How to Do Preppy Style Over 50: Chic Ways to Wear It Now

It seems like every few seasons the preppy look comes back around to the mainstream; that said, for many of us it never left. Whether you are a preppy die-hard or love an occasional argyle sock or popped collar moment, preppy style can be a fun source of wardrobe inspiration or a lifestyle choice—or anything in between.

How To Wear Preppy Style Over 50

There are some key elements of the preppy handbook that work on any age, like stripes, seersucker, houndstooth or herringbone blazers, madras, and monograms. Sportier pieces like boat shoes, varsity jackets, and anything equestrian-inspired are also welcome, as are simple pearl or diamond (or moissanite) studs. 

Preppy Looks To Avoid

However, there are some preppy looks that are best avoided once you’re past, say 30 or 35.  This includes styles that skew overly young, like wide headbands, hair ribbons and bows, or pleated skirts (especially if they’re plaid). Combinations that can read as matronly, like boxy polos or cardigans paired with a short 16 or 18 inch pearl necklace, are also best skipped. 

Here are some of our favorite ways to pull a little preppy flair into your wardrobe this fall.

Tailored Blazers

The archetypal navy blazer—perhaps with a medallion or monogram, or gold buttons like the prototypical Ralph Lauren versions —works in a variety of situations. Camel blazers can also be wardrobe workhorses (elbow patches optional) along with anything that evokes riding jackets. We especially love these styles worn with more casual pieces, since they can elevate a simple tee and jeans into an “outfit”. 

Want to score a great preppy blazer for a steal? The J.Crew schoolboy blazer is available at the Factory store for under $125 in navy, camel, or black.

Penny (Inspired) Loafers

Loafers are having a moment, whether you add the actual penny or not. They’re a great base for this season’s silhouettes, especially in chunkier styles like these from Calvin Klein that ground the volume in wide leg denim or trousers.

Prefer something a little sleeker? Frye makes this classic style that’s available in a bunch of rich brown and tan shades. 

Rugby Shirts

A step up from sportier quarter-zips, rugby shirts might be the perfect casual fall layer for when a hoodie is too casual but jackets aren’t quite necessary. You can find them at any price point and colorway really, but we like the wide stripes and chunky knit of this one from Lioness via Revolve. 

Cable Knits

These knits come around every fall and while they’re never out of style, they’re definitely being refreshed and remixed in new ways this year. Think cropped shapes that hit at a flattering spot on the waist, chunky turtlenecks and polo necks (try this one from Lacoste). 

There’s even cable knit hoodies that look super warm and perfect for crisp afternoons this one from Uniqlo. 

Collared Shirts as the Foundation

Wearing a button-up shirt on its own definitely fits into the preppy style equation, but they also make excellent layering pieces. Wear them underneath the aforementioned cable knit sweaters or under sweatshirts and tees (both long and short sleeved) to dress up some more casual pieces. 

Pull out the striped, checked, and solid button-ups you already own or pick up some new ones for under $20 from Old Navy—if you’re just going to layer them, only the collar and cuffs really matter. 

Modern Chinos

Remember the simple flat-front khakis we loved in the 90s? Those are back and they still work, both as part of a minimalist ensemble (pair with them a simple black or white tee) or as a neutral basic to ground brighter or bolder tops. Keep it sleek with this high-waisted pair from Spanx.

Or go slightly slouchier with these pleated Aritzia trousers. 

Barn Jackets

The barn jacket (they’re also called chore jackets, work jackets, field jackets, or utility jackets if you’re searching for options) comes back around every fall, but it’s definitely more popular than usual this year. 

This ubiquity makes right now a great time to invest in a new one, especially if you’re looking for something different than the denim and leather jackets that are always suggested as a cool weather layer. We love this Sézane version with velvet details.

Or try this jacket from The North Face for a sportier take. 

Preppy Style: Mixing It Up

If you enjoy some aspects of the preppy look but don’t want to go full Brooks Brothers or J. Crew catalogue, we love mixing in a few more subversive accessories, like a studded cross body bag or belt with an otherwise buttoned up look, black or chrome nail polish, or perhaps a skull ring like this one from Alexander McQueen. Just one or two small touches that lean more punk or grunge than polished or traditional go a long way towards keeping preppy ensembles from looking frumpy. 

Do you love the preppy look? Or does it give you high school or college flashbacks? What are your favorite preppy pieces to mix into your wardrobe? Do you prefer a more streetwear-inspired or edgy version of prep style, or do you stick to the classics? Let us know in the comments or on our Growing Younger Facebook page! 

–Jacqueline Zenn

You may also like to read more of Jacqui’s styling posts like Belts are Back: 7 Ways to Define Your Waist in 2025 and Top It Off: Layers for Summer Into Fall (That Aren’t Denim Jackets).

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