Fall Work Outfits for Monday Through Friday

Monday morning has never once felt easy for me, so I stopped trying to be creative and started building a uniform. The pieces change with the season, but the formula stays the same: one sharp layer, one easy bottom, one bag that holds everything.

The sharp layer is the blazer. The Toteme short leather blazer in black is the one that makes jeans look like a decision, and the KALLMEYER Sablier cotton blazer in brown is the softer pick for days with a lot of meetings. The Dries Van Noten draped blazer is the one to wear when you want your coworkers to ask where you got it.

I used to think midi skirts belonged in a movie about the nineties, and now I own two. A midi length feels grown up without feeling stiff, and it makes getting dressed take one decision instead of five.

The Nour Hammour leather midi in black is the sharp one, the Lisa Yang cashmere midi in grey is the comfortable one, and the Proenza Schouler tweed midi in red is what I would wear when I want a Tuesday to feel a little more interesting. Add loafers or kitten heels and a fresh blowout.

Your bag has to hold a laptop, a charger, a book you pretend you will read at lunch and one extra pair of shoes. Everything else is secondary.

The Chloé Spin tote and the Bottega Veneta Andiamo are both structured enough to stand up on their own, which matters more than people admit. The Row Park tote in brown suede is the softer one for a day when you do not have to carry much. What I would skip is anything so slouchy your laptop ends up at the bottom.

A good shirt is the backbone of a work outfit. Tuck it in, leave it out, or wear it open over a tank and it still looks right.

The Lafayette 148 poplin popover is the crisp white one that never needs thinking about, and the Andres Otalora cotton shirt in black is the easy one under a blazer. The Prada tie-neck silk shirt in red is the one to wear when you want a bit more color at your desk.

Pick one blazer, two bottoms, a shirt and a bag, and you have a week of outfits without trying. Everything else is a bonus.

If this is the kind of week you are dressing for, I would also read my notes on fall interview outfits, fall dinner party outfits, weekend errands outfits and long coat outfits.