My teenager daughter did this with a neighbor who came out as a trans girl. So I second the advice of finding a friendly teenager to help with this. If you don’t know one, look up the gay student alliance club at the high school your kid will attend, and ask the staff sponsor of that club to recommend a teenager for you to hire for a few hours of shopping. |
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I would suggest looking online for stores that are local and first buy a bunch of sizes for items they would like
Try on at home and figure out what sizes fit best at what stores and then when going to the store it is much easier to shop Old Navy is one place to try for some inexpensive basics |
+1 Those are both companies that specialize in gender neutral clothing, and with styles that minimize appearance of breasts and hips while allowing room for them. They aren't cheap, but you can buy the "tricky" items from those types of shops and then supplement from Value Village and other stores. |
| OP, not sure if this helps, but my DS who has more of a "pear" shape than is typical for many boys, found that the "athletic" cut of men's jeans fit him best. |
| Find a good tailor |
| Maybe worth calling a LGBT+ community outreach program or nonprofit and ask if they have any volunteers who could help. |
| I have a couple of the Wildfang short sleeved button ups - they’re really well made and comfortable for those of us who like to present in a more androgynous or masc way. |
| My teen daughter often likes to dress in a more androgynous way. She has found some shirts she really likes in the men’s section of the j crew outlet store. I think the j crew men’s stuff runs smaller and is just cut in a way that works better for female-born bodies. There’s one on Rockville pike and they have a dressing room. I also have a teen niece that dresses fairly androgynously and she gets her jeans from the men’s section at carhart — they looked great and are apparently very trendy in the NE. She said teens of all genders are wearing their work shirts too. |
| Uniqlo is a good option, OP. |
| Any adult is likely to get this wrong. I would look into hiring an older teen to take him shopping and give him advice on what fits. |
| I don’t know of a place like that, but that would be an amazing service! |
I second J Crew Factory as a source of men's clothing that seems to fit female-born bodies well. They have a website, too. |