Here are 18 of this season's best baseball and bomber jackets. From plaid to neon and versatile to niche, this a carefully curated selection of jackets that have plenty of character. So, how should you style the bomber or baseball jacket? Almost anything goes! I would personally wear a bomber with flat boots, heeled booties, pointed pumps, or wedge sneaks. Go for an edgy look and wear the bomber jacket with an above-the-knee pleated dress.