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Ashley Lynn, Lee or Jo would be too unisex and in today's world (at least in America) way too feminine for the general population's liking.

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I, however, do like seeing original boy name-switched to female names on males. If your son didn't like it, he could choose to go by Ash (which could be short for a number of masculine names) or his more masculine middle name.

I have a male cousin named Ashley James (it's more popular for boys in the UK). I think if you live in North America then you probably would need to use a masculine middle name. Not 'super macho', but not androgynous.

The middle name doesn't have to be "super macho". Instead, go for a name that is definitely masculine and unlikely to be used on girls.

It would certainly help to have a super macho middle name. Please don't name your son Ashley Lynn, Ashley Lee, or Ashley Jo! My advice would be to forgo Ashley for a boy altogether. It may still be technically a male name, and at one time I imagine it was usable for a boy, but given how wildly popular it became for girls, I don't think it is now.

Here in England Ashley is much more common for a boy than in America, but I still think that it needs not a "macho" middle name, but a clearly male name in the middle to balance it out. Something like Ashley Sebastian or Ashley Alexander.

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Even though you didn't ask for opinions on the name; I like it. I much prefer it on a boy than a girl, but I love the nickname Ash - I'd be more likely to use Asher to get to that though.

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I would go with something a little less unisex than the names listed. I do like Ashley on a boy though.

I LOVE Ashley on a boy, I know a young boy named Ashley but he's in England. Name your child whatever you want and people will accept it as long as you tell them that it's Ashley with confidence.

I would say yes, because it's likely he'll use that as his name when he gets older. You can certainly name your child whatever you wish, and I'm not intending disrespect, but if you live in North America, I would advise you to consider using another similar name like Asher, Ashton, or just Ash instead, which are still fresh and modern boys names. Ashley is a nice name, but it is really mostly to only used for girls these days (in the aforementioned geography at least).

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Good luck making your decision!

Put yourself in your son Ashley's place.
The answer is yes, you do need a mascuinline middle name for Ashley, if you use it for a boy at all.

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The one male Ashley I ever know, a few years older than me, none of us knew his name was Ashley till graduation time, because he always went by his middle name, which was Matthew. We only knew him as Matt. People who knew him since kindergarten said he was always called Matt, including by his parents. And there were very few female Ashleys his age.

I would balance it with something more masculine for sure. You don't have to but I would.

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Also Jo is really feminine as a middle name, especially that spelling.

You can do as you please ... don't you think so?
If you're anxious about it, that probably means you have some reason to feel a little uncomfortable about naming a boy Ashley Lynn. Listen to your heart about it. Are you giving him the name you'd want to have if you were born as a boy this year? It's okay.

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I personally don't think middle names matter. People can almost always keep their middle names concealed if they wish to.

I would pair it with something more traditionally masculine, but that's just me. I would advise against Ashley Lee, because it just sounds bad.

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It wouldn't be the end of the world if you named him something like Ashley Lynn, though. People might make comments, but they would get over it. I remember a male singer named Ashley Angel when I was growing up...I think he was in O-Town? I don't remember, but he was obviously a guy, and girls really seemed to like him. It's fine.