Step Into Summer Events: What to Wear When Heels Aren’t Practical

Outdoor event season is one of our favorites, and also one of the trickiest when it comes to shoes. Because the reality is… grass, gravel, and uneven surfaces don’t care how cute your shoes are.

While outdoor weddings often take center stage, this year we're excited to partner with the Belmont Bourbon Bash, Central Pennsylvania’s premier bourbon and culinary experience benefiting the STAGES Foundation. As part of their race-day celebration, their team stopped by Plum Bottom for a photo shoot on what to wear to an outdoor event and it sparked a conversation we have with customers all the time.

What should you wear to a wedding, a shower, or any outdoor event where you want to look great, but also be comfortable?

Why We Keep Coming Back to Wedges & Chunky Heels

Let’s just say it plainly—this is not the season for stilettos .If you’ve ever sunk into the grass or carefully tiptoed across gravel, you already know why.

Wedges and chunkier heels give you that lift you want, but with the kind of stability that lets you actually relax. You’re not thinking about every step. You’re not scanning the ground while balancing a drink and a plate. You’re just enjoying the experience!

Flats that Feel Event Ready

If heels aren’t your thing—or you just know you’ll be on your feet all day—flats are absolutely in the conversation this season. The key is choosing a pair that still feels intentional and event-ready. 

Practically speaking, flats are a dream for outdoor settings—easy to walk in, no sinking into grass, and comfortable from the first step to the last.

The Styles We’re Reaching For Right Now

If you’re someone who wants a little height but refuses to sacrifice comfort, wedges are where it’s at.

You'll put on NAOT wedges and immediately understand. The cork footbed, the arch support; their wedges are built to be worn for hours. Not just walked in, but lived in for an entire event.

 

Andre Assous gives you a slightly dressier version of that same idea. The Neena wedge, especially in metallic leather, hits that sweet spot where it feels elevated enough for an event, but still easy to wear. It’s polished without trying too hard.

If you lean a little more tailored, a chunky heel might be your better fit.

The Vaneli Cyndia is a great example of that. It has structure, it feels a bit more refined, but the heel is solid and grounded. You’re not balancing—you’re walking normally. That alone changes your entire experience at an event.

And then there are the styles that bring a little personality into the mix. 

The retro-inspired strappy sandals from Regarde le Ciel have that slightly vintage feel that makes an outfit more interesting. The heel is lower, the look is a little more unique, and they’re the kind of shoe people notice in a good way.

We’re loving woven flats from All Black, especially in metallic leather. They have that texture and subtle shine that elevates the look, so you don’t feel underdressed. 

Or enjoy the raffia menswear inspired flat from Django and Juliet.  It's just as perfect with a pant suit as it is with a long floral dress. 

Whether you go for wedges, chunky heels or flats, the best part is, they don’t feel like a compromise. The styles we’re seeing right now are clean, modern, and easy to dress up or down.

The Part People Don’t Always Think About

When your budget is a factor (and really--when isn't it?!) it doesn't always make sense to purchase a shoe for a single outfit or event. But when you buy a comfortable wedge or chunky heel, you’ll want to wear them again and again.

A great wedge works just as easily with jeans as it does with a dress. A chunky heel can go from a wedding to a dinner out. Even the more styled pieces can carry you through the rest of the summer.

If you’re going to invest in something, it should have a life beyond one afternoon.

A Local Event Worth Getting Dressed Up For

If you are looking for an excuse to put together a great outfit, the Belmont Bourbon Bash is one to have on your calendar.

It’s happening Saturday, June 6 at Ironstone Ranch at Stone Gables Estate—an elevated race-day experience built around bourbon tastings, incredible food, live music, and yes… a little fashion.

We’re proud to be part of it this year. We’ve several gift certificates for their raffle, and for the silent auction, we’ve created something really special—a private evening shopping experience for up to 8 guests. Everyone receives a $25 store credit along with a Plum Bottom swag bag filled with some of our favorite things.

It’s a fun night out, but it also supports the STAGES Foundation, which makes it even better. STAGES supports individuals, families and caregivers navigating serious illness.  It's the kind of care that we'd all hope for in our toughest moments. 

We are so excited about the event, that we've invited our staff! Both stores will close at 4pm on Saturday, June 6th so that we can enjoy and evening out together.

Final Thought

The goal isn’t just to look good for the event. It’s to feel comfortable enough that you forget about your shoes entirely and just enjoy where you are. 

At Plum Bottom, we want you to feel as good as you look.  Let us help you find the perfect pair at either location in Harrisburg or Camp Hill, or browse our website for more ideas. 

You can get tickets to the Belmont Bourbon Bash here.