Do you remember The Official Preppy Handbook? A friend recently unearthed a copy in his garage, and all of us 80’s kids began to wax nostalgic. I never was a preppy. In fact, I was decidedly anti-preppy, but of course, I had the handbook. We ALL had the handbook.
Gingham check is the epitome of preppy style along with pink & green and Sperry Top-Siders. For that reason, I avoided gingham for most of my life. Recently, I have been drawn to the simple check pattern. Though my style is more classic than in my youth, I still recoil at being too preppy. I have tattoos for goodness sake!
J.Crew Gingham Shirt
Did you know, the J.Crew founder Arthur Cinedar found inspiration in The Official Preppy Handbook in hopes of capitalizing on its success? The evolution of J.Crew from preppy to fashion mainstream happened under Jenna Lyons, and that is when I became a J.Crew fan. Feeling the pull of gingham combined with a newfound love for button-up shirts, I picked up a The Classic-Fit Boy Shirt in gingham check at my local J.Crew.
My goal is to work this traditionally preppy shirt into my modern casual style. Here are three outfits to inspire you to add gingham to your wardrobe. Preppy or not!
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Outfit #1: Gingham Shirt + Cargo Pants + Retro Sneakers
First, I added my gingham shirt to joggers and sneakers. The Sanctuary Cargo Joggers fit my casual vibe. They are so much my style; I bought them in every color. I wish they were just a bit longer length then I could wear them year-round. To keep the look casual, I only tucked one side of the shirt and let the rest hang and added some retro Reebok kicks, which are crazy comfortable. My shoes are no longer available, but Reebok Club C Double Sneaker are super similar.
My bracelets are from Ubuntu Life, an ethical shoe and accessories brand handmade with love in Kenya. These bracelets look great alone, stacked with other Ubuntu Life jewelry or with your favorite gold or silver pieces. They just launched the VOTE beaded bracelet, which I can’t wait to add to my collection. The bracelets add a boho vibe to the whole outfit.
Gingham Shirt / Cargo Pants / Sneakers (similar)
Outfit #2: Gingham Shirt + Ripped 501 Jeans + Sandals
Next, I paired my Gingham shirt with my favorite ripped pair of Levi’s 501’s. I am obsessed with light wash denim this year. For fall, I am on the hunt for the perfect pair of light wash skinnies. Check back to see what I find. In the meantime, I am rocking these destroyed 501’s.
This outfit has a little bit of a Mary Ann from Gilligan’s Island feel, especially with the knotted shirt, which is definitely not preppy. I am not sure it is 100% me, either. I am more of a city girl. The shoes are the issue, but they are so comfortable. Next time, I would swap the sandals for a pair that is edgier like these or these.
Gingham Shirt / Jeans / Sandals
Outfit #3: Gingham Shirt + Cargo Jacket + Skinny Jeans + Sneakers
Pretty much anything army green is my style. I collect utility jackets. Not necessarily intentionally but because I am drawn to them. They are the perfect layer year-round in SoCal. You can wear them with a tank or layered over a sweater. Utility jackets are one of my most used pieces in my wardrobe. The one I am wearing is from Anine Bing and is sadly no longer available. This Amo Utility Jacket is almost identical, though. I also have the Madewell Passage Jacket in black and olive. The cost per ware CPW on this jacket is crazy low. I wear it All. The. Time.
The utility jacket toughens up the gingham. I kept the shirt tied, but you could easily tuck and wear with a belt. I added my obsessing over light wash denim and some high top sneakers. This outfit is pretty much my everyday uniform back when I could run out on a whim. Remember those days? We will be back there someday. Fingers crossed.
Shirt / Jacket (similar) / Jeans / Sneakers
The J.Crew gingham shirt is lightweight and perfect for the transition to fall. In winter, I will wear this shirt peeking out over my favorite oversized grey sweater. There are countless ways to incorporate this pattern into your wardrobe without venturing too far into Preppyville.
If you are thinking – what is wrong with being preppy? Absolutely nothing. Some of my favorite celebrities dress preppy, including Reese Witherspoon and Taylor Swift. I love the look. It just not my style. Most of my style rests on my gut instinct. I usually get a feeling about something and decide I got to have it. This shirt was one of those things. Maybe there is a little more inner-preppy in me than I thought.
I would love it if you followed me on Instagram for my everyday outfits or on Pinterest for my fashion inspiration. StyleDahlia is a fashion and lifestyle website with a modern take on midlife. We hope to inspire you to step out of your comfort zone, try new things, and live your life in full bloom.
