitioned yet, I found myself envying women for all that they are able to wear and their options. It drove me beyond crazy and I have touched on this in some of my earliest articles that I have published.

Now that I am socially transitioned and have worn women’s clothing on a daily basis, when I see some women’s clothing or even shoes I immediately think “Ooh I would totally rock that, I hope they have that in my size!” But that was early on. Now inevitably I find myself comparing myself to other women and what they are wearing. For example, if someone else is wearing jeans, why does her top look more put together than mine? Why do those shoes match so well and mine don’t? Ughh!

The second answer to the question of why women don’t feel like they can wear the same thing twice is because of women! Women innately judge other women just as bad as men and possibly worse…and I haven’t even gotten to name brands of things. Why does she have a Coach bag and I have a Walmart purse? Why does she have a Valentino dress and I have a dress from Target? I have red soled high heels that I got from Teemu but they’re not Christian Louboutin ones. Women inevitably compare everything and if she doesn’t say anything I can bet you she is thinking it. And if a woman wears the same thing twice let’s say within a two weeks span, she gets in her own head probably thinking “Oh my god, what if someone notices I wore the same top…I have to at least wear different pants or shoes…what if someone asks why I am wearing what I wore awhile ago???”

I NEVER used to think like this as a guy. I feel as if there is this innate pressure to always mix it up and then I get in my own head about it, overthink things and then before I know it, I’ve tried on a skirt with a blouse, dress pants with a simple top/peter pan collar to finally jeans and a sweater. I am constantly going over in my head the combinations to mix and match. Oh…and I haven’t even gotten to seeing what footwear I am going with so the whole ensemble is cohesive. Should I wear jewelry, what kind of makeup routine am I going to go with…oh my god, I forgot to do my hair!

I can finally now see why there are a ton of different chain gently used women’s clothing stores and basically just a Goodwill / Salvation Army for men. Women are in a constant state of turnover for clothes to avoid wearing the same thing in my estimation about three (3) times. Plus you can only mix and match certain things until in your mind the combinations run out and it’s off to the gently used clothing store or Goodwill. Men will literally have five (5) pairs or even let’s say ten (10) pairs of pants, doesn’t matter how many mixed with twenty collared shirts and they last for years. When I was purging my male clothing, I basically over the course of my male life had about eighteen (18) collared shirts and about nine (9) or ten (10) mix of dress pants/khakis that I accumulated over the years. That’s it because no one really cares what men wear, lol. Again, I NEVER used to think like this as a man.

I will end this on a fun note and I am sure many of you have seen this meme of Tom Holland aka the actor who plays one of the Spidermans in the Spiderman series. I feel this way ALL the time now and this is now 100% true to me now. As a guy I would literally just wake up, grab a pair of the cleanest pants I have, find any old semi-matching shirt, throw an undershirt on, belt, pop some shoes on and be out in five (5) minutes. Now I spend at least ten (10) minutes the night before planning my outfit for the next day and then when I finally have it on and it doesn’t look right, I have to change on the fly because I may have worn this top last week and in my mind that’s the end of the world when in reality it’s all in my head.

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Amber Poe

I am a 42 year old AMAB who is 18 months on HRT to become the woman I always destined to be.