Scout Bags at Whimsicality


Exclusive Annapolis print tote bag.

I was so excited when Georgetown-based Scout Bags reached out to me recently. They sent over a couple of pieces to test out and wanted me to share more about their brand.

I felt like it would be the perfect opportunity to feature a local shop, Whimsicality, run by mother and daughter duo Tricia and Christine Hylind. Whimsicality is one of four Scout destination shops in the country and is located in Cape St. Claire.

Very few fashion brands are based in the area, so I'm always thrilled when someone chooses to invest in this community. Scout is a perfect fit for Annapolis- bright, functional, and well-suited for any activities on the water. 

I personally chose this striped Errand Boy tote bag, a major upgrade from my $1 Ikea blue bags, haha. I wanted the zipper top and structure for shopping trips. I have street parking downtown and often have to lug groceries many blocks. It's been working out great for me and isn't an eyesore in my apartment, which is a huge bonus. 

Scout couldn't have been easier to work with and I'm already eyeing new pieces, specifically this cooler for work lunches and/or wine.

I then set off to Whimsicality and was so pleasantly surprised by how friendly and knowledgeable they were. Christine and Tricia literally know EVERYTHING about all of their product lines, which is such a blessing and will be the saving grace of brick and mortar retail.

Christine and Tricia Hylind in their shop.

Would you please tell me a bit about the story of Whimsicality? Were you always interested in fashion and housewares?

Whimsicality was open & owned by Karen Anderson in 2004. In 2011, she sold the business to my mom, Tricia Hylind, who has been the owner ever since!

My mom has an incredible eye for fashion (if you’ve ever seen her wardrobe or stacks on stacks of jewelry, you would know!) She actually had been working at Whimsicality for Karen as a sales associate when Karen was going to close. My dad, knowing that Tricia always wanted to own her own clothing boutique, persuaded my mom to take it over!

I worked in retail all through high school at a children’s clothing boutique and then studied marketing and retail merchandising in college at the University of Maryland. When I graduated in 2013, I PRAYED that my mom would let me work there full time– and she did!

It’s been incredible working together and sharing our love for shopping, style, and fashion with the community!

What are your favorite parts about your job?

One- working with my mom. Truly don’t know what I will do when she decides to “retire” but I hope its not anytime soon! We share such a close bond and really are more successful when we are together!

And two- seeing hard work pay off. We carefully and tediously choose products to be featured at Whimsicality, and it's such an incredible feeling when clients ooo and ahhh over our product assortment. When customers leave happy and then come back telling us how well a gift went over with friends, we feel such a sense of pride.

It's also really fun to run marketing campaigns and social media pushes and watch them pay off directly through sales!

The window display right now at Whimsicality.

Describe the buying process and inspiration.

We do most of our buying at the Atlanta gift show. We go twice a year- the first trip is in January after the holidays have completely wiped us out. We purchase all spring and summer merchandise there. We go again in July to start buying for fall and holiday.

Although we do most of our buying at those two shows, we are ALWAYS on the lookout for new lines and brands that are innovative and chic. Sometimes we will come across a new product line on social media or from a customer. Locals will stop by with handmade art.

We love buying merchandise that is unique, coastal, funky, whimsical, and practical. We really try not to carry brands that are found in other gift shops nearby. It's the best to stand out with your own lines!

I see that you're expanding into the space next to you. What's next for Whimsicality?

We are absolutely over the moon about the expansion of Whimsicality. Any customer will tell you that the extra space is MUCH needed- we crammed all the product into such a tiny space.

We're thrilled to be able to go in deeper with certain brands and also bring in other lines that we have been eyeing for years now. There will be more efficiency (gaining another point-of-sale register!), better service (hiring more employees to run the shop with us that are friendly and knowledgeable), brand recognition (re-branding to be a bit more cohesive in all operations of the business), new products, and MORE SPACE! We will be able to host many more events for charity and promotions now, too!

Almost the full product line of SCOUT is in shop- this is just a small section of their display.

What are your personal favorite Scout pieces? Best-sellers?

Such a hard question – I am truly a Scout freak. I recently got married and I was talking to my husband before the wedding about what we would put on each other's cake if we did a grooms-cake and brides-cake. I had a million things to list for him – all of his favorite sports teams, his favorite foods and drinks, and images that mean something in his life. When I asked him about my cake, he sat there pondering for a few moments and said “Umm, I’d put on there bottles of wine and Scout bags." Most embarrassing moment or most proud moment? I do not know! Haha!

