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Wear your military jacket hanging open with a large, oversized scarf on top. The different textures (the canvas jacket against a softer woolen or knit scarf) will add a fun contrast to your outfit. Let the scarf hang down low. Or try tying the scarf in different patterns. Try switching up your military jacket style by pairing it with a thick belt worn at your true waist. This will break up the traditional form of the military jacket and give it a fun new style! Use a belt in a complementary color like hunter green, light brown, or even orange. Try pairing your military jacket with heels or other dress shoes to class it up a bit. Under the military jacket, you can pair dressier shoes with jeans, slacks, or even tights and a cute dress. This is also a fun way to turn your daytime jacket look into a nighttime jacket look. Adding heels (or, for men, nice dress shoes) adds a more formal flare/style. Try carrying a more petite handbag with your military jacket outfit. This will add a nice contrast to the larger size of your bulky military jacket. Try a small handbag with a long chain shoulder strap or a dainty little bowler bag with no over-the-shoulder straps, just handles. Avoid large cross-body bags, as the military jacket is already relatively bulky. Hats are a great way to spice up any outfit. If you want to dress your military jacket down, try wearing a beanie hat for a casual, more relaxed look. If you want to class it up a bit, wear a fedora hat with the outfit. You can even wear a panama hat to add some edgy contrast to the outfit. Try playing on the military tradition a bit by adding your own funky version of military stripes. Add some cute and exciting pins to the breast of your military jacket, or down the sleeve, to give it a little something extra. Add colorful pins that really draw attention to the design.

Summary:
Add an oversized scarf. Add a chunky high-rise belt. Add some dress shoes for a dressier look. Pair it with a dainty handbag or satchel. Throw on a beanie hat for a casual look, or a fedora for a classier look. Add some pins for decorative flare.