Okay, back, I still love it but I see Angie made some really great suggestions. This blogger wears exactly those shoes often. You can search for them by name on her blog. She tends to dress very young (age appropriate for her) but is very timely in fashion.
http://thefashionguitar.com/

I have been seeing this kind of look a lot from European blogs where they probably don't have that 80s commuter association because they would never have worn sneakers like that.

I'm not convinced. I think it's a shame as it puts the clothes down.
If you wore it with a pretty pair of black or black patent ballerinas you could totally turn the look around.

Did not read others' comments. My first reaction was that this is by no means a failure outfit. It's pretty okay. I thought it could use more of a punch. Maybe you don't like Cons. But something, either colorwise or a bit edgier. The t-shirt, for me, is most problematic. It's just too much like athletic wear to juxtapose any really interesting element to this. Kind of like, "Yeah, I'm in my sneaks and a workout t, and happen to be wearing a skirt with this."

I honestly think it's only a small change you need to do to make this really sing.

Havent' read all the replies, but my two cents are that the shoes are too geary for this. Sneakers that are more "sassy" would work beautifully. I recently bought a pair of black patent sneakers, which I think would work better... heck, I may even copy you

And fwiw, I like the shirt untucked, sans blazer.

Thank you for all your comments and opinions on this outfit. This has been an interesting experiment and a learning opportunity for me.

I never loved this outfit in the first place, as I all too well realized that something were off from the beginning. I ventured into an area of dressing where I'm much less confident, and I also anticipated your responses to some extent. This is just fine, and I'm comfortable with that! Angie's advice is very reliable and wise, the outfit will definitely work better with Cons, and the bomber, too. I might very well try that soon. My challenge, however, was to find a way to make the Nike Free's stylish. They are hugely popular here, and people wear them with any kind of outfit. I commute, too, and I live near our larges city (which admittedly is very small compared to most cities in mainland Europe or the Americas). But we don't have a "commuter look" established in our society, as most people & workplaces are a lot more casual than what yours are. This was a new concept to me, and interesting.

Scarlet - thanks a lot for the link! You made my day, because it proves that out there, some people are in fact making this shoe stylish, so my mission wasn't entirely impossible, even if I didn't make it. I think your point about it being age appropriate for her is part of the key. It would probably take more to pull this off in my age. If I were 25, I would wear what she wears in a heartbeat. Another 45 years old urban, cool woman could, too, but I'm not her, and Nikes worn as fashion are not coherent enough with my style.

Thank you, all of you, for giving me something to think about, and for making me take another step on my style journey. I won't promise that you never will see the Nikes again, though