Gender Affirming Fashion That Will Actually Make You Feel Hot

Gender affirming fashion is a crucial step for us to feel aligned with our gender. Fall is the perfect time to step up your wardrobe and experiment with layering, textures, and playing with our silhouette.

Right now I have been feeling particularly drawn towards the bimbo aesthetic, being dressed unapologetically sexy. Additionally with spooky season being upon us I tend to gravitate towards goth and punk aesthetics, Taylor Momsen being my biggest influence at the moment. Another style inspo of mine at the moment is Madison Montgomery in AHS Coven.

This post is for the girls who aren’t afraid of being seen when it comes to the outfits they want to wear. And if you’re not there yet, maybe this post will give you some ideas to have fun with your style. To take more fashion risks, to truly enjoy self expression as a woman. We all deserve that.

Cool Trans Girl is about being your best and sexiest self so I’ve compiled a list of 8 different outfits I’d for fall but also give main character bad bitch energy. Also all of this stuff is from Amazon which I may get a small commission for if you find anything you like 🙂

Table of Contents

Gender Affirming Fashion: Outfit #1

A Taylor Momsen Inspired Daytime Outfit

Gender Affirming Fashion Apparel

Oversized Graphic T-Shirt

I’ve been really into wearing oversized clothes lately, like this T-Shirt. It makes feel like Ariana Grande and sometimes leaning into androgynous styles can make me feel more gender euphoric! I love wearing a big t-shirt as a dress and then leaning on accessories to give it a rockstars girlfriend kind of feel.

Vegan Leather Jacket with Sherpa Lining

This oversized leather jacket is perfect layering piece to wear with a big t-shirt! It will still give you that very youthful aesthetic while actually providing warmth and comfort. I’d recommend sizing one up to ensure the fit isn’t too narrow.

Thigh Highs

Okay I know these thigh highs are literally so cliche but there’s a reason trans girls love them! Not only are they so hot but they are a super easy and cheap way to level up your outfit! When I was looking at Taylor Momsen’s Personal Style I noticed she wore a lot of hosiery and I’m looking forward to making this a part of my gender affirming fashion tool kit.

Garter Thigh Highs

These garter belts are so hot and will go with your thigh highs perfectly! These just add another fashion detail that will level up the oversized t-shirt and make your outfit look more intentional. Not too mention they’re super sexy, hence why this is a great item to include in your gender affirming fashion looks.

Black Platform Boots

These super edgy black platform boots are the move for F/W 2023! Coincidentally, in the most recent Christian Cowan show (where that big ball of fur got lost on the runway) all the models were wearing these EXACT boots! Not only are these boots a gender affirming fashion find, they’re high fashion baby!

Oversized Sunglasses

These oversized black sunglasses say, “don’t talk to me.” And I love that. I also love oversized sunnies for when you need to leave the house without makeup. Also huge sunnies are inherently glamorous and feminine which is why I believe this is a gender affirming fashion staple!

Spiky Choker

This choker just ties this whole look together! For fall winter I want to be wearing chokers non stop, chokers not only feel super feminine but they come in so many flavors. In this case, the direction we’re going in is super edgy. Chokers are super sexy and are great for the bedroom too 😉 That’s why chokers this season are a fun gender affirming fashion choice!

Black Hobo Bag

This black bag is perfect because it’s so versatile! Not only that but I’m seeing a huge revival in the oversized hobo bags from the mid to late 2000’s. Think literally every purse that Serena and Jenny wear in Gossip Girl. These bags also make me think of my aunties in the 2000’s which is why I believe hobo bags are the moment for fall, but also a super gender affirming fashion choice.

Eyeliner Pencil

Pencil eyeliner is a must have for fall makeup looks! The girl who wears this outfit I imagine carries a pencil liner everywhere she goes to touch up her eyeliner from the night before. Eyeliner is such a fun and versatile makeup tool that every girl who loves makeup should learn, hence why this an essential gender affirming fashion tool.

Liner Sharpener

I keep one of these pencil sharpeners in my purse at all times! Nothing is worst thank being stuck with a broken lip liner or eyeliner when you need it the most. Even if you don’t opt for this one, a pencil sharpener is a makeup bag essential that can cost as little as fifty cents.

Taser Gun for Self Defense

Were not fucking around with this taser gun! All CTG’s should have a self defense tool in case they end up in a scary situation, god forbid. But there are some sickos out there. This isn’t so much a gender affirming fashion choice but a reminder for us to make sure we can defend ourselves.

