Firstly, read Halimede’s gift guide. She’s a parody account but her advice in this case is largely quite good.
If your particular trans woman is not in one of her categories though, consider the following ones:
Gifts for the trans woman who…
For plural trans women, the first thing is determining how separate and distinct the system is. If they're distinct and separate you shop for them like individuals. You may not have the budget to cover shopping for all shards simultaneously though; in such cases you should pick a commonly fronting system member to give something they really enjoy and that ideally the rest of the system will get some use out of, and rotate through the common fronters.
For blurrier or more median systems you're probably better off pitching gifts to themes in their collective personalities.
A lot of systems develop personal mythologies/backstories or nonhuman associations for their shards, whether they're fictives or not. Gifts that are associated with a shard's personal aesthetic are likely to land well.
Some systems may have difficulty holding on to memories or emotional contexts. Keepsakes and mementoes of experiences can help trigger old memories and keep old joys fresh in their minds. You might also consider getting them a nice journal - Paperblanks has some gorgeous designs - to record important things in, particularly if they have an artistic bent.
One of the best gifts you can give a system is to listen to their history as a system and get a better model of each shard individually. Many systems are used to being rounded off to a singlet by most people they encounter, even people they’re out to, simply due to the complexity of their personalities taking time to interact with. If you have the kind of relationship where you can ask after particular shards' histories or backstories, this is a good opportunity for bonding - and will give you ammunition to give suitably aesthetic gifts.
Do be gentle though and take no for an answer; shards' backstories can involve dark memories, particularly in traumagenic systems, so if your friend or loved one seems reticent, don't push.
A lot of trans women feel that they’d like a do-over on their childhoods. This may show as age regression, a desire to constantly be puppy/kitty, or other “childish” preoccupations. A lot of trans girls are under constant pressure to perform adulthood, so one of the best things you can do is show them that you support them regardless of their mental age. Adult coloring books are a good gift here, ideally on a theme your giftee enjoys. Cute plushies and candies are also good picks. You might also consider getting her a pair of pink arm warmers or striped thigh-highs. Cat ear headphones are also a fun option. Some regressors swear by lego or other forms of model kit — as usual, knowing your giftee is likely to matter significantly.
If they have a sona, furry or not, art of it is likely to be very enjoyed. Consider hiring an artist. However, for closet furries a true fursona is less likely than a human character with animal ears. Yes, there’s a difference.
A pair of custom animal ears might go over well — consider getting a pair off Etsy for the specific animal your giftee associates themselves with. Good quality ones will come with tassels or other ear jewellery built in. Anything branded with an associated animal that they'll actually use is good — stickers to put on their devices make a good stocking stuffer, while plushies and mugs with appropriate designs will get the job done. You can also just gather artwork or photographs of their favorite animal for them to look at and enjoy!
You might also consider getting them the excellent transformation/sex VN Mice Tea, or its sequel Coffee Buns which is available in beta builds for patreon subscribers.
Get her art of her fursona. If she has a model sheet for her fursona, use it.
If she hasn’t played Mice Tea, get her Mice Tea. Seriously, it’s got two canonical trans women out of four character routes. If she already has Mice Tea consider getting her one of its sequels by Cinnamon Switch. If she hasn’t heard of Patricia Taxxon consider getting her into Taxxon’s more approachable music. It’s like someone’s scrawling letters on your brain, in a catchy way.
If you have the kind of relationship where sexual media is exchangeable, consider getting her an erotic VN. Heart of the Woods and Highway Blossoms both are strong candidates with optional sex scenes. Make sure to tell her to apply the free adult patch. Mice Tea again. Ebi-Hime's spicier visual novels, once again with the adult patches. Hardcoded. Consider also offering sexual favours if you have that kind of relationship and the personal stamina to make good.
If she’s blatantly horny on main but you don't feel comfortable sending her pornography, consider offering praise or personal attention instead — many such trans women are chronically touch deprived, and any form of connection helps.
Doll-joint stockings and/or arm-sleeves may land well here. Consider also giving her an old and elaborate-looking key strung as a pendant, or a nice tea set. You will be marked on how deep an aesthetic gesture you make and how original your sentiment is. Do your best anyway.
