Birds of a Feather: Happy Hours
Welcome to the first installment of Birds of a Feather, a blog series that highlights amazing businesses in our community and beyond!
Ali and Redford on the Happy Hours stoop!
Ali Gilbertson is the one-woman show behind Happy Hours — hunting, curating, and staging a space that highlights the cool, the weird, and the beautiful. We are inspired by her eye and her love of community.
After a brief break this winter, Happy Hours will reopen its doors on March 1st, with a special soft-opening event on February 24th. We caught up with her for a brief Q&A to pick her brain on what inspires her and how she views the world of secondhand items.
How did Happy Hours get started? Why name it “Happy Hours”?
I moved back to the area after 9 years of managing a thrift shop in the east village of Manhattan. I longed to have a retail space of my own… but I refused to make (what I thought to be) the required commitment. It was important to me to work less hours than I had in NY, have flexibility, be able to travel and enjoy time with friends, my family and hobbies. I thought these goals and starting my own small business, surely, were mutually exclusive. I was wrong!
The bar that inspired the Happy Hours name.
When the pandemic hit, I lost my job and got creative. It became quickly apparent to me that if I was able to work on my own schedule, and focus on my strengths and what I enjoy most, I was able to be much more successfully productive. I started working on my branding and waited for the right space to pop up.
The name “Happy Hours” comes from the desire to combine the ideas of the bar I always thought I’d own one day and the thrift shop I actually came to want. I grew up in a family-owned bar here in Wisconsin, and from a very young age, my plan was to own my own bar one day. But then I became an adult and was like, that sounds awful. Anyway, my path led to a world of thrift and retail experience, but I wanted my personal brand to still hold the vibes and jukes of your favorite, local bar. I just… get to sell jeans, not manage anyone, and go to bed early.
What would you like for people to know about your shop?
A view from the shop — full of secondhand treasures handpicked by Ali.
The life and journey of these secondhand items I’ve collected and curated are important to me! I’m passionate about their past and ensuring they have a future.
Happy Hours is just me. While sometimes that can be overwhelming, especially on the days I could use another set of hands, it’s ultimately my goal to keep it that way. I think that it creates such a unique and personal experience for my audience and customers. What you’re seeing is my eye, I personally found and picked out everything you’re shopping, socials are all me, I drew the logo, I salted the stairs, you’re snuggling with my dog. I’m finding this makes it all the more rewarding for me and it feels less like work!
Who are some of your style heroes?
Ok, I feel like this is ‘outting me’ somehow, but— Carrie Bradshaw. Carrie Bradshaw og series.
90s movie heroines in utilitarian fits. Helen Hunt, Twister. Laura Dern, Jurassic Park. Meryl Streep, River Wild.
My parents! My parents in their 20s and 30s. I look at old photos and they were DRIPPING. And it’s extra fun because I see so much of myself in them AND I get to wear and sell a lot of their old clothes!
I’m trying to think what influences my home decorating style most… but it’s all over the board. Eclecticism at its finest.
What is your advice for people who are not sure where to start for secondhand or vintage pieces?
Do you like it? Do you feel comfortable? There you go.
What’s a typical week like for you as a secondhand shop owner?
Lol, next question.
I mean— honestly most days (unless there’s something on the calendar, and even then) I have no idea what’s going to happen. Thanks, ADHD! It can be anything from sourcing, building, yard work, cleaning, editing photos, taking a hike, Netflix, repotting plants, drinks with friends, laundry, tagging and pricing, to (wo)manning the shop.
There’s always a long list of things that need to be done, either at home or downtown. Recently having learned more about my neurodivergence and the way my brain works, I’ve come up with a loose system of each day running through the mega To Do List and when one jumps out at me as both exciting AND productive, that’s what I do.
The short answer: On any given day, it feels like mostly I’m either on Instagram creating content and/or doom scrolling or repeatedly loading and unloading my car.
What are some things you love about owning and running Happy Hours?
I’ve met so many new friends!
Any favorite secondhand finds?
Oh man. I can’t. Hahaha just about everything and anything around me is something I’ve thrifted, found scavenging or repurposed.
If I’m thinking clothing items, the first thing that pops into my head is a vintage Bloomer, Wisconsin blue corduroy FFA jacket that I found in a vintage shop while on a road-trip in Los Angeles. I love that thing. And it has been a top-notch conversation starter.
What are some of your go-to small businesses to support in Madison?
If a customer in the shop asks for another clothing store to hit, I always recommend Still Goods.
If they’re looking for art or furniture— Cozy Home.
Their next stop is a drink or a meal? Settle Down Tavern, Nattspil, Mint Mark, Imaginary Factory, or my personal favorite— Turn Key.
Any other secondhand wisdom to share?
In my opinion, collecting and being obsessed with “stuff” doesn’t necessarily make you materialistic. Our clothing and possessions are an expression, they are vibes, they represent you & make a home. I think it’s important to assign and invest value into our belongings and cherish them! Surround yourself with things you love. Just— be mindful of where and how you acquire them, and maybe most importantly, learn how to let go and pass things on when they no longer suit you.
You can visit Happy Hours on Fridays and Saturdays from 10 am - 6 pm starting March 1st. Be sure to check out the soft-opening event on February 24th. More information and tickets available through Instagram.
