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

Cutouts are your friend.

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.

Cutouts are your friend. Noted.

I'll be wearing this perfectly constructed dress on summer nights and fall days.

A blazer is at the top of my list of splurge-worthy items.

She's perfect.

Trading tees for knits is a great start to dressing for cooler weather.

This top looks designer.

Your sneakers can transition, too.

It's the simple tie for me.

Invest in your basics, and then style them up with fun colors.

Did someone say wedding guest?

I'll be wearing these as long as open-toe sandals are socially acceptable.

I'm loving this colorway.

There's a reason these pants always sell out.

Okay, cute.

This is what happens when corset detailing is taken to the next level.

This top is perfection.

It's time to start sweater shopping.

Sophisticated tops will look great under that leather jacket of yours.

An immediate add to cart.

Love a leather mini.

Oversize bomber jackets will rule the streets.

We love her.

Asymmetry for the win.

One glimpse at these, and suddenly, I'm a sneaker girl.

You can wear them more ways than one.


Someone invite me to a pumpkin patch.

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.

Everyone needs this.

It's a cardi party.

I'm so here for this.

Every button is perfection.

Did someone say pockets?

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