Destinations to Show Off Your Grandpa Core Outfits

Did you have grandpa fashion on your bingo card for 2024? Probably not. However, it’s not too late to win at the vintage-inspired style trend, “Grandpa core” that has dominated fashion Pinterest boards and TikTok thrift hauls this year.

From oversized knit sweaters, vintage glasses, wide pants, loafers, and even high waisted trousers, Grandpa core is gender neutral and can be achieved through sourcing clothes second-hand clothing, and also by purchasing high-quality items that will last a lifetime. Grandpa core is not just about dressing like a stylish grandpa, it’s also about creating a sustainable closet.

But what’s the point of having trendy Grandpa core outfits if you have nowhere to go? Luckily, we’ve created a list of top destinations based on activities that would pair perfectly  with your grandpa core style. Put on your oversized glasses and vintage loafers, and let’s go.

Strut your style around the Rose Bowl Flea Market in Pasadena, California

Who doesn’t love a classic treasure hunt? Channel your inner grandpa and go antique hunting at Rose Bowl Flea Market. Taking place in the iconic Rose Bowl Stadium, this flea market has been occurring for over 50 years in Pasadena, California. Rain or shine, you can expect over 2,500 vendors to gather on the second Sunday of every month to provide you with the opportunity to find your next treasure and grandpa attire. It’s the perfect place to throw on comfy trousers and find your next funky lamp or an original painting to put the final touches on your home space.

Book your stay at Best Western Pasadena Royale Inn & Suites.

Conveniently located just 15 minutes from the Rose Bowl Flea Market, the Best Western Pasadena Royale Inn & Suites is the perfect spot to book your stay. Guests also choose this hotel for its proximity to professional sporting events, libraries, botanical gardens, shopping, and more.

Catch a Movie at the Iconic Byrd Theatre in Richmond, Virginia

Between the matinee and senior discount pricing, grandparents love to catch a movie at the theater. So let’s take it a step beyond, and book a trip to Richmond, Virginia to enjoy movies at the legendary Byrd Theatre. Celebrating over 90 years of business, Byrd Theatre is recognized as a National Historic Landmark with the decadent interior design and architecture being continuously preserved and restored since its opening in 1928. Guests are able to purchase tickets for a variety of movies, from recent releases to shows that originally aired when the theater first opened its doors. Byrd Theater will be loved by the grandpa core individuals who appreciate a piece of history maintained to be fully enjoyed by generations to come.

Book your stay at Best Western Premier Richmond City Getaway

Stay at Best Western Premier Richmond City Getaway for a simple, 15 minute drive to the theater, allowing yourself plenty of time to arrive early and grab all the concessions necessary to enjoy the movie. The hotel location is also perfect for a stroll through famous Monument Avenue, and has easy access to cafes and galleries in the Fan District. It is the ideal place to stay and take a deep dive into the history of Richmond.

Grab a Pint at the Moon & Sixpence in Portland, Oregon

Ready to go for a freshly poured pint in a warmly lit pub? We believe most grandpas would reply with a strong “yes.” Well, the Moon & Sixpence is waiting for you in your chunky knit sweater in Portland, Oregon! The pub offers a full menu with beer, wine, spirits, and cocktails, so there is something for everyone. Not only that, but this traditional pub also offers live music three times a week, has a large outdoor patio, and boasts a collection of hard-to-find drafts. Time to put the book down, slip on those loafers, and enjoy a night of live music with pints that will have you feeling warm on the inside.

Book your stay at Hotel Eastlund, BW Premier Collection

After curling up with a good pint, Hotel Eastlund, BW Premier Collection will welcome you with elegant designer furnishings that convey classic style and modern sophistication. Located in Portland’s thriving Eastside, the hotel is a quick 10 minute drive to the pub of your dreams.

Bring Out Your Inner Birder in Harlingen, Texas

It should be no surprise that we’re including the top place to go bird watching when talking about style inspired by grandpa. During the fall migration, birders (what bird watchers are called) can sometimes spot 100 different species in just a few hours in Harlingen, Texas. Mark your calendars for the annual Rio Grande Valley Birding Festival, taking place this year in the fall. Grandpa core enthusiasts love their layers, and this fall activity is the perfect place to strut your style while checking off unique bird species you can spot through the best accessory –binoculars–like the colorful Texas resident: the green jay.

Book your stay at Best Western Casa Villa Suites.

Best Western Casa Villa Suites is the perfect home away from home that provides comfortable beds and southern hospitality. Book this charming hotel to be sure you get a good night’s sleep before a long day of bird watching.

Show off your Grandpa Core with Grandpa

For those lucky enough to still have grandparents around, our final recommendation is for you to visit them. At Best Western Hotels & Resorts, we’re all about making memories that will last, and we can’t think of anything better than spending time with loved ones. With over 4,300 hotels across the world, we might just have the perfect place for you to rest your head in between visits. Ask your grandparents questions you never have before, learn about their childhood and where they came from, and let them know that they are cared for and loved.  Maybe your grandpa will even let you browse through his closet for your next curated piece for your grandpa core aesthetic.