First Day of Fall Outfits: What to Wear When the Weather Turns

First Day of Fall Outfits: What to Wear When the Weather Turns

There is always one morning when the air changes and you need a real jacket for the first time in months. This is what I reach for on that first day of fall.

The first cool morning of fall is my favorite day of the year for getting dressed. It is the day you pull out the jacket you have been thinking about since August.

I start with denim, because it is the lightest jacket that still counts as a layer. The TWP Dawson in blue is the roomy, easy one, and the EB Denim Arabella in dark wash is the neat one for wearing over a dress. The Khaite Wyatt in a nude shade is the soft option, and the Dala Mountain jacket in dark green is the one with big pockets and a lot of attitude.

Corduroy and Wool Trousers

Fall pants should feel a little heavier than summer ones. This is the time for texture.

The Christopher Esber corduroy pants in purple are the fun ones, and the Moncler Grenoble corduroy pants in brown have a sporty edge. The Source Unknown Roanna wool-blend pair in black is the easy one to wear with a tee, and the Heirlome tuxedo trousers are the dressier choice for a dinner after work.

Ankle Boots

The first boot of the season always feels like a small event. Pick a pair you will actually reach for more than once a week.

The Isabel Marant Edrik suede boot in brown is the slouchy one, and the Khaite Clive in black leather is the clean one. The Toteme fold-down shearling boot in tan is the cozy pick for a chilly morning, and the Maison Margiela Tabi boot is the one for anyone who likes a split toe.

Scarves

A scarf is the easiest way to make a summer outfit feel like fall. Wrap it once and you are done.

The Max Mara cashmere scarf in tan is the classic, and the Maison Magdalena Ondara in ivory is the soft one for a dark jacket. The Chloé floral-print wool-blend scarf adds a bit of pattern, and the Baobab Austin in black has a fringe that moves when you walk. What I would skip is a scarf so big you cannot find your keys.

Take the First Cool Morning Seriously

One good jacket, a heavier trouser, a boot you love and a scarf. That is all you need to make the first day of fall feel like an occasion.

If this is the kind of week you are dressing for, I would also read my notes on apple picking outfits, cozy girl outfits, long coat outfits and fall brunch outfits.