Fall 2019 Inspiration Board

 Fall 2019 Inspiration: 50s Meets 80s - All image sources linked below Fall 2019 Inspiration: 50s Meets 80s – All image sources linked below

Fall 2019 Inspiration Board

Welp, it’s blazing hot outside, so it must be time to buy long pants and sweaters!

In the South, school starts in early August, so this week often hosts tax free days and back-to-school clothing and supplies sales. Here in Connecticut, I suspect it starts much later since their tax free week is still several weeks away, but there’s still a sense of anticipation – or is that humidity? – in the air that makes you want to try on your clothes, see how much you grew during the summer, and put together a list for what you’ll need in the fall.

I’ve been in packing and unpacking mode for over a month at this point, so my closet has undergone a pretty serious assessment already and the verdict is that I can’t fit anymore clothes in under-bed storage!

But the nice thing about creating an inspiration board before clothes are unpacked and fall magazines release is that I already know what silhouettes, colors, and styles I’m interested in, and can get creative with what I already have, perhaps throwing in a few thrifted finds along the way.

This season, I’m calling my style inspiration “50s Meets 80s,” which is exactly what it sounds like. Heavily influenced by the wardrobes of both The Chilling Adventures of Sabrina and the recent season of Stranger Things, I’m noticing that there’s actually quite a bit of crossover between those decades, and pulling inspiration from both at once lends a kind of balance between the buttoned-up look of the 50s and the eccentricity of the 80s.

Fall 2019 Style Inspiration


Mustard, Teal, True Red, Yellow, Warm Brown, Black, Monochromatic looks


Plaid, Gingham, Stripes, Embroidery


Corduroy, Soft Vintage Denim, Old Leather, Rib Knit, Wool


Straight Leg Pants, Cropped Sweaters, Overalls


Classic Sneakers, Streamlined Boots, Doc Martens

Ideas and Inspiration

If you take a look at my Fall & Winter Style Inspiration board on Pinterest, you’ll see that I’ve had a fairly straightforward set of preferences over the years, give or take color palettes and shoe choices.

But the reality is that I don’t often achieve my sartorial ideals when I start to get really chilly and the days get dark. Since I’ll be walking to class starting in late August, I also have to be mindful of what’s really practical – certain shoes are already out and I’ll likely need to start wearing compression socks to control my Raynaud’s Syndrome.

I’m also fully prepared to confront the inevitable fashion groupthink. What I wore in preppy Charlottesville may feel out of place here (which is actually a good thing, because I was getting pretty sick of feeling like the weirdo for, like, wearing vintage glasses), and I may feel tempted to try something new.

I’m using this time of relative isolation in a new town to try to understand what I choose for myself without so many outside influences. I’ve also been exploring local thrift shops to get a sense of what they have to offer – I have to tell you, I am missing being at the little shop I ran in Charlottesville. So much less visual stimuli!

What I Plan on Buying


  • A fall-toned midi skirt in mid-weight cotton (though I might be able to make do with something already in my closet)
  • A 1950s-style collared wool sweater (already purchased for $5.99)
  • Rib knit mock neck top (already purchased for $3.99)
  • Oversized tee with hand-done details (already purchased for $3.99)
  • A true red or salmon sweater in a natural fiber
  • Lived-in leather lace up boots
  • Classic sneakers (just bought a secondhand pair of these on Poshmark!)

New or Gently Used

Are you shopping much this season? If so, when do you usually start? Also, if you live in the north, what winter gear do you recommend?

Photo Credits (also listed on my Pinterest board) left to right, top to bottom:

One – Skirt // Two – Boots // Three – Closet // Four – Black Monochrome // Five – Camel Monochrome // Six – Overalls // Seven – Converse // Eight – Red Sweater // Nine – Embroidery // Ten – Plaid Pants // Eleven – Vintage Sweater // Twelve – Brown Boots // Thirteen – Red Scarf

pinterest pin that reads Fall '19 wardrobe inspiration - Fall 2019 Inspiration Board

Leah Wise

Leah Wise is the founder of StyleWise Blog. She has been writing, speaking, and consulting on sustainable fashion, the fair trade and secondhand supply chain, and digital marketing for over ten years. An Episcopal priest, Leah holds a B.A. in Religion from Florida State University and an M.Div. from Yale Divinity School. When not working, you can find her looking for treasures at the thrift store.

May we recommend...

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.