Gender Affirming Fashion: Outfit #2

A Day-to-Night Downtown It-Girl Moment

Gender Affirming Fashion Apparel

Leather Maroon Corset

This vegan leather maroon corset top is so hot!! It kind of gives coyote ugly meets true blood vibes. I love a corset top because it not only snatches you in but can give you some cleavage if you have small boobs. Hence why I love wearing corsets, they’re one of my favorite gender affirming fashion choices.

Grey Mini Skirt

This grey low rise mini skirt is a must have for fall! Okay so this is definitely a knock off of the brand “Nodress” where you can expect their skirts to run around $200. Low rise mini skirts are so so hot still and just because it’s getting a little chilly doesn’t mean we want to give up skirts all together. So hence why I wanted this feminine skirt to my list of gender affirming fashion staples.

Black and White Fur Jacket

This jacket brings all the drama! When I saw this jacket online after trying to style the skirt and top combo above I literally gasped. Not only does this jacket look super warm and cozy for fall, it adds the perfect amount of contrast while still pulling the look together. Faux fur is not only a cheaper and more ethical choice but it gives your outfits a bougie vibe. You will see a lot of faux fur on my list of gender affirming fashion choices.

Gender Affirming Fashion Accessories

Balenciaga Knockoff Boots

These boots are so c*nt! I was like woah the turn around time for these balenciage knockoffs to end up on amazon was pretty quick lol. Boots can help elongate your legs while you’re wearing mini skirts to give you a model-esque look. Plus heels are actually found to make women feel more confident, that’s what makes these a gender affirming fashion choice.

Rose Choker

This red choker matches the corset perfectly! Not only that but the rose adds another super feminine detail to this already super c*nt outfit! The super sweet detail element this adds to this outfit is a fun gender affirming fashion choice.

Zebra Clutch

This clutch is such a statement piece! I actually was debating whether or not to keep this clutch on the mood board when I found the perfect jacket but there wasn’t any other bag I thought did the outfit justice. Plus animal print is super c*nty which is why I think this is an amazing gender affirming fashion choice.

Self Defense Alarm Keychain

This is an alarm for a situation that would require self defense! Having this tool in conjunction with another self defense tool like pepper spray is a best practice in my opinion! More than likely you’ll scare off any sickos and you’ll alert anyone who’s nearby! Also it may buy you some time to think quickly if the situation escalates.

Animal by Lisa Taddeo

This book is unhinged! Not only that but it’s my favorite fictional book at the moment! The synopsis from Goodreads is as follows, “Joan has spent a lifetime enduring the cruel acts of men. But when one of them commits a shocking act of violence in front of her, she flees New York City in search of Alice, the only person alive who can help her make sense of her past. In the sweltering hills above Los Angeles, Joan unravels the horrific event she witnessed as a child—that has haunted her every waking moment—while forging the power to finally strike back.”

I Bring Nothing to the Table by She Ra Seven

Goddess Shera Seven has spoken! Sprinkle Sprinkle! As women it’s important to not let men take advantage of our yearning to be loved and accepted. This book has changed my life and has helped me repel dusty tranny chasers who have no intention of treating me like a princess.

Italian Vogue

Italian Vogue is one of the best Vogues! I’m sorry but American Vogue is tired! This high fashion streetwear look I put together looks like it would be worn by a girl who loves reading Italian Vogue. Plus you’d be able to find inspiration for other gender affirming fashion looks!

Gender Affirming Fashion: Outfit #3

Indie Sleaze Brooklyn Baddie

Gender Affirming Fashion Apparel

Crop Graphic Tank Top

This graphic top is so cute! Not only that but it’s a versatile and edgy piece that’s a great base layer for jackets. The cropped fit and safety pin details give me Bratz doll vibes which is why I’ve included this in my list of gender affirming fashion choices!

Snakeskin Leggings

These leggings are not for the faint of heart! They’re so loud and in your face and were honestly the starting point for creating this indie sleaze outfit! Leggings are a staple of indie sleaze outfits and I’ve noticed more girlies in NYC starting to wear them. If you like being a trend setter than this gender affirming fashion choice is for you!

White Snow Bunny Jacket

This fluffy white jacket is so iconic! I love the contrast of white against the black top and snakeskin leggings. I feel this just ties the whole look together. Not only that but when winter comes around you’ll be able to style this jacket and have a little snow bunny fantasy. This fluffy jacket is def a super bold gender affirming fashion choice!

Gender Affirming Fashion Accessories

Metallic Blue Pumps

These royal blue metallic pumps are everything! These will help elongate the legs in those leggings, I would strongly recommend not wearing boots with those leggings. It could potentially make you look shorter and the proportions would just be off. Pumps are always a safe bet for gender affirming fashion!

