By Cindy Weber-Cleary
Updated Sep 01, 2015 @ 3:15 pm
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Late August is always bittersweet. Long, glorious days at the beach, lake, or pool, sunset sails and bike rides, dinner al fresco. All of this seems more precious because you know it’s coming to an end. It’s that back-to-school feeling (even if it has been decades since you graduated!).

It is exciting to shop at this time of year. I’m looking at some leather pieces, chunky knits, a belted coat, a new pair of boots with a solid heel … but, I also have a hankering for something new to wear right now, like the Lemlem skirt above ($275; theline.com). I’m tired of my spring/summer wardrobe and the temperature could stay above 80 degrees for another 6 weeks!

So while I am searching for a few cold-weather updates, I always keep an eye open for some light-weight things that can help me transition into autumn. Cotton and cotton blends make sense. Silk and even tropical wool and thin cashmere can work as long as they are not too fitted. It helps to switch from a sunny summer color palette to something more earthy (vegetable colors such as olive, eggplant, and mushroom) or neutral (navy, charcoal, and khaki) that you can mix later with cozy pieces in October and November.

Unstructured Dresses

Thank goodness for easy, unstructured dresses. Wear them with bare legs and sandals now; later you can layer up with a thin fitted turtleneck worn underneath or a leather jacket worn over. For cooler days, add tights and ankle boots. Here are 3 wear-now, wear-later favorites:

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Shop it: Yohji Yamamoto, $781; matchesfashion.com. Zara, $70; zara.com. Frame Denim, $340; net-a-porter.com.

A-line Skirts

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Flowy or A-line skirts also work well in Indian Summer. These are year-round staples that can be paired with a chunky sweater and boots in cold climates or a T-shirt and wedges in warm ones.

Shop it: S Max Mara, $525; matchesfashion.com. Tomas Maier, $450; farfetch.com. J. Crew, $110; jcrew.com.

Lightweight Jackets

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Should the weather trick you and suddenly turn chilly, try throwing a soft bomber jacket over your shoulders instead of a jean jacket for a slightly sporty-yet-polished vibe.

Shop it: Gap, $70; gap.com. Victoria Victoria Beckham, $710; net-a-porter.com. Ulla Johnson, $390; madewell.com.

Not-So-Basic Pants

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Last but not least, here are a few pant possibilities to keep things interesting as we move forward into fall.

Shop it: (from left) Gap, $70; gap.com. T by Alexander Wang, $456; mytheresa.com. F.R.S. for Restless Sleepers, $505; net-a-porter.com.

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