Great shoes for fall

To me, loafers always felt preppy (or reminded me of Thriller-era Michael Jackson). But for our most recent hair tutorials, my friend Caroline wore patent black loafers with everything from jeans to dresses, and she looked effortlessly cool and tomboyish. This cute pair also comes in oxblood. I'd love to wear them every day this fall, wouldn't you?
P.S. Parisian wedges.

(Photos of Caroline by Jamie Beck for Cup of Jo. Jeans are vintage Levis; baseball tee from J.Crew; green men's jacket from Nicholas K, and striped dress from Madewell)

Fall trend: Navy nails

This fall, I've been spotting beautiful women all around the city with navy nails, which look incredibly chic and elegant. Here, my friend Kendra is wearing this polish (Midnight Cami). Thoughts? Will you wear navy nails this fall?

(Photos by Alpha Smoot for Cup of Jo; styling by Kendra Smoot. Army jacket from Urban Outfitters, similar chambray shirts here and here, and pouch from American Apparel)

Fall trend: Dark red lipstick

I usually wear bright red lipstick, but this fall, lips are going dark. Yesterday Toby and I walked over to the NARS store and found the prettiest color: Terre de Feu. Afterward, I felt really sexy, even in jeans and a T-shirt and with a baby on my hip.

The trick is to apply the lipstick, and then kiss it off on a tissue, so it's more of a stain; and then reapply a top coat. That way, it stays on for ages (and won't rub off if you have drinks or dinner).

Will you be wearing dark red lipstick this fall?

P.S. Dark red nails, and fall wedges...

(Photo by Stockholm Street Style)

Fall Do or Don't: Denim on denim

Denim on denim is having a moment. I keep spotting beautiful women pairing denim shirts with jeans, and they look incredibly chic. Who would have thought?! The trick seems to be wearing the softest chambray shirt you can find, which makes the look feel effortless (versus stiff).

Thoughts? Would you wear this?

P.S. Jordan suggests adding red shoes, which is a cute idea!

(Photos from Stockholm Street Style and The Sartorialist)