Women in Business Feature

You Can Leave Your Hat On

WOMEN IN BUSINESS SPOTLIGHT: You Can Leave Your Hat On, a visit with Sandra for Women’s History Month

If you’ve been to downtown Oregon City, Oregon, it’s very likely you’ve walked past or have stopped inside You Can Leave Your Hat On.

After spending many years being a legal investigator, Sandra Gillman, owner of You Can Leave Your Hat On, wanted lighter work and started her hat shop in 2011.

Her store is located on 7th Street, in the heart of Oregon City, Oregon, near the municipal elevator. 

Sandra wears many hats, including wife, mother, and grandmother; and when she’s not running the store you can find her taking morning walks with her grandchildren, getting lost in a good book, and travelling around the world with her husband.

She has been to almost all of the continents, and can’t wait to visit places again, once it’s safe to do so. In fact, many of the photos that hang inside her shop were found while travelling overseas.

Sandra loves her little shop and has a strong appreciation for her customers, many who return hat after hat. 

“My customer’s brighten my day,” says Sandra, adding that her “customers are probably the best part of my business as they bring joy into the shop.” 

It’s true her customers feel the same way, because when you first step into her store, you’re met with a collage of polaroid prints of happy shoppers showcasing their new headwear. Each one displaying a beaming smile from ear to ear!


“Never, never give up. You will have great highs, and great lows. You just have to realize that you will have the lows and you will survive them.”

When you stroll by You Can Leave Your Hat On, you might think her shop is only filled with Kentucky Derby hats, but you’ll be pleasantly surprised to see an array of all styles when you step inside. 

You’ll find different sun hats, beanies, fedoras, and more; in addition, there’s a range of mens hats to choose from as well. 

Whatever the reason is for stopping in, there’s a high possibility you’ll find your perfect match here. Sandra is knowledgeable, friendly and wants nothing more than to find that perfect fit for your head. She really enjoys helping her customers feel confident.

Like many other small businesses, this past year has been difficult. Through government shutdowns, snow/ice and the wildfires of 2020, business has been slow; she mentions the community has been so supportive, saying, “I have a lot of returning customers that have come back just to keep me alive. I appreciate them so much.”


“I’ve learned that I do have some advantages being a woman.”


“Well there are two things that inspire me and motivate me. Those two things are God and my husband.”

You can tell she loves what she does, and it doesn’t go unnoticed. One of her customers said in a review, “what a great shop.  Great selection.  The most awesome steampunk hats!  The owner is so sweet and wonderful!!!! Make this a stop when in OC”

Prior to COVID-19, champagne is the first ingredient for a great time in her store. Sandra loves having this on hand for her customers coming through the door, and every hat purchase comes with a sweet treat… chocolate! You don’t often hear of that kind of welcoming.

These are the small but intentional touches you will feel being inside her shop. After all, “a hat is like the wink after a sentence,” says Sandra. 

How to get connected and support You Can Leave Your Hat On

Support Sandra’s store by stopping by for a hat at 212 7th St, Oregon City, OR 97045 

Visit You Can Leave Your Hat On on Facebook

Visit and reach out through her website or hang out on Instagram 

Written and photographed by Ashleyann Burnett, of Simple Shot Photography, who is a volunteer with DOCA. Here is her story about visiting with Sandra. 

“I walked into You Can Leave Your Hat On and felt so welcomed by Sandra. I told her right off the bat, that I never felt like a hat person (you can tell she has heard this before). After trying on a few hats, and browsing and photographing her shop’s space, I couldn’t help but think about one sunhat in particular. Perfect for my days in the garden, I just had to have it, so I bought it! I guess I actually am a hat person, after all. 🙂 Sandra is knowledgeable, friendly and welcoming. If you catch yourself saying what I said, see Sandra. Because there is a hat for all of us! It was lovely getting to meet with her.”