Fall Date Night Outfits That Look Like You Did Not Try

Fall Date Night Outfits That Look Like You Did Not Try

There are nights when I want to look like I threw something on, and I definitely did not. This is the black dress, boots, earrings and leather jacket combination I keep coming back to.

Some nights the goal is to look like you barely tried, while having definitely tried. I have a pretty reliable formula for it, and it starts with a black dress.

Everyone needs a good one, and fall is when I like mine with sleeves or a bit of structure. The Toteme slouch waist crepe midi scarf dress is simple in the best way, while the Christopher Esber concave wired dress is the one for when you want a little drama. The Co shift dress is the one to pair with everything else on this list.

Boots That Can Handle the Walk

Date night in October usually means a walk between the restaurant and the bar, so I pick boots I can actually move in. Nobody has fun in shoes they are counting down to take off.

The Neous Ran underknee boots in suede look great under a short dress, and the Khaite Ona ankle boot is the one that keeps things sleek. If your dress is simple, The Row Hike boot gives the outfit an interesting edge, and the Miu Miu buckled boot is the one with some attitude.

Statement Earrings

Skip the necklace and let one pair of earrings do all of the talking. Pull your hair back and the earrings become the whole outfit.

The AGMES Long Tess earrings with onyx are the sculptural pick, the Toteme gold rope drops are the easy one, and the CANO Sami Muhu pair is the loudest of the group. What I would skip is wearing statement earrings and a statement necklace at the same time.

Leather Jackets

The leather jacket is what keeps a dress from looking too precious. Throw one over your shoulders and suddenly the outfit has a point of view.

The Balenciaga biker is the classic black one, the Altuzarra Fenice jacket is the sleek one, and the SLOAN oversized bomber in brown is the softer take. Keep the jacket slightly roomy and let the dress show underneath.

Wear It Like You Forgot About It

A simple dress, a boot you can walk in, one loud earring and a jacket you do not mind getting wrinkled. That is how you look relaxed without admitting you planned it.

If this is the kind of week you are dressing for, I would also read my notes on fall concert outfits, fall dinner party outfits, fall brunch outfits and fall wedding guest outfits.