My favorite Scout piece is the Weekender. I prefer the bags that are softer fabric (it’s coated cotton) versus the stiffer material (polypropelene) that they also use. This piece is lightweight, perfect for trips (fits under the seat or above you in an airplane), has a zipper and inside pocket for money and a phone, and holds JUST the right amount for a short getaway, beach trip, you name it.

My next favorite piece is the Pleasure Chest Cooler. Unlike most coolers on the market, it is lightweight with longer shoulder straps- making it SO easy for a shorty like me to lug back and forth to a winery, pool, beach, or onto the boats. The shape of this cooler is unique, too– rectangular and stands up straight– perfect for stacking Tupperware and it will fit 4 (or 5) bottles of wine/champagne standing up!

We also love the BJ Bag. It has a stiff bottom, zipper closure, outside pockets, and an inside pocket. This bag is so great for towels in the summer time, sunscreen in the pockets, and money in the inside. Zip it up so sand doesn’t come in, and boom– perfect beach or pool bag!

What's your favorite thing about the Scout brand? There seems to be a lot of brand loyalty amongst their customers.

There are SO many things we love about Scout.

The first thing would really just be the people- they make the whole experience of working with them so much fun.

Deb and Ben (the owners) are innovative, forward-thinking, creative, intuitive, and practical. Besides being smart business people, they are kind, passionate, empathetic, friendly, and down to earth. There is no doubt that they channel these qualities in every employee they have.

Working with them is always such a blast and we really bounce ideas around with them. I think our relationship is a huge part of why Scout is such a success at Whimsicality.

I also love how Scout products can relate to any type of person. Their bags are functional and practical, first and foremost. Once you realize you need a beach bag or cooler that you can wipe clean, hose down, carry everything in, count on no leakage, and fold flat when it’s not in use, you then move on to the personalization of pattern.

Their patterns and color play are incredible. Someone with more preppy style might choose the pink and green polka dots, while someone with more of a sporty style might go for the thick navy blue and green stripe.

Then, you may have that woman who wears all neutrals and no color– and they’ve got a pattern she will love, too– you can count on it. They make everyone feel like the bag they choose is theirs and theirs alone because it exemplifies their own personality in a way.

What other brands and lines inspire you?

We have so many lines that we love– here are just a few.

S’well Bottle- funky colors & patterns.

Corkcicle– practical & functional.

Lafco Candle– classy, simplistic, and fragrant.

Annapolis Candle– nautical and run by a local husband and wife!

TJazelle Jewelry– handmade in Cape Cod and unique.

Hobo Bags– 100% genuine leather and such a high-quality product with vintage touches. Based in Annapolis!

Barefoot Dreams– comfy, cozy, and luxurious.

Sun Bum– a wonderful line for the body. Love their packaging, too!

Plus, all our local artists!

Favorite candle you carry?

Our personal favorite in terms of scent and brand is Smooth Sailing by Annapolis Candle.

Our best-selling candle is Volcano by Capri Blue – we can’t keep it in stock!

Most rewarding career moment thus far?

Probably the honor of being named a Scout Destination Store (there are only four in the country) and the launch of our exclusive Annapolis Scout bag. It went over crazy well and brought us so many brand new customers. It was so rewarding!

Most helpful piece of advice or guidance?

My dad always says “dare to be great”. It seems like a simple piece of advice but we truly put that mentality at the forefront of everything we do at Whimsicality. We take risks, sometimes huge ones, and they usually have worked out.

I think it’s important not to let a change in the economy, buying methods, community, etc. scare us. We are trying to be ahead of the game when it comes to unique gift-buying!

What are three things in your purse that you can't live without?

Christine– Chapstick, hair tie, prayer card.

Tricia- check book, reading glasses, money.

How do you relax after a long day?

We both love going out to eat! On any average day, though, we come home, change into comfy clothes, and pour BIG glasses of wine.

Favorite meal to cook at home? 

Christine– TACOS! (any kind!)

Tricia- Sausages with peppers and onions.

Standard drink order at bar?

Chardonnay for both of us!

Most frequented restaurant(s) in Annapolis?

Christine– Davis’ Pub.

Tricia– Cooper’s Hawk.

The most enjoyable thing about life in Annapolis?

The views, 100%! We love going to get dinner and drinks on the water. Living in this quaint little community feels like vacation even though it’s real life!

What's something most people don't know about you?

Christine– I changed my major 3 times in college! It all worked out though!

Tricia– She doesn’t wear socks with boots. Weirdo.