Sexy Bling Choker

This choker is sexy! Literally lol. With indie sleeze more is more but I feel this elevates the look and gives the outfit an elevated feel. Plus wearing anything that says sexy surely makes this a super cute gender affirming fashion accessory.

Dollar Sign Earrings

These money earrings bring the fantasy to life! You might want to slick your hair back or tie it up in a ponytail to avoid tangles. The tacky opulence is definitely a trait of indie sleaze style. Anything sparkly is automatically a gender affirming fashion choice!

Silver Sequin Clutch

This sparkly clutch is like so fetch! I also love the movement this add to the outfit! It’s a fun eye catching detail. Clutches are super feminine and great for a night out which is why I always love having them around as a gender affirming fashion accessory!

Oversized Sunglasses

These oversized sunglasses are a moment! I imagine the girl who wear this outfit would be at the club wearing sunglasses, not to be a c*nt but she took an edible before she left the house and she doesn’t have eyedrops. Big glasses are always a gender affirming fashion choice!

Liquid Liner

Get the perfect cat eye with this pen from stilla! I just know liquid liner would just add to the drama of this outfit. Eyeliner is one of my favorite gender affirming fashion details to add to your going out look!

Liquid Lip YSL

This lip from YSL is the perfect red!! With an intense eye look you may not want gravitate towards red but this look is already over the top so why not lean into the fantasy even further? Red lipstick is super c*nty which is why I consider it a safe gender affirming fashion choice!

Knuckle Ring

This ring doubles as a gender affirming fashion statement and a self defense tool 😉 Three finger rings are such a reflection of the indie sleeze era but you could also punch a creep in the face if you needed.

Gender Affirming Fashion: Outfit # 4

A Witchy Day-to-Night Look Inspired by Madison Montgomery

Gender Affirming Fashion Apparel

Shaggy Faux Fur Jacket

This shaggy faux fur jacket is an elevated statement piece for fall. The shaggy texture adds a lot of movement which adds to the drama. Not only that but it looks pretty witchy (hence why this outfit is directly inspired by Madison Montgomery. If you channel her in your outfits you can be guaranteed to create a gender affirming fashion look!

Silver Sequin Hot Pants

These silver hot pants are so in right now. All the fashion girlies are starting to opt for hot pant’s this season. You can also layer with tights for more coverage! The silver sequins automatically make these shorts more feminine and a gender affirming fashion choice!

Two Piece Lingerie Set

This sexy two piece set is so adorable! Not only that but since it’s a bralette you won’t have to worry about this set creating gapping if you have small boobs like me! The velvet floral details give this a very fall look and I always feel ready to take on the world in a matching set! There are few things I would consider more of a gender affirming fashion choice than a sexy lingerie set!

Gender Affirming Fashion Accessories

Patent Leather Platform Knee High Boots

These platform knee high boots are so beautiful! They will add length to your legs and give you a waif-y model aesthetic. I also the contrasting texture this shoe provides with the rest of your outfit! Anything knee high gives me euphoria which is why these boots are a gender affirming fashion choice!

Gold Headband

This gold turban inspired headband is the perfect detail to add to this outfit! The contrasting metals seemingly go together and give it a high fashion look. Headbands are super feminine and this detail is a gender affirming fashion choice for sure!

Simple Diamond Studs

These simple princess cut diamond earrings are so understated and refine this outfit without having it look over the top. Stud earrings are an essential every girl should have in their jewelry box, especially if you always forget to wear earrings! Earrings are a simple detail anyone can add to their gender affirming fashion look!

Dior Lipgloss

This Dior lip gloss is so soft and pretty! Plus a dior lippy is bound to give you gender euphoria, any lip gloss will do. In this outfit I would maybe do some simple black liner but nothing crazy. Lip gloss makes your lips look super soft and feminine which is why lip gloss is one of my fave gender affirming fashion products.

Black Nail Polish

This black nail polish from OPI is a #1 best seller on Amazon and with good reason. The high shine finish and easy to apply applicator makes this polish an easy choice. Plus you can never go wrong with black nail polish in the fall! Nail polish is an easy way to give you euphoria and is what makes this product a gender affirming fashion choice!

Tarot Cards

These tarot cards are so beautiful! Even those these aren’t a part of your outfit. Tarot cards help me reflect on myself and connect with my spirituality which is important for your well being as well as something innately feminine we posses!

Gender Affirming Fashion: Outfit #5

Baltic Baddie for a Night at the Club

Gender Affirming Fashion Apparel

Vegan Faux Fur Jacket

This faux fur jacket is so extra and definitely makes me think of a cold night out in Moscow! The cropped fit of this jacket will also give you a little bit more curve and show off your a**. Cropped jackets are always a gender affirming fashion choice I gravitate towards!

