How To Pick Clothes If You’re Transgender Or Crossdressing

  1. Don’t Choose Flashy Clothes For Your First Outfit
  2. What Kind Of Neckline Should I Go For?
  3. How To Pick Clothes That Hide Your Muscles
    1. Clothes Recommendations (Tops)
  4. How To Pick Your First Dress (Or Skirt)
    1. Dress And Skirt Recommendations
  5. Finding Outfit Ideas

Don’t Choose Flashy Clothes For Your First Outfit

Picking clothes when you’re transgender or just dressing feminine isn’t so simple. You might be thinking, “get the sexiest looking red dress I can find”, right? For someone who’s just beginning their transformation journey, this is the worst choice possible because it will draw a lot of attention to you, and bring eyes to your chest. If you don’t have any breasts yet, that’s something you’ll want to avoid.

Your first outfit should be something you’d see any woman wearing on a normal day out. Think something like a simple blouse or sweater, and some jeans. It’s much easier to blend in that way, and you can still do things to feel sexy in an outfit like that.

What Kind Of Neckline Should I Go For?

To all the transgender women and crossdressers out there, I recommend avoiding any necklines that’re designed to show off cleavage until you have some. I typically stick to boatneck, round, and high neck necklines when I want to go for an everyday type look. For something sexier, I go for off shoulder or asymmetric/one shoulder necklines. Shoulders can be just as sexy as breasts!

How To Pick Clothes That Hide Your Muscles

While there are great looking women who are bodybuilders, they have a lot less muscle mass than a male bodybuilder would have. If you’re someone who lifts weights regularly, I strongly recommend putting together outfits that minimize the perception of the size of your arms.

This means for tops, I strongly recommend wearing something with long sleeves when the weather allows for it. It’s alright if the sleeves are skin tight, but it’s best if you find some that are loose and flowy instead. I still do bicep curls regularly and none of my photos show a hint of it. (Make sure to add me on FetLife if you want to see what I mean.)

Muscle mass in the legs, however, is totally fine. Skirts and dresses typically don’t go high enough above the knee to show enough of your thighs to cause any damage in perception. Not to mention, genetic women can also build pretty bulky legs.

Clothes Recommendations (Tops)

Clothes like this top are great for hiding your muscles

This top is an off shoulder neckline top. It shows no cleavage, looking sexy by showing plenty of skin elsewhere.

How To Pick Your First Dress (Or Skirt)

For skirts and dresses, make sure you get an “A-Line” fit one. What this means is that it widens and flares out at the bottom and creates the visual of a triangle toward the lower end of your body. My reasoning for this is that people assigned male at birth typically have bodies shaped like a straight line, or widen at the top. So a dress or skirt like that would help create the impression of an hourglass figure. Wikipedia probably talks about it better than I do.

Dress And Skirt Recommendations

Clothes like this dress make for great outfits

This dress was actually the first one I bought, and I still have it. It looks good on anyone without effort.

This skirt is a perfect example of an A-Line fit.

Finding Outfit Ideas

You can get outfit ideas by searching google for terms like “cute summer outfit” or “sexy summer outfit”. You could also enter search terms that include the color of your wig, like “hot outfit for brunettes”. Basically something that matches “[ADJECTIVE] [SEASON] outfit” will work, as there are tons of websites and articles on Pinterest dedicated to this.

There’s also a great feature on Amazon’s phone app called “StyleSnap” where you can upload a picture of someone and it will find clothes on Amazon that look similar. You can get to this feature by clicking the camera shaped button in the search bar. That feature is also on the desktop site. You could also try Prime Wardrobe, which lets you send clothes back without a hassle if they don’t fit. I can’t remember the amount of times I’ve bought some womens’ clothes and they turned out not to fit right.