QuoteThere is a transwoman at the place where I buy coffee. She's quite tall and is easily clocked, but I love her style and regardless she looks so feminine and pretty.
I really want to introduce myself, but I don't know how without making her feel strange.
I am quite jealous of her, because she's out and wears the cutest outfits, and looks so feminine.
Any suggestions?
Apologies in advance for the long, detailed reply! Thanks for sharing this and asking this forum instead of taking it upon yourself to make assumptions and just blatantly "ask something" simply because you're curious! I couldn't agree more with all of the responses here, the main one being
never make assumptions. You could certainly be right, but you could also be wrong, and then both parties involved could wind up hurt. Nobody wants that!
Just to preface: I'm in the USA (Ohio, to be exact) and it's a bit different for me since I
am a transwoman and that can make it a bit easier to approach the subject (and I don't mind sharing that about myself or educating anyone about it — I wear it on my sleeve even if I'm not "clocked" — since I'm getting older and really don't care what others think of me, just what I think of myself, haha — but this is surely not the case for everyone!). Ironically, I used to manage a Starbucks and also worked at another (local) coffeeshop in my early 20s for a few years (basically, a few years after coming out myself). I only mention all this to say that I have had many conversations about being trans specifically (i.e., my journey) and in general, and also have encountered both uplifting and disparaging remarks about it.
Again, I applaud you for being sensitive enough to ask this question here first. If you can't do it in a forum full of trans people, where can you do it? Ha ... Anyway, I've been asked this question a lot of times by cis/straight/het-norm friends of mine when they want to display their allyship or show kindness and support or even become acquaintances with someone they think may be trans or nonbinary, etc. either because they work with them, see them often (which seems to be your situation), or serve them in a restaurant or store often, etc.
This may require
several conversations over the course of time, which I recommend, but my best advice to my friends and to you is to simply introduce yourself with a simple follow-up — like, "Hi, I'm Sasha, and I just wanted to introduce myself since I've seen you in here a lot and I also come here a lot." It's innocuous and the other person typically reciprocates. Then, based off of how they respond and their tone, you could begin a conversation with a general statement, like, "I really enjoy the atmosphere here, how about you?" and then possibly an uplifting statement regarding them, like, "Oh, and by the way, I really wanted to let you know how much I admire your style!" (I've also worked in retail for many years and honestly never encountered a person who doesn't like hearing praise like that, especially when it's a blanket compliment like that which comes across as honest and heartfelt.

)
There are SO many things to talk about before the gender discussion is even raised (and a little self-deprecation never hurts), like, "I'm a pretty basic customer and always order a regular coffee. Do you have a favorite drink (or food item, etc.) here? What do you typically like to order?" Follow the conversation. Depending on their reception of you, you could segue into something like, "I really like your necklace (or blouse, etc. — nothing that isn't visibly presented, mind you). May I ask where you got it?" (Just try not to come across as "creepy" and just let the conversation flow naturally. If things are going well, you'll most likely be able to sense it.) Or, rather, you could save this for your next conversation (same with what I said above about liking their style) since you mentioned you see them a lot at this coffeeshop. Again, I'd definitely suggest that. Essentially, after you've established a basic rapport with them, that's when it's okay to start with the "particulars." Conversations generally flow more easily over time, especially after the person has gotten to know a bit about you, so I really do encourage you to go about this after a series of brief conversations while opening up a bit about yourself along the way. Being as open as you can about yourself invites the other person to let down their guard and can lead to a sense of comfortability.
If they introduce themselves back to you and engage further in conversation for a bit, or after the course of a few conversations (which once again, I highly suggest since you see them often), then (in my humble opinion) I'd imagine it's pretty safe to say that you can
politely ask what pronouns they use, provided you do so with an accompanying statement like, "I don't mean to overstep here. I'm only asking because I would never want to assume anything on your behalf and only ever wish to be respectful toward you." Just make sure you've built a rapport first and try to keep it as generic as possible because, like everyone, there's far more to someone than simply their gender identity and you don't want to come across as if that's the only thing you care about. (And I'm hoping it isn't in this case!)
In all honesty, when my friends have followed this advice/approach in the past, they've generally gained a new friend and both parties are thrilled (about 95% of the time), which could very well work out to be the case for you. But, as others have said, just be very careful and sensitive, especially with your wording and body language. If you're respectful and kind, they can sense this and may even answer your questions without you even having to ask. Just keep that sensitivity gauge at the highest level possible and don't dive right into the gender conversation head-first! As I mentioned, just like you, there are far more facets to a person than simply their gender identity, and multiple conversations (short as they may be) are recommended.
Again, PLEASE take this advice with a grain of salt (and combine it with all the other responses others have provided) as it's coming from a transwoman who's been out for a couple decades and who is completely open to any and everyone who asks me anything and who simply has a desire to educate folks and spread love and awareness.
The fact that you posted this seemingly indicates that you want to be sensitive and that you don't want to come across as presumptuous or condescending — and if you do this and do it properly, this person will be able to sense that. The fact that you mentioned they are "quite tall and easily clocked," along with everything else, likely indicates (to me at least) that this person is courageous enough to accept who they are in order to present this way and has probably encountered FAR worse than what you could say. It also indicates that they view this coffeeshop as a safe space for them, so please be very aware of that. If this individual is actually trans, then speaking for myself and my own trans friends, all we ever really want from others is respect, acceptance, and maybe even some validation. A little praise and admiration never hurts.
I really think the most important thing here is to simply interact with this person just as you would anyone else. They are a person just like you or I am and no different simply because they may (or may not) be trans. And if they are, in fact, a transwoman,
they are a woman! Period, no question. Like myself, just because I'm trans, that makes me no less of a woman! Just don't assume anything. Validate and uplift the person. Show respect to the person. Display a genuine care for the person. People who take that approach typically receive responses of a similar nature. There's a lot of nuance to this, so best of luck to you!

If after talking to them, it seems like they have walls up, then just leave it (and them) alone. Just be kind and be careful!
(And for those of you who may disagree with me here, I apologize and please don't jump all over me! I am more than open to being corrected. I know that all of us are different. I'm simply sharing the approach I've suggested to folks that seems to work best based on a vast span of years of anecdotal experiences. What I've proposed here has seemed to function well for many of my friends over the past 20 years and I'm only sharing it in the hopes that it will function similarly in this instance, assuming that rapport is first established and that respect, support, and an uplifting nature are all demonstrated to this individual by OP over the course of time. My intention is absolutely
never to disrespect anyone or their personhood, beliefs, and character!)
Much love to everyone as always! <3