Maroon Bandage Dress

This maroon bandage dress is such a throwback to 2012 but theres a reason these dresses were a staple ten years ago! they snatch you in and accentuate your curves. This dress might be a better option if you’re post BA but a square neckline would be great if you have small boobs like me! Regardless tiny dresses are a great gender affirming fashion choice!

Tiny Pink Thong

This pink thong is so slutty but this outfit is already pretty trashy so I feel it’s only natural you’d be wearing the skimpiest pair of panties underneath. Super feminine undies are a sexy gender affirming fashion choice!

Platform Cage Stilettos

These platform cage stilettos are also reminiscent of the 2012 club era! Stilettos with a platform can make your feet look smaller and super sexy! Just make sure you have a pedicure with anything open toe! I always feel like a doll when I have heels on which is why stilettos are an amazing gender affirming fashion choice!

Gender Affirming Fashion Accessories

Racks on Racks Clutch

This gaudy clutch is so ridiculous but I feel like it completes the fantasy. Like you’re a russian sugar baby who drives a 6 series bmw from the late 2000’s. This clutch is so campy and serves as a reminder to enjoy yourself when it comes to creating looks. Silly outfit details are always a gender affirming fashion choice!

Diamond Choker

This diamond choker just adds to the tacky opulence we’ve got going on right now. As mentioned before chokers and anything sparkly are both gender affirming fashion choices and this hits two birds with one stone!

Diamond Statement Earrings

These statement diamond earrings match the choker perfectly! I always feel so put together when I wear matching jewelry sets! Again anything sparkly is a gender affirming fashion choice 🙂

MAC Retro Matte Lipstick in Russian Red

This iconic red MAC lipstick in Russian Red is the perfect statement lip for our baltic baddie look! Not only is a classic red lip a gender affirming fashion choice, but a red lippy is timeless!

Switch Blade for Self Defense

This switch blade might live in your purse or perhaps the baltic baddie who owns this piece may keep it strapped to her leg. This isn’t necessarily a gender affirming fashion choice however as women it’s important to make sure we have means to protect ourselves when we’re out at night!

Gender Affirming Fashion: Outfit #6

Cocktail Hour Look Inspired by Madison Montgomery in AHS

Gender Affirming Fashion Apparel

Little Black Dress

This little black dress is a wardrobe staple for all girls! What I like about this one for trans women is the square neckline and flare skirt so you don’t have to tuck if you don’t want to! I would consider this a gender affirming fashion choice because a little black dress is always a safe bet for date night!

Gender Affirming Fashion Accessories

Black Thigh Highs

These black thigh highs are a must for the fall. Not only are they stylish but they’ll keep your legs warm as well! Thigh highs are always a gender affirming choice because how else are you going to stay warm and still wear cute little dresses in the fall!

Simple Black Satin Headband

This simple black headband is an easy way to add a feminine touch to any look. Headbands are always a gender affirming choice because they are such a classy and feminine accessory.

Black on Black Chain Bag

This black chain bag is definitely a Gucci knockoff but I’d actually love to carry this bag! It’s simple and refined and I love the hardware details. This gender affirming fashion accessory is a great way to elevate your wardrobe without breaking the bank!

Black Platform Stiletto Booties

These black stiletto booties definitely remind me of the tumblr 2015 era! And I foresee more styles like these coming back in the near future so this is a great way to stay ahead of the trend. Not only that but paired with the thigh highs it will help elongate your silhouette! Heels are always a gender affirming choice!

Vintage Inspired Stud Earrings

These vintage inspired stud earrings are so feminine, elegant, and they’re pretty inexpensive as well! These earrings add a timeless feel to this outfit I’ve put together. Tiny feminine details are always a gender affirming fashion choice!

Charlotte Tilbury Lip Kit

This Charlotte Tilbury Lip Kit is my saving grace when it comes to picking out my lippy for the day! As someone with fair skin, this shade is my perfect nude. Regardless this set makes your lips look so soft and kissable which is why this is on my list of gender affirming fashion choices!

Matches for Hexing

This box of matches is perfect for lighting your candles in a dark room and performing hexes on boys that do you dirty, though the three fold law states that whatever you put out into the universe comes back three times so be careful. These aren’t a gender affirming fashion choice but I thought they’d be a fun addition to my list 🙂

Gender Affirming Fashion: Outfit #7

Dressed for a Party at Playboy Mansion

Gender Affirming Fashion Apparel

Black Furry Bolero

This black bolero with fur trim is a such a feminine top that will actually keep you warm! The fur trim adds drama to the outfit which I also love! This is a gender affirming fashion choice because the cardigan is cropped, fitted, and you stay warm without losing the sexy factor!

