There have been many great replies already but I wanted to share my Thrift Store Journey in case it helps.

My first issue was simply getting up the courage to start the process of creating my new wardrobe. I had already donated a bunch of my old clothes to make room in my drawers, and took everything else out and organized them in a more thoughtful way. Now I have a drawer dedicated to my skirts and pants, and one for my shirts/blouses etc. Also made room in closets to hang dresses and such.

My first clothes shopping experience was with target, and I went with the idea that I was just looking for 1 thing to try so I could figure out sizing better. I ended up with a pair of high waisted stretch pants and then bought a second pair from them online. My experience at Target was OK, I even asked an associate about the size and checked on how the changing rooms worked and there wasn’t any problems. But I was SUPER nervous the whole time.

A couple months later I finally worked up enough confidence to try the thrift store near me. I have now visited it a total of 5 times. I tried to go just after they opened and I spent about 3 hours each time. Here’s what my (approximately) $300 got me so far:

• 15 shirts
• 9 skirts/skorts
• 9 tank tops for layering
• 5 casual pants
• 3 dresses
• 2 pajama bottoms
• 1 sleep shorts

The dresses were the most frustrating thing to buy. Sizing is TERRIBLE and I had to try on probably 30 or 40 dresses (no lie) to find the 3 I eventually got. Some of the dresses I went really large on size and they still didn’t fit. I think I got super lucky to even find 3. They were also more expensive than the other clothes. Generally everything else was $4 to $6 but the dresses were more like $7 and up. The most expensive was around $12.

Each time was very hit or miss. First time I got super lucky and pulled in several shirts, blouses and skirts.
The second time I had way too many things that I really really wanted but just barely didn’t fit. However, I did pick up a skirt I’d found the first time, but at the time couldn’t figure out how to get into it lol. It has a tiny hook and a little zipper that is hidden. Really cute but I was afraid of breaking it the first time because I couldn’t see the zipper so I put it back. One of the other 5 visits was also very good. By the 5th time I was much more relaxed and focused. They had 5 changing rooms, so sometimes I had to wait a little while.

The other thing that really helped is I started keeping notes on what I liked and what I wanted to try and get the next time I went. Also, when I got home each time I laid out everything on my bed and cut the tags off and took pictures so that I could remember what I got. At this point I have a solid core going, but I still need some warmer clothes to wear in the fall/winter so I’m sure I’ll be going back there eventually.

This may have already been mentioned but one thing that I started being very careful about is looking at every seam and checking for threads coming loose. One of the neat shirts I got ended up having a small tear at the collar so I don’t really want to wear it until I can learn how to sew that together. Once I made that mistake I was alot more careful when shopping.

The other thing I noticed is that spending that many hours peeling through the racks with all the different metal hangers was absolute hell on my hands and especially my nails. Almost every time I went I had to trim my nails because I’d nicked them so much.

I started keeping a mental list of the “cheap” clothing like Shein etc and tried to stay away from that stuff. I found some website that had like 40 different cheap brands listed, what they called “fast fashion” and made every effort to shy away from those wherever possible.

Overall it was a great experience and I have discovered that I really enjoy shopping now. I also really love trying to figure out what I’m going to wear in the morning. Sometimes I have a vision the night before and set my clothes out for the next day. I tried to get some things that have some similar colors and some things that were just mono color and that has been really smart. Several items go with several other items so I try to wear what suits my mood and the weather.

That’s all I can think of for now. I wish you the best of luck and hopefully you have a decent thrift store near you!

Ive had incredible luck thrifting. I usually go once every 2 weeks and only take items I really like. Early on I stuck to sports bras cause theyre more forgiving as you grow, so they last a bit longer.

A line silhouettes tend to look good when your hips aren’t super wide, as your fat moves around tho your hips will fill out. More than anything have fun with it. Try new clothes outside your comfort zone. Get lots of accessories too!! Putting together an outfit with accessories is so much fun. Gives you the opportunity to further express yourself 😊

If you don’t know what you like yet, or what your style is, try going on FB marketplace or Craigslist and look for a closet clean out. This is the season for yard sales too. Try to find someone listing things in roughly your size (they sometimes will say “lots of XL clothes!” ) and then you can pick up giant bags or whole bins of random clothes for not even 10 dollars.

If you score a haul or two like that and get a chance to play dress up and experiment, you can figure out what you like on your body. What kind of necklines do you feel are flattering, what silhouettes, what length skirts or sleeves etc. Once you have a better idea of what you actually like on you, you can move on to shopping at thrift stores. There, you can keep an eye out for pieces that fit the profile of clothing you decided you liked. Not all thrift stores let you try on clothes and you might not feel confident enough to throw it on over what you’re wearing, so be prepared to buy, try, and maybe return.

Try to go for higher quality items made of natural materials. You should aim for as little polyester, nylon, acrylic or spandex as possible. Feel the clothes and see if they have weight to the fabric, and structure to them. Good quality clothing has construction and patterning that makes them fit a body better than just a sack or a rectangle. Look for clothes with linings and complexity.

Hopefully you will be able to build a starter wardrobe of some good core pieces rgat you love!

I’m taking this same journey right now as well. I was in a similar situation as you (mostly plain shirts and hiking pants, think “Eddie Bauer”). I also really want to branch out to more interesting styles. The one thing I’ve learned from my partner is that layering is pretty much essential unless it’s a scorching hot day. You can also seriously consider the same sources for your current clothing (Eddie Bauer’s Women’s section is not half bad for comfortable things that fit well, if a bit boring). You should consider that bottoms are possibly going to be tighter in some areas and looser in others unless or until hormones or surgery happen. I have a wide and sturdy ribcage, so tops all feel like they’re too tight, especially at the armpits. Sizing up is an option, but so are looser cuts and stretchy materials. I find that I like a tighter base top and something loose to go over it like a hoodie, wrap, or shrug.

Experimentation is the only way to really learn anything. You can always try to abuse the Amazon “try 5 things out” nonsense, or find a shop that’s trans-affirming or go to the next city over if you’re shy and just try on everything until you find what you like. I have known people, especially my mother, to spend an entire day trying on clothing and buy one or two items. Or a dozen! I actually find the shopping and discovery part of this to be fun and a little relaxing. Think of it less as a chore or a scary task and more like a way to explore yourself and your identity, then make a fun day out of it!

I am on the same journey! Let me share my tips.

1. Thrifting / second-hand clothes are a great starting point. It allows you to dip your toes into femme clothes shopping without blowing a hole in your budget.

2. Shop with a close friend. I personally have a cis female helping me out when I shop in person for femme clothes. Getting real-time feedback helps soooo much!

3. Be cautious about size options from online retailers. A Large shirt from company X may be different than a Large shirt from company Z. This is a known “feature” of femme clothing.

Dont worry too much about a specific style. Find clothes that resonate and make you happy and confident.

Buy a little at a time, and nothing remotely expensive, especially if you plan on losing weight. Amazon is your friend here.

Look on pinterest and in real life for women wearing things you like. Then copy them! It’s that easy, but it takes a while to find your own style. You’ll have plenty of time as your body changes to explore.

Have fun!