I'm Shopping for 2 Seasons at Once—35 Pieces I'll Wear From Summer to Fall

One of my favorite times of the year is always when we're getting ready to embark on a new chapter. Transitioning from summer to fall is my specialty because I love buying evergreen pieces and finding new ways to style my summer pieces. I live in New York City, so I'm sure you can imagine how much storage space I have. Before every summer begins, I send all of my winter things to my parents' basement for safekeeping. So when things start to cool down, I tend to get creative with my summer wardrobe until I have a chance to go home and collect my baggage. I fear the day that I'll need to shove all of my clothes into my own closet, but we'll worry about that problem when it arrives.
So now more than ever, it's important to start buying pieces I can wear for several months to come. Below, you'll find 35 items that I think will effortlessly help me transition from season to season.
A blazer is at the top of my list of splurge-worthy items.
Trading tees for knits is a great start to dressing for cooler weather.
I'll be wearing these as long as open-toe sandals are socially acceptable.
Oversize bomber jackets will rule the streets.
One glimpse at these, and suddenly, I'm a sneaker girl.
A good gemstone is a great way to start a new season.
Is it too soon for snow boots? I'd wear them now in the house and later outside.
Don't get me started on how many ways I'll be wearing this dress.
Next Up: I Won't Stop Shopping for Summer—Look at the 33 New Things in My Cart
Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.
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