I Love Attention Baby T

This “I <3 Attention” Baby T is so cute and sassy! I thought it added a fun touch to this outfit which is supposed to have bad girl vibe. Baby T’s are always a gender affirming fashion choice especially when they have stupid sayings like this 😉

Plaid Low Rise Mini Skirt

This plaid low rise mini skirt you may recognize from my list of 101 Gender Affirming Products! This bimbo mini skirt is great for a night out.. or a night in 😉 Mini Skirts are always a gender affirming fashion choice because they make me feel like a barbie doll!

Gender Affirming Fashion Accessories

White Knee High Socks

These white knee high socks are the perfect gender affirming fashion accessory to bring the school girl fantasy to life!

Black Peep Toe Stripper Heels

These black stripper heels are so scandalous and I love them for that. Platform stilettos are an empowering gender affirming fashion choice!

Sanrio Plushie Backpack

This Sanrio Plushie Backpack is literally so adorable! Sanrio makes me think about when I was a kid and this gender affirming fashion accessory is a great way to keep this outfit looking playful and cohesive!

Sexy Nerd Glasses

These sexy nerd/secretary glasses are an easy gender affirming fashion accessory to add whether your roleplaying or just want to have fun on your night out!

Red Hair Bows

These red hair bows really do complete the pornstar fantasy! Though bows of any kind are a gender affirming fashion accessory because they automatically feminize your hairstyle!

Too Faced Better than Sex Mascara

The Better than Sex Mascara by Too Faced is one of my makeup bag staples. You get full coverage in just one swipe. I also feature this product on my 101 gender affirming products list. This mascara really gives you those babydoll eyelashes which is why I believe good mascara is a great gender affirming fashion accessory!

Pepper Spray Keychain

This pepper spray keychain for self defense is both super cute and practical. Always make sure to have a self defense tool when you’re out late. There are sick people in the world and trans women can be particularly vulnerable to violence unfortunately.

Gender Affirming Fashion: Outfit #8

A Day-to-Night Outfit Inspired by Taylor Momsen

Gender Affirming Fashion Apparel

Black Mesh Long Sleeve Shirt

This long sleeve mesh shirt is an easy way to add an edgy yet feminine look to your current wardrobe. This is a gender affirming fashion choice because you can wear this top with a super cute bralette which will look super sexy!

Small Grid Black Fishnets

These black fishnets are a great way to step up your hosiery game! The small grid adds some texture to this rockstar’s girlfriend aesthetic outfit! Fishnets are always a gender affirming fashion choice!

Black Low Rise Super Mini Skirt

This super mini black skirt is such a bimbo essential! This form fitting skirt ties together the mesh shirt and fishnets at an affordable cost! This super tight mini is. agender affirming fashion choice because I know I would feel like my sexiest baddest self in this outfit!

Black Thigh Highs

These black thigh highs are a must for the fall. Not only are they stylish but they’ll keep your legs warm as well! Thigh highs are always a gender affirming choice because how else are you going to stay warm and still wear cute little skirts in the fall!

Black Platform Stiletto Boots

These black stiletto boots are so scandalous and a great way to add a heavy metal c*nty vibe to your wardrobe. These boots complete your look and are an easy gender affirming fashion choice.

Studded Goth Speedy Bag

This studded black speedy bag is a great way to add some texture to your look if you are going with an all black aesthetic! Purses are a gender affirming fashion accesory because you can fill them up with all of your girly essentials!

Black Steampunk Sunglasses

These steampunk shades are a great addition to this Taylor Momsen punk/goth aesthetic. Sunglasses always make you look c*nty which is why sunnies are one of my fave gender affirming fashion accesories.

Silver Battle Ax Earrings

These silver battle ax earrings add just a little bit of contrast to this all black outfit! The dangly factor is 10/10 and you are sure to receive compliments in these. Dangly earrings are always a safe gender affirming fashion choice!

MAC Black Gel Liner

This gel liner by MAC is versatile for all of your liner looks! Not only that but you can use this as a primer for a back eyeshadow look. Eyeliner is an easy to tie a look together which is why this liner is a gender affirming fashion staple!

Taser for Self Defense

This Taser for self defense packs a punch to anyone who tries it! CTG’s always should be prepared to fight back against transphobes and creeps.

Conclusion

There you have 8 gender affirming fashion outfits that are sure to turn heads this fall winter! At the very least I hope you can see my thought process when it comes to online shopping as a trans woman. I also hope that this inspires you to have fun and take more fashion risks as you discover your own unique style!