Read to the end to find top preppy styles for this fall

Good morning and welcome to this edition of The Weekly Preppy! You may not have noticed, but it’s preppy season (aka, fall). Some say the summer is the season for preppies, but here at The Weekly Preppy we firmly believe the crisp air of October is where a preppy thrives most. That’s why we’re kicking off the season with our top preppy styles for autumn! By now we hope your coffee is brewed, so find the comfiest seat in your house and settle in for the next few minutes.

The Weekly Preppy’s top finds & deals for preppy clothing and accessories this week

5. Canvas Work Shirt

Nothing says “work hard play hard” like the timeless canvas work shirt. Breathable enough to handle a hike on a sunny, 60° New Hampshire afternoon, but warm enough to keep the chill away on October mornings. Bonus points if you find one that fits just big enough that you can throw it on over a cable knit sweater!

Our favorite comes from L.L. Bean, but you can certainly find great options from Land’s End, Orvis, Barbour, or your favorite outdoor prep brands.

4. Corduroy Hats

Call it a comeback if you want, we say it never left. Corduroy is the fabric of the season for preppies, and there’s almost no way you can go wrong. The corduroy hat is an excellent way to keep your head warm without pinching your ears (and we won’t be caught dead wearing a beanie anyway). Just please don’t wear it backwards.

We like this cappuccino hat from Vineyard Vines, but you can also find great options J Crew, Ralph Lauren and Barbour.

3. Flannels

Shirts, Jackets, Pajamas. Flannel is everywhere in the fall, and preppies can (and should) embrace it. Now, there is a time and a place for flannel. Don’t make this your Sunday best, or night out attire. But for some autumn bonfires, evening walks on the beach, or Saturday morning festivals, go for it! And don’t confine yourself to the standard flannels, flannel jackets are a great option as well.

The collection of flannels from KJP will never miss, but you can really find these at any dealer of preppy fabrics. Consider L.L. Bean, Land’s End, Faherty, and J Crew as other respectable options.

2. Embroidered Corduroy Pants

We’ve already said it, but corduroy is the fabric of the season for preppies (sorry flannel). You could call it the seersucker of autumn. Some might say adding the embroidered element makes them look tacky, but they are wrong. Sure, it’s a statement, but isn’t that what our style is about? Don’t be ashamed to rock some classic embroidered corduroy pants this October!

Sid Mashburn’s “Tree Of Life” cords are our favorite, but there are other options at KJP and Vineyard Vines as well.

1. Layered Rugby Shirts

You can tell this is the number one style of autumn, since it comes with instructions on how to wear it. Don’t just wear the shirt, but layer it! Throw it on over a polo or causal button down shirt for a stand-out look. But to layer it, you need to pick one out that fits great so be careful!

Our favorite option is the Ryder Cup Team USA rugby polo from Ralph Lauren, but L.L. Bean, Land’s End, and Marine Layer have excellent options as well.

Until next time,