Riding Boots. Preferably in cognac or some grey tone. Mmm, so wonderful and comfy.
Oxfords: cute, gender bending. Buy them in leather, canvas, or suede...just get a pair. Any color, nuetral or bright will do. For shorter legs, I suggest buying a pair with a built in heel or wedge. Wedge oxfords are my favorite
Flirty Maryjanes. Update your closet. Softly pointed toes and a nod to the 40s are all around us. Engage your desire to play dress-ups.
Army influenced desert boots. A tip: wear them with short, tights and thin scrunch-able socks to show off the boot as a main accessory...a perfect way to transition from summer wardrobe to fall.
Images: Top Center Tall Color Block BDG Boot, Center Right 80%20 Oxfords, Center Left Minna Parikka Heart Maryjane, Bottom Center Clarks Desert Mali Distressed Suede Boot