You really just can’t beat September in New York (or Montauk, as the case may be). The weather is to die for and the wardrobe options are endless. I’m so happy to be pulling out sweaters and boots from the back of my closet! I thought I’d share a few of my favorite fall layering tips for those of you equally excited for cooler climes.

pink old navy sweater fall layering tips

1. Start with a button-down shirt. Roll the sleeves and decide whether to pop the collar or wear it down. This one from Old Navy is actually a popover which is nice because, without buttons all the way down the front, it lays a little more flat underneath a sweater.

michael kors double strap watch

2. Next add a blazer or a sweater, rolling the sleeves so that you can see the button-down underneath. If you’re wearing a sweater over your button-down, you can always add a blazer on top, but most blazers aren’t cut to house bulky layers underneath.montauk yacht club

3. If you’re going for a more casual look, a t-shirt and a cardigan are an easy pairing. Add a belt as your finishing touch.

old navy shirt converse sneakers

4. Always the proportions of an outfit. If you’re wearing two or three layers on top, you probably don’t want to wear bootcut denim or drapey dress pants on bottom. Stick to skinny jeans, cigarette pants, dark leggings, or a skirt and tights.

5. Consider a third layer on top, whether it’s a light jacket or a chunky scarf. It’s all about the details!

fall layering tips

Chanel “Extatique” lipstick  //  Old Navy sweater ℅  //  Old Navy oxford pullover shirt ℅  //  Michael Kors double leather strap watch  //  Rag & Bone skinny stretch Kensington jeans  //  Converse Chuck Taylor sneakers

This post was sponsored by Old Navy. Check out Old Navy‘s latest fashion lineup in store or online at oldnavy.com.


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  1. Old navy is my go to for affordable pieces to mix in the wardrobe. They are on trend for this fall. In addition to this great oxford, their quilted ballet flats with patent cap toe, snake skin clutch, and bucket bag are in my rotation. And who can resist the neon pink ballets as well.

  2. Love this! Now only if I could think of wearing sweaters soon! It is still in the mid 90’s here in the desert. You can bet the second a cool breeze blows through here, I ‘ll be pulling out my sweaters!


  3. Loving this outfit! Perfect for the transition into fall! It gives the cooler weather a pop of color! 🙂

    Sophia B.