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Located in the historic Fell’s Point area of Baltimore, Md., Cupcake Boutique (http://cupcake-shop.com/) has been dressing the women of Baltimore in the latest fashions for the last seven years.

With a focus on feminine, contemporary fashion at a good price, Cupcake’s clothes and accessories are always in style but never too trendy. Whether it’s a cute sundress for the Preakness InfieldFest, a sleek dress for the grandstand at Pimlico, or evening attire for a night on the town after the races, Cupcake has the perfect outfit for the occasion.


Owned and operated by Maryland native Lisa Schatz, Cupcake has been named the boutique with “Best Dresses” by Baltimore magazine five years running, as well as “Best Women’s Boutique” by Baltimore City Paper.

Before starting her own store, Lisa worked as both a buyer and visual manager for the popular Black Market-White House stores. Open seven days a week with plenty of metered parking spots right outside the store, your wardrobe won’t be complete without a visit to Cupcake Boutique (813 South Broadway, Baltimore, MD).

Lisa kindly took the time to talk to us about this year’s Preakness, and gave us her secrets for the perfect Preakness outfit. Her biggest advice? “Wear shoes you can wear for hours on end comfortably.” And don’t forget the sunscreen!

Mary Frances Dale: With the 138th running of the Preakness this Saturday, how will your boutique be preparing for the races?

Lisa Schatz: Because of the volume of sales … we are bringing in more products almost every day.  So dresses are going out the door and coming in at the same time! It’s crazy. We are attached to a hat shop, so the synergy is amazing this time of year. Sometimes customers buy the hat first, and we have to work backwards to match it. Sometimes they pick a dress first and we consult on the hat choice as well.


Mary: Throughout your time in Baltimore, has Preakness fashion changed over the years? 

Lisa: People have really stepped up their game. Most of the women in the grandstands will be in dresses and hats, and some of the ones in the infield as well. The men of Baltimore tend to be pretty fashion conscious as well, and they really turn it out, too. Seersucker, Bow Ties and Fedoras are a common site, as is the classic suit and tie.

Mary: What do you look for when creating the perfect race-day outfit?

Lisa: A statement in either the hat or the dress. Both can be too much … if the hat is bold, I generally suggest a classic sheath, or something solid in color. If the dress is printed and/or dramatic, then a simple elegant hat is best.

In addition, you have to watch accessories. If you are wearing a hat, earrings should be small, like simple studs, and sunglasses need to be small or understated. A fascinator will allow you to add somewhat more elaborate accessories, but you still have to be careful that your accents aren’t fighting one another.


Wear this classic dress to the Grandstand and pair with a statement fascinator.

Mary: How would you suggest dressing for the Preakness InfieldFest vs. the grandstand? 

Lisa: If you are in the infield, a short sundress is probably as dressy as you want to go. Avoid white and maxi-length dresses, the ground can get sloppy even in good weather. Wedges are ideal if you are going to be walking in the grass all day.


This sundress will keep you fashionable in the infield. Or dress it up with a hat and wear it to the grandstand.

Mary: What are you wearing to this year’s Preakness?

Lisa: Good question! I don’t actually know yet. I tend to wait until the last minute because if a customer wants to wear a style, I won’t wear the same one. Last year, I ordered a style from Milly for myself that I didn’t offer in the store, and Christine Moore made be a pillbox hat to match its retro silhouette. I am leaning toward an equestrian print mini dress with three-quarter sleeves by Julie Brown and a fascinator.

Mary: I can’t wait to see your outfit on Saturday! How many times have you been to the Preakness and what is your favorite part of the experience?

Lisa: This is my fifth year, and it’s been beautiful and sunny every time. In the first few years that our store was open, I worked on the Preakness day. But I have learned that while the week leading up to race day is CRAZY, the day of the Preakness is pretty mellow, so I let the girls run the shop and I go do my best to “advertise the store” on race day. I love to get pictures of my friends and clients in their ensembles at Pimlico and post them to social media. Many of my friends attend Black-Eyed Susan day Friday as well, but there is no getting out of Cupcake that day.

Mary: Have you been to any other Thoroughbred races?

Lisa: I have been to the Maryland Million at Pimlico. I will never forget when we met Jim Mckay and bowed to him. He embodied televised sports for us growing up. He was very cute about it. I would love to go to Derby next year.

I have also attended a lot of steeplechase races; they are very popular around here. 

Mary: Favorite fashion designers?

Lisa: All the lines we carry, but especially Milly, Black Halo, and Parker. My dream closet would have lots of Oscar de la Renta, Balenciaga, Balmain, and Chanel. I love the mix of uptown chic and edgy, downtown accents. High and low, casual and dressy.

Mary: What current spring trends do you predict will be popping up at this year’s Preakness?

Lisa: You will see lots of prints, high-low hems, lace, coral, mint, and pink.


This high-low hemline would be great for the grandstand.  Don’t forget a hat!


A bright peplum dress that could be at home in the grandstand or the infield.

Mary: What are your biggest fashion dos and don'ts?

Lisa: Biggest don’t: don’t buy something for its style if it doesn’t work on you. For example, I love huge sunglasses but look silly in them. I learned that lesson from looking at pictures of myself in college. Ugh.

Do: challenge yourself to try new styles and trends, regardless of age. Sure there are limits, but there is a way to pay homage to just about any fashion trend in a small way, without drastically straying from your personal style.

Mary: What is your best advice for all the ladies coming out to Pimlico this weekend? 

Lisa: Wear shoes you can wear for hours on end, comfortably. The walk to the bathroom alone is a hike. Wear sunblock, not because I am anti-tanning, but because many dresses will give you strap marks you will be trying to rid yourself of for a month. And, most importantly, if you are going to drink, take pictures early.


Perfect dress for the grandstand with some chic, yet comfortable nude strappy sandals.

All dresses pictured can be purchased at Cupcake Boutique (http://cupcake-shop.com/).

Image Description

Mary Frances Dale

A graduate of Sewanee: the University of the South, Mary has grown up riding and loving horses. Additionally, she has toured and managed musical artists with independent record labels based out of Austin, TX and brings excellent "road" knowledge to the ABRV team.

Image Description

Mary Frances Dale

A graduate of Sewanee: the University of the South, Mary has grown up riding and loving horses. Additionally, she has toured and managed musical artists with independent record labels based out of Austin, TX and brings excellent "road" knowledge to the ABRV team.

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