Stylist and Round Top Finds™ contributor Whitney Would shares her rules for shopping, styling and surviving a day at Round Top.

Stylist Whitney Would knows her way around a vintage rack and around Round Top. Her approach mixes the practical with the pieces actually worth hunting, from the boots that can handle eight hours in the fields to the vintage denim worth trying on regardless of what the tag says.

Ahead of Fall Show, we asked Whitney what she would and wouldn’t do at Round Top. Here’s her list.

WHITNEY WOULD 

1. Would wear boots you can stand in for 8 hours! While you can always get your boots shined afterward, wear something you’re ok with getting dirty. I often gravitate toward a round toe boot for those long days of walking and shopping! A few I've worn to Round Tops past have been either vintage, my Frauleins or my CITY Boots for a fun but comfortable flare!

2. Would ask the dealer/vendor if there’s a story behind a piece. Half of Round Top’s magic is the provenance!

3. Would bring a tote or wagon. You will buy more than you think and carrying multiple bags or going back and forth to drop off your stuff in the car isn’t feasible. Also, not every vendor, especially in the field, has bags to offer. If I'm going out to dinner after and need to plan accordingly, I'll pack a small purse or pouch that fits only the essentials and throw it in my tote to use for the evening's festivities. My favrite tote was actually a custom order from Nikki Stitch She embroidered some fun personalized things on a massive tote for me! She takes orders via instagram DM's! 

4. Would try on vintage denim even if the tag size looks wrong. Vintage sizing runs completely differently! Don't let the tag deter you! Levi's are my first stop - specifically the 501s. I'm checking the tag for the big "E" on the red tab (that's your signal it's pre-1971, the good stuff) versus the small "e" from later runs. Either way, 501s are the gold standard because the fit and the fabric weight have never really been replicated since.

I'm also always digging for Levi's orange tab - a lot of people don't realize that line existed alongside the classic red tab, and it tends to run a little more relaxed through the leg, which makes it a great everyday vintage fit.

I also love to wear the 912's - they're slimmer through the hip than a 501 but keep that rigid, structured vintage denim feel. If I find a pair in my size, I'm buying it on the spot.

On the Wrangler side, I'm always looking for the 936PWD - it's the boot-cut workhorse of vintage Wrangler, and it's become a favorite because it splits the difference between the too-slim modern fit and the boxier vintage cuts that don't flatter every body.

A couple of general tips I always tell clients: check the tag placement and stitching style (that tells you the era), and don't judge a pair by the size on the tag - vintage sizing runs completely different from what we're used to today, so always try them on before ruling them out. 

Insider secret: Grailed Garments at Zapp Hall has been my go to for extremely fair priced vintage denim!

Would pack a cooler with some refreshments in the trunk! Fall Show can be really hot and having food and water with you is important. Most venues have concessions but having food and water with you is the safest bet. I love packing these snackle boxes for a little charcuterie on the go! And some Rose Gold Rose to have on hand just in case!

6. Would look for natural fibers (cotton, wool, silk, leather) over synthetics. They’re the pieces that last and re-sell! My friend Anna from Mercer Vintage has incredible tips on how to care for your vintage finds (getting out old smells, washing silks, etc.) Example here

7. Would go for the leather belts, boots, and bags first. Best-quality vintage leather goods move fast. I'm a belt junkie and have found some of my favorite belts and buckles in Round Top! I'm always looking for belt straps with snaps to interchange buckles.

11. WOULD seek out the small designers! Round Top offers an incredible opportunity to discover new brands and with individualism returning to style, this is a great way to explore designers that speak to you and your style! 

A few of my fav designers I've discovered in RT are Semplice Designs, Volta Atelier, Leather & Vodka, The G's Knees (her new collection of shimmy's are insane), and Shapeau!

12. WOULD - Lately, I'm hunting in two directions at once: discovering new independent designers and makers I haven't sourced before (for myself and for client styling), and digging for niche vintage - think 70s silk dresses, hand-tooled leather belts, and one-of-a-kind silversmith turquoise pieces you won't find twice. That mix of "brand new to me" and "impossible to replicate" is what keeps Round Top exciting every season.

13. WOULD - Dress western without it feeling costume. My rule for Western without costume: start simple - solid denim, a white tee - and let one traditionally Western piece do the talking, like a vintage belt or a bolo. Build from there one piece at a time instead of stacking it all on at once.

14. WOULD - if I could only buy 3 pieces for Fall Round Top: a great leather jacket (bonus points for fringe), a pair of quality vintage boots, and one standout accessory that feels personal to me!

15. WOULD recommend my formula for a great Round Top outfit: one vintage anchor, one modern basic, and one accessory that's a little unexpected - you can build from there! Beyond that, anything goes - Round Top is the place to get playful with your personal style and try the combination you've been too nervous to wear anywhere else.

16. WOULD bring an added layer to throw on just in case. Weather during shows can be iffy in the morning/evening so I always like to have a jacket on hand! My Sapana Tara Crop Jacket  is my RT layer of choice!

17. Would not skip sunscreen or a hat. You’re outside all day and not always in the shade. I'm either wearing a cowboy hat or my Sissy Light and always wearing this on my face!  It's got great coverage but light as a feather so you don't feel heavy on the makeup!

18. Would not haggle on anything handmade by an artisan. If someone crafted it themselves, that craft is likely their livelihood, and the price reflects real time and skill, not markup. But I would feel comfortable negotiating with dealers on vintage and antique pieces. Just remember these are real businesses too, so skip the lowball offers on anything already fairly priced. Best rule of thumb: bundling multiple pieces is usually where you’ll find room to flex, not haggling one item down.

19. Would not go without a plan. Round Top is massive. Pick 2-3 fields to focus on each day, or you'll burn out before you get to the fun part: the hunt itself. My personal strategy: start in Warrenton and work your way up. That's usually where I find the best deals, so I avoid blowing my budget early and coming up empty-handed when the real gold shows up further up the road.

20. WOULD NOT purchase leather items that have stains, mildew, or structural damage - those don't fix. What I'll overlook: a missing button, a loose hem, or a little surface wear- easy fixes that don't affect the integrity of the piece.

21. WOULD NOT - one thing I see at Round Top that I personally wouldn't do: buy a piece just because it's a fun one-time moment. I always think about cost per wear - if it's not something I'll actually reach for again outside of Round Top, I skip it. The best vintage finds earn a permanent spot in your closet, not just one wear.

22. WOULD NOT overpay for mass-produced "vintage-inspired" pieces priced like the real thing - if it's not actually vintage, it shouldn't carry a vintage price tag.

Most of all for the final stop on Whitney's list, Whitney wouldn't be afraid to get to know the vendors! They're there to share their craft, so ask questions and be kind. You never know who you'll meet - if you're a regular at the show, I promise some of those vendors turn into lifelong friends. 10/10 recommend.

Instagram: Whitney Would