Most of the time, not a big deal and not cringe for all of these items in this poll. Funny when noticed, but that's usually it.
How dare you put Fred Gall as a poll option! He's the antithesis to cringe.
When filming clips for a video or a proper edit: it's awkward if obvious.
The exception is when it's egregious there'a a mismatch and it looks really out of place. This is common with sport brands and less with skate brands, tbh. Examples:
Nike blazers with the Adidas track pants. That looks weird.
Emerica hoodie with etnies shoes doesn't look that weird.
Lakai t shirt with Huf shoes.
Thunder windbreaker whole skating Ace or Indy trucks. Not that weird but truck loyalists may give you shit for it
Skating is one of the few activities where you can skate one brand and wear a different one for clothing and it's accepted for the most part. Most aren't sponsored so there's no urgency or pressure to match branding on apparel with gear every single session. The same is not seen as often in other sports where people grill you more on running Adidas bball shoes with Nike shorts and Nike socks.