Get her cute computer accessories. Stickers to put on her desktop tower or the back of her laptop, a desk mat in a theme she enjoys, or if you want to really treat her a high-quality mechanical keyboard. If you get her a computer peripheral she is likely to want a corded version rather than a cordless version; wires are just less of a hassle than any battery powered device for someone who’s truly heavily online. Ask her if she likes pink things. (The answer is probably yes but be sure.) Also check it out on RTings before you commit; don’t get her a piece of pink junkware.
If she’s the type to fiddle with every little setting, introduce her to Rainmeter for more extensive desktop customization. If she runs linux she’s above my level and probably above yours too. Don’t fuck with her setup; get her something to make it prettier instead.
She also might not own a controller for controller-based games if she predominantly plays with keyboard and mouse. Consider getting her one.
If her hands hurt from constant typing and scrolling, consider getting her more vitamin C; Vitamin C deficiency can result in easier RSIs. Magnesium supplements might also help. Also consider getting her a standing mouse.
Get her a SAD therapy lamp if she doesn't have one, seriously, it will help and she is unlikely to purchase it herself. Consider also raising salt intake, spironolactone has consequences.
Moving on from medical interventions, consider getting her a RGB LED nightlight for her bed. On red this will help her sleep better, and give her the ability to see her room at night without needing to turn on a big bright light that makes getting back to sleep difficult.
Plushies also help, as does anything under the heading of comfort food. Good quality chocolates can go surprisingly far. If she has a meditative activity she enjoys, give her the tools to do it privately and uninterruptedly.
If she somehow hasn't played Celeste, get her Celeste. But she probably has played Celeste.
Consider also giving personal attention and time. Sex is also a good mood booster if you have that kind of relationship.
Find an activity that she is good at and enjoys and give her the ability to pursue it. Personal attention is also useful here, but what you really need to do is show her she's 1: capable of doing difficult things and 2: appreciated for herself as a person, and that's a long term struggle.
Give her honest praise. If she has an artform or craft, commission her on a generous deadline and follow through on paying her for the piece. Treasure it as much as you honestly can. This should not be hard if you honestly believe in her.
See also the section on feeling sad — many of these problems have common causes. It's hard to feel confident when you're emotionally torn up.
Many of the rules are the same for autistic trans women as they are for ADD trans women. Focus on her comfort; a lot of the time neurodiverse people are constantly pushed into situations they’re ill-equipped to handle, so gentle support is good.
For ADD women, avoid planners, schedulers and timers - all of these are likely to have been used against her by family or teachers. Gamification applications may see better uptake but aren’t generally good gift material. Instead give fidget toys, weighted blankets, good-quality headphones or earbuds, and whatever her current preoccupation is this week. Some ADD women may have particular items on their radar already, but be hesitant to commit when so many of the things they buy go unused due to disorganization or distraction; consider asking what they think is shiny in new releases.
For autistic women, the advice is similar, though their special interests are likely to be more enduring. Avoid etiquette books, and if they’ve been exposed to the worse kinds of “therapy” they may also have reason to avoid headphones. If you take the time to get into the minutia of their special interests you’re likely to find something good for them, and you might learn something while you’re at it. If you can find cozy garments with good textures and no tags they’re also likely to thank you. Avoid scratchy fabrics and anything that pills; these are a sensory nightmare.
For both categories, be especially careful not to create a relationship of obligation between you and them to try or use a gift. Neurodiverse people have little enough spare energy without dealing with that kind of social obligation. Don’t get them that $500 video camera based on their previous interest in videography from three months ago. Just don’t do it.
A lot here will depend on the exact circumstances of their family.
If the family is reasonably good, most of the options in this guide will work, modulo some concerns regarding discreetness of sexual gifts. Maybe don’t get her a Hitachi; the sound carries.
If the family is controlling, you may have to get creative. The safest gift in such circumstances is one the family is not aware of; digital gifts are good for this, as is anything pocketable. If the circumstances are seriously bad, the first priority should be getting your giftee a texting-capable phone so they can organize an escape. If your giftee has freedom of movement outside the house and is in an urban area, you can have your gift delivered to an amazon locker while they’re out and concealed in a habitual bag or purse to bring it back to the home. In rural areas you’ll have to rely on snaffling the package before the family notices; frequent tracking updates are your friend here. Gifts of money or gift cards may be able to circumvent this whole process to some degree, though your target may have a joint bank account with their family still - be cautious about depositing money to a bank balance that may be monitored.
