Sunday, 14 September 2025

Interview With Fashion Designer Allyson Mandelbaum

Hi There, my fashion savvy readers!! Women’s hats  — why are they always either too stiff, too boring, or plastered with cheesy slogans? Why do so many hats for women look like they were designed for sweaty baseball teams instead of stylish everyday life?


Picture provided by Allyson Mandelbaum

Believe me, I could have asked myself those questions years ago, when my mornings were a full-blown military operation. πŸ™‚πŸƒ‍♀️πŸ₯ͺ

I had two kids to help prepare for school, sandwiches to slap together, and me trying to look semi-human before work. Spoiler: I often failed. πŸ˜… πŸ₯ͺπŸ‘Ÿ

On one particularly tragic morning, I ran out the door with hair that could only be described as “experimental art”. πŸ™ƒ πŸŽ¨πŸ’¨

Of course, that was the day the office photographer showed up to take pictures for the company directory. Let’s just say, even now, decades later, that photo still haunts me like a ghost from the past. πŸ‘» πŸ“ΈπŸ˜¬

These days, my kids have left the nest, so no more sandwiches to make. My hair? Oh, it still likes to stage the occasional rebellion. Which is exactly why I was so curious to chat with fashion designer Allyson Mandelbaum. 😏 🧒✨

As a seasoned autumn chicken, I love anything that adds a little fun, style, and sass to life, and Allyson’s take on women’s hats does just that. πŸ” πŸ’ƒπŸ’–

In our interview, she reveals her playful, clever, and yes — a little shady — solution to the eternal bad-hair-day dilemma. 😎 🎩πŸ”₯


Picture provided by Allyson Mandelbaum

What is your name, function and the company you work for?  

My name is Allyson Mandelbaum and I’m the founder and CEO of Shady Lady

How old are you?

I’m 44 years old. 

What kind of work do you do, or what are you studying to be? 

I spent 20 years as a Reality TV Producer working on shows such as: My Super Sweet 16, 90 Day Fiance and Catfish before deciding to start my own women’s accessories company. 

What made you decide to become a Fashion Designer? Tell me about your journey.

I’ve always loved fashion and found it such a fun way to express myself but never thought it would become my career. However, after having two kids, I was always looking for an easy way to get out the door in the morning while still looking put together but not having the time to do my hair and get ready.

I was always jealous of my husband who could just throw on a baseball cap and walk out the door but I could never find a hat that fit me well. They were all too big, made my ears stick out or had funny sayings or team names on them. Where were all the cute fashionable hats for women? 

When my search came up dry, I decided to take matters into my own hands and start Shady Lady, the only company making hats specifically to fit women. We have since expanded to winter hats and tote bags with a bright, colorful, beachy aesthetic. 

Is fashion important to you? Why? 

Fashion is how I tell the world how I’m feeling inside. I know the eyes are supposed to be the windows to the soul but I think it’s what you are wearing. You are showing the world how you want to present yourself and if you look good, you feel good. 

Picture provided by Allyson Mandelbaum

What are your successes, and how did you achieve them?

In the 5 years since I started Shady Lady we have been featured on Good Morning America, the podcast, How I Built This and on the must have lists in Esquire, Life & Style and Intouch Magazines. 

My biggest successes have come from cold emailing people and telling them about the brand. We have a powerful message of empowering women by making hats specifically for them.

But the biggest success of all is seeing women in my hats and knowing they feel good about themselves. 

What’s something you might want to do in the future?

My goal is for Shady Lady to be the GO TO women’s brand for hats. Women’s heads are 2cm smaller than a man’s yet all hats are made from the measurements of a man’s head which is totally unacceptable. We plan on partnering with women’s sports teams, women’s gyms, schools etc to get women the hats they deserve! 

Is the name of the Brand important to you when you buy clothing or jewelry?

Quality is important to me and I trust certain brands to be a certain quality so I know what I'm paying for, but name alone means nothing. 

Describe your personal style of fashion?

My personal style is Boho chic. I take a lot of inspiration from 70’s California. I really like clothes that make people smile, that is always my goal when designing anything. 


How did you find your personal style? Do you have a signature look? 

I like to be adventurous and have fun with how I dress. It’s just clothing, you can change it the next day so why not have fun with what you are wearing. I also love wearing bright colors because they make me happy. The best compliment I can receive is when people tell me, “You are the only one who could pull that off.” To me it’s all about confidence in what you wear. If you feel good, you will look good! 

Do you have an influence on other people’s fashion style?

I like to post my outfits on instagram stories and love when people ask me for links or tell me I inspired them! 

Picture provided by Allyson Mandelbaum

What are in your eyes the best trends at the moment?

I’m all about looking cute and comfortable at the same time so I’m loving the sweatpant jeans. I can be comfy working all day but can also leave the house and feel like I’m not a mess. 
I’m always going to be a jumpsuit girl! It’s easy to throw on but always looks put together. 

What are in your eyes the worst trends at the moment?

Wide leg jeans are hard. I do love them but finding the right flattering pair is tricky. 
I’m definitely not into low rise jeans coming back, those were no one’s friend. It was hard enough to wear them during college, now that I’m in my 40s forget it, haha. I think Y2K fashion can stay in the past where it belongs. 

What kind of fashion advice would you give us?

Wear what makes you feel confident, that is always going to be how you look your best. And be adventurous, have fun with fashion! 

Who is your style icon, and why?

I love 70’s style icons such as: Bianca Jagger, Cher and Stevie Nicks. There was something so free about how they dressed. I always try to recreate that feeling. 

Is there something else you would like to share with us?

Don’t listen to fashion “rules” as they change daily, just have fun getting dressed. Don’t be afraid to stand out in a sea of black t shirts. 

Picture provided by Allyson Mandelbaum

A huge thank you to Allyson Mandelbaum for taking the time to chat with me! Your creativity, humor, and love for women’s hats truly shine through, and it was such a pleasure learning about your journey and inspiration. πŸŒŸπŸŽ©πŸ’–

Curious for more insider stories from the world of fashion? Don’t stop here! Check out our other interviews with talented fashion designers and get inspired by their creativity, sass, and unique perspectives. πŸ’ƒπŸ‘œ✨

Hope you like my blog.....Until next time.....Have a nice day 

Renata (Seadbeady) 

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