Yesterday, I walked outside and felt the unmistakable chill of fall.  It was not a welcome sensation.  After a very long winter, I am not prepared for an early fall.  But even if I’m not emotionally ready, my wardrobe needs to be.

Last fall, I bought a handful of pieces that I can’t recommend highly enough.  These items were the foundation of my wardrobe — the kind of items that you wear too much.

I now own this Free People Ottoman Sweater in four colors (fig, green, black, and ivory).  It’s perfect with jeans or leggings, the ideal combination of slouchy and structured.  I can’t recommend it enough.  Just one word on sizing — the sweater is so oversized anyone size 8 or under will likely want an XS.

This Maggy London dress was in constant rotation when I worked the legislative session last winter.  I wore it under long coats, with crewneck cardigans, and under moto jackets.  It is so comfortable and easy, but looks professional and put together.

Nordstrom Rack has it on sale for under-$50, but they don’t have all the sizes.

This sweatshirt from Daily Ritual is the piece I reach for when I travel, when I’m watching my friends’ kids play sports, and anytime I need to look pulled together while running errands.  It’s a good mid-weight, and so soft.

Last fall, I went to NYC for a trip and just packed wrong.  I had an informational interview and the outfit was WAY too professional.  So where did I go?  J.Crew.

I picked up this Regent Blazer in camel to wear with a simple black sheath and pumps, and the outfit was the perfect mix of “I’m a professional” and not trying too hard.  But once I got home, I ended up wearing it with everything.  T-shirt and jeans, camel blazer.  Cocktail dress for drinks with friends, camel blazer jauntily perched on my shoulders.  Over pajamas for a 5:00AM Starbucks run, camel blazer.

If you want something even more casual, their Sophie Open Front Sweater-Blazer is nice. Just be aware it pills, a lot.  So you’ll need a sweater shaver.

Have you ever heard the phrase “they go with nothing, so they go with everything?”  That’s these leopard point Rothy’s.  The color palette is off, being all brown, but it honestly doesn’t matter a bit.  I wore these constantly.  I wore them around my office between meetings.  I wore them to the grocery store.  I even wore them to a wedding.  (Don’t judge the groom was wearing jeans.)

The lesson here is that leopard flats are a must, but Rothy’s are much easier than calf-hair.

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