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  • September 25, 2025 4 min read

    The Round Top Fall Show is almost upon us, which means the tiny town is about to bustlin’ with visitors and vendors alike, with a calendar packed with events, entertainment (like BINGO! *wink*), and fab fashion shows. Folks will be flocking to Round Top from all over the country in search of antiques, artwork, and one-of-a-kind fashion finds. And you’d better believe we’ll be there with bells on – and belts and bags and boots and toppers.
    Kennadee styling a vintage hand painted jacket and vintage hat in Round Top

    “There are no rules in Round Top!” laughed Cheryl. “It feels like playing dress-up but not actually dressing up. Claire, one of DDR’s designers, always jokes that she wakes up every morning and decides what character she’s going to be that day – Round Top is the place to play that game. Push the envelope, push your comfort zone, pair things that don’t necessarily make sense in your everyday. Load up, layer up, put on all your favorite accessories – and then add one more. It’s really a place to be fearless with your fashion.”

    EMBRACE THE ECCLECTIC

    Allow yourself to be expressive. If there’s a trend you’ve been wanting to try, Round Top is the perfect place to give it a test drive. Whether that’s barrel jeans, doubled-up belts, mixing power prints, or bringing those cargos out of retirement – give it a go! Truly, what’s the worst that could happen? Plus, no matter how ‘out there’ you feel before you leave your house, we promise when you get to the market you’ll feel right at home.

    CAP IT OFF

    You certainly don’t have to, but the reality of Round Top is that you’re going to spend quite a bit of time outdoors browsing antiques and markets and vendors and traversing from place to place, so it really is wise to add a topper to your look. A classic cowboy hat, a trendy trucker, or one of the new vintage-inspired newsboy caps – whatever suits your character for the day!

    Kennadee wearing vintag camo pants with a reworked vintage top, a trucker cap and layered jewelry
    VINTAGE VIBES & REWORKED CLASSICS

    This is *the* key to cool right now. If we’d have known our worn-out Wranglers and work-stained Carhartts would be so en vogue one day, we’d have stuck them in storage and we’d be in high cotton right about now! (Fortunately, we’re well-seasoned thrifters and we’ve been able to procure a stash you can shop – more on that below.) But it’s not just trousers, vintage anything can add a one-of-a-kind element – your camo from the ‘90s, your biker jacket from the ‘80s, your pearl snaps from the ‘70s (more on this, too!).

    Kennadee and Presley out shopping with their vintage bags to fill full of finds
    IT'S IN THE BAG

    Everyone heads to the Round Top markets in search of something different, but one thing’s for sure: you’re about to do some shopping. You’re going to want to browse with both hands, so pick a fuss-free-but-fabulous purse, like a vintage saddle bag or a tooled leather cross-body stirrup purse (we happen to make a great one… *wink*). If you plan to buy a lot of little items or load up on garb, there’s nothing wrong with bringing along a chic weekender or even a longhorn-clad laundry duffle.

    Kennadee layered for the day in a chambray shirt, vintage beaded vest, and tie.
    LIVE FOR THE LAYERS

    This can be tricky because South Texas temps don’t always wane when they’re supposed to (hello, why is it so hot in almost-October?!), but layering up is an easy way to experiment with your outfit and look lowkey-chic. Throw a vest on over a Henley, add a trendy tie or a statement bolo, layer on a leather jacket if the weather will allow it!

    CHIC SHOES YOU’RE READY TO WALK IN

    Ok, we know we said there are no rules in Round Top, but there is ONE rule: wear reasonable footwear. You’re going to be traversing some rocky dirt walkways and probably racking up some serious steps. We’re not saying ruin your ‘fit with your grass-stained gardening tennies, but definitely skip the heels or anything prone to causing blisters, and now is probably not the time to “try out those new shoes” for the first time. Stick with your tried-and-true boots, a pair of moccasin booties, or even chic sneaks that are all the rage right now.

    If you’re loving the look but feel like you’re missing a few key elements, come on in and see the girls at the store! Not only do they *get it* in terms of the ‘Round Top look’, but you might not know that our Round Top mercantile houses several items you can’t shop anywhere else.

    Kennadee styling a vintage jacket, belt, and hat for a chic Round Top look

    “I’m not sure people realize that there are a lot of exclusives in the Round Top shop,” Cheryl said. “For starters, our own vintage DDR pieces – things you can’t find in Fort Worth, we don’t sell online, not even at the Mothership. We’ve also started stocking vintage denim when we can find them, so if you’re looking to work some of that into your wardrobe, it’s worth a stop. And then maybe the coolest thing we’re doing right now is reworked vintage pearl snaps. We’re cutting them off and sewing in a drawstring, so it’s a cinched, cropped look that balances really well with the relaxed-fit pant silhouettes we’re seeing.”

    Round Top Fall Market kicks off on October 4th and we cannot wait to see what you wear!

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