The mistake is treating a bomber like a jacket that goes with everything just because it goes with jeans. It doesn't. The boxy shape and the ribbed hem and cuffs make it a very specific silhouette, and once you see it as blocky rather than neutral, you start putting it with the right things instead of just the easy ones.
Where it falls short is anything that already has volume or structure. A full skirt, wide trousers, a dress with any sort of shape to it, the bomber sits on top like an afterthought and the whole outfit loses its line. It's also not the one for smart occasions where you need a jacket that closes properly and sits flat, because bombers are built to be worn open or zipped to the chest, not buttoned up like a blazer. If you need something for a wedding or an interview, this isn't it, and no amount of styling fixes that.
Fit is where most people go wrong buying one. You want it close through the shoulder and body, because the ribbing at the hem is doing a job, pulling everything in, and if the body is too big that ribbing just sits there bunching like a sad little frill. The sleeves are the other place to check, they should hit right at the wristbone or just above, because bomber sleeves run looser than most jackets and a long sleeve will swamp your hand every time you reach for something. Try lifting your arms fully above your head in the shop. If the hem rides up past your waistband and stays there, size up.
Before you buy, check the zip pull is metal and substantial, not the thin plastic ones that snap within a season, and run it up and down twice because a sticky zip on a bomber is a daily irritation, not a one off. Check the lining too, a lot of cheaper ones have a slippery polyester lining that catches on jumpers underneath, so if you mostly wear it over knitwear, look for something softer. And press the ribbing at the cuffs between your fingers. If it's gone slack when the jacket's brand new on the rail, it'll be gone for good after a few wears.
It doesn't sit well with anything already cropped underneath, because you end up with a gap of midriff you didn't plan for, and it clashes with other sporty pieces worn at the same time, a bomber plus joggers plus trainers reads as one note rather than an outfit. Pair it down with something that has a bit more shape instead and let the jacket be the blocky bit.
Wash it inside out on a cool cycle if the label allows, it keeps the ribbing from stretching out of shape in the drum.
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