September is the Best Month for Southern Preps

Wearing a blazer for fall to work.

I love summer: the boating, the hours of daylight in the evening to work out, even the Virginia humidity that makes my hair pouf. But as a Southern prep the best time of year is definitely early fall, when my wardrobe options expand from my button-down and pencil skirt summer uniform to include cozier textures and colors, sweaters and jackets, and layered outfits.

Palette and Texture

A great September outfit

Sometime between September 1st and the autumnal equinox every year I tuck away all my seersucker and Lilly for something more fall-appropriate. No fashion rule bans turquoise and coral, but it doesn’t feel seasonal even if it’s still 90 degrees outside. I save my burgundy sweaters and wool plaid skirts for full-fledged fall in October and November, so in September I wear heavier cotton knits and denim in white and navy (whoever decided white wasn’t allowed after Labor Day clearly had never worn white jeans). I incorporate pops of color with accessories, like the red sneakers above, to keep my outfits interesting.

Sweaters and Jackets

A great preppy shorts and sweater outfit for September

In September I can start wearing my beloved collection of cotton crew-neck sweaters, my denim jacket, and my lightweight blazers. These three items are classics, so it’s easy to find the right cut and color. I look for slightly cropped sweaters, to make my legs look as long as possible without having to tuck the sweater in, which always looks weird. For jackets, I prefer them to be slightly cropped, again, and not too tight through the arms so I can layer a sweater underneath. Now and later on in the season all of these items will be great for layering—peek at any J Crew catalog if you don’t believe me.

Outfits and Layering


Fall layering deserves its own full post, but the beauty of early September is that you have the most possible permutations of outfits since you can still wear shorts or skirts, while bringing in sweaters, jackets, and long pants. I’ve listed a few outfit combinations I love for fall below.

  • A striped sweater, navy shorts, and colorful canvas sneakers. This outfit is perfect for weekend wear, especially if you’re doing a lot of walking.
  • A patterned button down shirt tucked into shorts, loafers, and a sweater. The ultimate “I just hopped off my yacht” outfit, this is versatile and comfortable.
  • A light summer dress with a blazer and pointy flats. The blazer grounds the dress, and the pointy flats give the outfit that adult polish. For happy hour after work, switch the blazer out for a denim jacket.

Do you agree that September is the best month for Southern preps? What are you looking forward to wearing this fall? Let me know in the comments!

3 thoughts on “September is the Best Month for Southern Preps

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