It’ll be okay. Most trans women do get out of shared living situations with their families eventually. Support from the broader trans community can be majorly helpful in hard cases.
Gifts from this section are likely to be a little more sensitive, but if you happen to be an older trans woman buying gifts for a younger one, or otherwise in a mentorship role, items from this section may punch above their weight class.
Firstly, facial hair. This is a major source of dysphoria for many trans women. If she does not own an electric razor, get her an electric razor. It will help make shaving less of a chore and give acceptably-good results as long as her hair is not very dark. A waterproof one is ideal so she can use it in the shower. Black-haired trans women may need a closer shave than an electric razor can give; these cases are harder, unfortunately.
If she has an electric razor or other shaving solution already, consider paying for laser or electrolysis to get rid of the issue for good. Gift cards for sessions are offered by many clinics, and many trans women struggle to get the funds together to pay for the procedures because it’s considered ‘cosmetic’ by most insurance companies and governments.
If you can’t afford either of the above options, get her some fancier soap - LUSH sells good options in this category. I’m particularly fond of their honey soap. If she has curly hair and wants to grow it out, consider learning how to braid her hair and/or teaching her how to do it herself. A big pack of scrunchies can also help tame hair and make it easier to grow out longer. Getting her a pack of scrunchies in many colors is a good way to learn which ones are her favorite.
V-necked shirts are likely to show off her good qualities and reduce the apparent profile of her shoulders. Also see the next section on skirts. The stereotypical striped stockings help a lot of early-transition trans girls, so consider getting her a couple pairs.
If you’re in a position to be a major force in her life, getting a gift that makes it clear you find her beautiful is a good way to make a serious impact. The sentiment coming across clearly is most important here; consider a keepsake bracelet.
(And really, don’t we all?)
Casually gothy and asian-influenced styles are more likely to land. Witch Vamp is a good option if you are in the US. Blacks, reds and purples are conservative, while pastels are likely to be considered daring. Some may adopt a more cottagecore aesthetic and be willing to indulge in a brown or green, but this is less common. Some trans women have very distinctive personal aesthetics; if they have a known style, pick something that fits in. Get her something with pockets; most trans women are used to them from their previous lives in menswear and will not wear skirts with no pockets. More conservative maxi skirts may be a better fit for trans women who feel insecure about their bodies.
Write her a personal letter. It does not matter what is in the letter so long as it has a positive overall tone. Long-form letter writing is a dying art and it is one of the easiest ways to make a connection with someone new, because the longer format and time to compose it means you're more likely to cover deeper topics. Consider also doing the Rice Purity Test or similar other online quizzes together.
If you want to court her seriously, make your intentions clear up front and allow her the choice of whether to engage. If you've produced a good impression you're likely to make progress.
If you have already reached the point in your relationship where you talk regularly, consider sharing more of your daily life with her. You can only engage so far if you try to keep your day to day unknown. Texting is your friend here; liveblogging your day is likely to interest her and keep her engaged.
If you want to make it clear that you are serious about the relationship with a gift, give her something of yours that you treasure, ideally from your childhood, as a memento of you. Ideally this should be in the form of an exchange with a similar object of hers. If you don't have one you can make one, but ideally it should pass through your hands on its way to her. Matched (or mismatched) necklaces are particularly good, especially if the implication is that it is a reciprocal day collar. Plushie swaps are also a good option.
Before anything else, make sure the communication link between you and her is secure. Set aside money for computer or phone replacements. You can't have a working relationship with someone you can't contact.
Get her a representative plushie of you so she has something to hug when thinking of you. Anything of yours that you can mail her is likely to be treasured by her even if it's not very impressive. Digital goods such as video games and ebooks are likely to be your stock in trade, but once you exchange addresses more physical gifts are better because they remind her that you are not just words on the screen but an entire other person. Consider recording her messages of your voice that she can play when she wants to hear you and you're unavailable. Saying "I love you" out loud goes a long way.
Then use everything in the "hope to get closer" section and do your best. It'll be okay.
While trans women certainly face challenges in their everyday lives, it’s amazing how much you can improve their lives with a well-selected and well-intentioned gift. By taking the time to consider and accommodate your giftee’s preferences, you can make their world just that little bit better - and isn’t that the point, after all?