The major issue with this transition period is that everyone is dying to crawl into their oversized sweaters and booties, but they also don't want to accept defeat and the reality that summer is over.
To compromise, I always pair dresses and oversized sweaters with boots for a fall look that allows for comfort in all temperatures and weather conditions. Focusing on neutral colors and fall tones will help drag the look into fall, while colorful accessories and summer patterns and textiles allow a shred of summer to remain in your outfits.
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