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Meet Lesley Timpe of Squasht Boutique in West Town

Today we’d like to introduce you to Lesley Timpe.

Squasht is both a store and a clothing brand. Squasht designer Lesley was trained at Maestro Mateo Design School in Spain. She brings a European vibe to her apparel and accessories designs. All Squasht brand garments are conceptualized, designed and created from start to finish locally in Chicago. Signature pieces include endlessly wearable modern-vintage style dresses and reversible handmade hats. She has been named “best local clothing designer” in the Chicago Reader “Best of Chicago” Readers Polls.

Squasht Boutique, a brick-and-mortar storefront in the West Town/ Ukrainian Village neighborhood of Chicago, carries all of the seasonal Squasht collections. The boutique also carries a wide selection of independent designer wares from around the nation, including women’s apparel of all kinds, accessories, and jewelry. Squasht Boutique was named one of the “Best Boutiques in Chicago” by Culture Trip in 2017. The shop and the collections are available at: Squasht Boutique, 2556 W. Chicago Ave, Chicago, IL 60622 or online at

Squasht is totally devoted to supporting handmade and independent labels, with a strong focus on Chicago-made clothing and jewelry. Every season, they create and produce their very own collection of women’s ready-to-wear clothing and signature reversible hats right in the city. They are also extremely passionate about supporting their fellow artisans, which is why they proudly carry a wide selection of the work of dozens of other independent designers. Unique jewelry, hats, knitwear, dresses, separates, tees, leggings and lots of other charming surprises can be found! Shop Local. Shop Handmade. Shop Squasht.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Haha! A smooth road? – Nope! The struggles are real, but as a business owner the only way to succeed is to keep going and keep your head high.

Some of the main struggles that I have personally faced as an independent designer and business owner are: trying to compete with big-box businesses and internet stores, cash flow crunches, all kinds of production issues & fabric issues, and trying to wear too many hats as the sole designer and owner of my own company.

Squasht has a rather crazy business model encompassing many categories, such as wholesale, retail, events, and more. It can be really hard to juggle it all.

However, there is a lot of beauty in our story as well. When customers really appreciate what you are bringing to the table, it truly does make it all worth it. We have garnered so many devoted friends and customers who keep us in business. Our business is here for -and because of- our customers, and their appreciation keeps us alive and kicking.

Please tell us about Squasht Boutique.
Our company is really pretty unique! We specialize in handmade apparel and accessories and our store carries almost exclusively independent-brand designers. Squasht is also well known for our handmade reversible hats. Our brand Squasht is created from concept to creation in Chicago, so that is definitely a point of pride for us.

We are able to offer a very high quality product that lasts a long time at a price that is reasonable and accessible. We are known for our customer service and attention to detail, as well as our high quality products. Everything in the shop is carefully curated and hand-selected. At the same time, we keep in mind that people don’t want to (or can’t) spend $600 on a dress, no matter how cool it is. Almost everything in our shop retails for under $150. Most of our jewelry is under $70. This offers our customers the best of both worlds: high quality, handmade and special pieces at very do-able prices. I think this is what I take the most pride in. We never want our customers to feel gouged or taken advantage of. We love and respect our customers so much. We also offer free alterations on our Squasht brand apparel, which makes owning a perfect-fitting dress a no-brainer.

If you had to go back in time and start over, would you have done anything differently?
My path has been unique and I wouldn’t want to change it. I own my own company and am able to work every day in a beautiful storefront. I was able to study fashion design in Spain which was one of the highlights of my life. To be honest I am very happy and wouldn’t change a thing. I have just been loving my life lately and practicing a lot of gratitude.


  • Squasht Reversible Handmade Hats $58
  • Squasht Handmade Dresses $108 – $148
  • Handmade Jewelry by Various Designers $12 – $80

Contact Info:

Image Credit:
Gunnar Curry
Lesley Timpe

Getting in touch: VoyageChicago is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

1 Comment

  1. Sally Schwartz

    October 6, 2017 at 11:32 pm

    Lesley is such a talent and though I love vintage and designer fashion, the pieces I have by SquashT are some of my favorite and most comfortable pieces of clothing. Congrats to keeping a great biz going and here’s to many more years of fab creations!

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