How to Shop for Owensboro's Dress for Less Gala

No high fashion! Just high impact.

Those are the words to live by this Sunday night in Owensboro, Kentucky. The Owensboro Convention Center will play host to the first-ever Dress for Less Gala to benefit Catholic Charities of the Diocese of Owensboro. Earlier this week, I spent some time getting dressed for this special event for less! Here's how I did it.

My friend Ashley (who I 'hired' to be my very own official photographer/paparazzi) joined me at Goodwill on Hwy 54 here in town. My goal was to find an entire outfit (head to toe) that I could wear to emcee the gala. I was challenged by Catholic Charities Executive Director Susan Montalvo-Gesser to do just that. I replied to that challenge on social media with this- "It's already been brought." As of this story, I can amend that to "It's already been BOUGHT!"

Goodwill came through like a "dress for less" boss. Here are some photos from several outfits I put together as possibilities.

Since the Dress for Less Gala is taking place in the middle of summer, I thought it may be a good idea to waltz into the convention center looking like I was about to embark on a cruise ship. What do you think about this?

I actually LOVED that outfit. But, I have to be honest. That jacket was a touch small. I like a slim fit, but it was a 40. I typically wear a 44 and can, occasionally, squeeze into a 42. But that particular coat was serving Silence-of-the-Lambs straightjacket. However, I was living for that shirt. So, I bought it anyway.

Get our free mobile app

I also found something that screamed "ski resort!" Since the idea of the gala is putting together some 'high fashion' for cheap, I flirted with the idea of rocking this winter 'Swiss Alps' classic.

I am obsessed with that pullover. Heck, it even has an emblem of Kentucky on it. But, it was freaking HOT! I thought I was going to spontaneously combust if I didn't get that thing off my body. Side note. That made for a really hilarious moment in the dressing room when I got stuck in the sweater and had to have Ashley run in and save me from it. I think all my sweat made it stick to me like Saran Wrap. I suppose I should issue apologies to the person who ends up buying it.

Now, here's the outfit that was a solid 2nd place.

If you were to consult ChatGPT and ask it to show you a photo of a shirt that screams "Chad Benefield", it would show you that precise shirt. I have about ten other shirts in my closet (okay, maybe fifteen) that look just like that one.

The only reason this outfit failed to win the day is because I wasn't crazy about the tie. Otherwise, that look would have been your winner.

Instead, I used some of the same pieces and decided on this.

I am OBSESSED! Naturally, I had to do a full photo shoot.

Let's break down the total cost of this master class.

JACKET: $8.99

SHIRT: (It had a yellow tag, so it was half price!!) $3.00

JEANS (which were BRAND NEW with tags, by the way): $9.99

SHOES: $4.99

TIE: $1.99

TOTAL COST: $28.96 plus tax

Clearly, I 'dressed for less' and am ready to rock out my gig emceeing A Dress for Less Gala, Sunday, July 26th in Owensboro.

If you'd like to go, tickets are still available! Doors will open at 5pm with a cocktail hour. The event begins at 6pm with dinner, a special presentation, and awards. At 7:30, dancing gets underway with DJ Prof G. There will also be A Dress For Less fashion show with prizes!

So, get ready to strut your thrifted stuff. I definitely will be. All $28.96 of it.