Preppy Layering for Fall

Preppy holiday outfit

After I wrote about why September is the best month for Southern preps, I started thinking about the sartorial options that come with chilly fall weather. I can wear collared shirts with sweaters in September, but the real layering doesn’t start until October. I plan to layer up on cozy sweaters and blazers until I need a real coat in December.

The Building Blocks of a Preppy Fall Layering Wardrobe

  • Patterned button-down shirts in flattering colors – Button-downs and textured pencil skirts are the backbone of my work wardrobe. I prefer patterned button-downs because only the collar and cuffs are visible underneath a sweater or jacket, so the pattern accents the outfit without being overwhelming. If you shed the other layers, the patterned shirt still adds some oomph. My shirts are white, pink, and blue, but any versatile color will work. Be sure to choose shirts in a color that’s flattering to your skin tone since the shirt is closest to your face.
  • Sweaters – These should be fitted, but not so tight that you can’t wear a button-down comfortably underneath. I have a few wool sweaters, which I can only wear over collared shirts because they’re so itchy, but most of my sweaters are cotton. I like to have a few sweaters in fall-specific colors, like burgundy and camel, along with the navy, white, and pink sweaters I wear all year.
  • Skirts – I prefer flared skirts for layering, since a pencil skirt can look dowdy if you wear it with too many layers. Like with sweaters, I have some bold fall skirts in plaid and mustard yellow and some plain year-round skirts. You can experiment with skirts in colors you wouldn’t normally wear, since the color is far from your face.
  • Jackets – I’ve spent a lot of time scheming up ways to wear the ridiculous blazers I accumulated my junior year of college under the delusion that I would wear them to work. Since I didn’t get a job at a Scottish hunting lodge, I haven’t been able to wear any of them as much as I’d like. I’m glad that I had the restraint not to buy matching skirts for any of them, since a corduroy skirt suit for work is more than I could pull off.

Putting it all together

I planned all of these outfits with the same principles—I embraced layering and fall hues, but chose complementary colors and kept the combinations from getting too busy.

September Transition Casual Friday

September transition outfit

When you’re in the fall layering spirit but it’s still September, try this comfortable layered outfit. I paired two preppy summer staples, white jeans and a pink gingham button-down, with a navy cotton sweater. Sperries keep this outfit work-appropriate without feeling stuffy.

Back To School for Adults

Layered back to school preppy outfit

It’s been years since my last first day of school, but September and October still make me want to watch movies with good back-to-school fashion like Heathers, Clueless, and Can’t Buy Me Love. If you’re hankering for back to school fashion or re-watching Gossip Girl for the fourth time and have school uniforms on the brain, wear a flared navy skirt, like this J Crew skirt that every girl I know owns, with a blue gingham button-down, pink cable-knit sweater, a corduroy jacket, and loafers to nail that preppy back-to-school vibe.

Menswear for Work

Preppy layered menswear outfit

With a more neutral palette than the last two outfits, and slacks instead of a skirt, this outfit is more Annie Hall than Lilly Pulitzer. Any day that you want to feel sharp rather than girly, put on a blue-and-white striped collared shirt with slim-cut, slightly cropped navy slacks. Layer a loose-fit burgundy sweater and a gray herringbone blazer over the shirt, and finish the outfit with neutral heels to keep the outfit from feeling like a costume.

Fall Colors

Preppy layered fall look

This outfit includes two bold pieces, a wool plaid blazer and a mustard skirt. These two fall items pair well because of the shared autumnal palette of the gold skirt and the yellow stripe of the blazer. I kept the rest of the outfit simple with a plain light blue button-down and a pair of pink pointy-toe flats to keep the gold buttons on the skirt and the elbow patches on the blazer from being overwhelming.

Holiday Cheer

Preppy holiday outfit

This outfit is perfect for a casual Thanksgiving get-together with family or friends. I paired the star of the outfit, a red plaid skirt, with a denim shirt and camel sweater. Silver flats are festive but comfortable for a long, relaxed party.

Have you started layering for fall yet? Would you wear any of these outfits? Let me know in the comments!

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