This week, Le Dress boutique in Wicker Park announced it will shutter at the end of September. Roam in Old Town is closing its doors for good on Sunday. What's it really like to own the local boutiques we love so much? Two store owners share why they've decided to move on.

When Mallory Ulaszek opened Cityblue Apparel & Denim in 2009, she was 24 years old. "I left corporate America on a whim," she says. "I really wanted to be in the fashion game." She dove right in, caught the interest of some investors with her business plan, and opened the doors to her Old Town boutique. "We had huge success in the first year compared to what our business plan was," Ulaszek says. "That was why I decided to open the second location in Lake Forest. On paper, it sounded like a really good idea."

Dividing her time between City Blue and the second store, CB, was taxing. Ulaszek made the decision to scale back in 2013 and close both locations. She imagined a new boutique filled with hard-to-find labels that would give her an edge over the big box stores. When Nicole Miller left her bi-level space on Wells Street, it was the perfect opportunity for Ulaszek to take over the space, start fresh, and rebrand with the name Roam—a nod to her love for travel and new adventures.

Roam was a great place to shop: We named it the best new store of 2014. Ulaszek supported local designers like Remi Canarie, C/FAN, and Jules. Diffusion lines like 10 Crosby by Derek Lam, Prabal Gurung IBC, and MM6 kept the store on-trend, while emerging designers such as Daniel Vosovic, Anine Bing, and Illesteva gave it edge. With black walls, exposed brick, and vintage fixtures, the space was very cool.

What happened next, though, is what Ulaszek calls "a perfect storm of shitty events." Setbacks pushed Roam's opening date to late October—the end of the fall. "It put us in off-season for fashion," she says. While Ulaszek retained many of her past customers, the new labels she carried had a higher price point than many were used to. "Rebranding was a huge risk, and it may not have been a risk that paid off," she admits. "But it was something I really wanted to do."

And then…the polar vortex. "We were closed 50 percent of the time between January and February," Ulaszek says.

The recent shift to online shopping didn't help, either. Ulaszek's little brick and mortar boutique was competing with global retailers who could slash their prices. Ulaszek says it's hard to for the little guy to win, but she cites Trunk Club as proof that local retailers can be successful if they’re innovative. "You have to have this very progressive, out-of-the box idea to really take it forward and really differentiate yourself," she says. "Because the competition is stiff."

After a string of tough months, Ulaszek made the decision in July to shutter the store. She began marking down prices, and now, almost everything is gone. There are still some pieces left–10 Crosby, Current Elliot, and MIH Jeans, to name a few brands–for those who want to snag a final deal at 75 percent off. Roam (1419 N. Wells St.) will officially close on August 31.

Ulaszek is taking the lessons she learned from owning three businesses and jumping right into a new venture. She and business partner Kelsey Kreiling have started Presence Agency, a marketing firm that helps businesses define their online identity through web design, social media, and events. The duo recently planned an album launch party for a local musician and is producing an event for foodies called Taste Talks this October.

"You don't ever look at it as a failure," Ulaszek says about closing Roam. "A lot of the people in the industry are just moving on and moving forward. I'm not the exception.”

Sister-in-laws and Le Dress owners Eva Anderson and Robyn Anderson Baldenegro were recently faced with a choice: renew the lease on their women's boutique for the next three years or move out—and on. They mutually decided it was time to let the store go.

"When we opened the store, it was just her and I living in the city. We had so much fun," Anderson says. Six years later, things are a little different. Anderson now has a four-year-old and two-year-old at home. Baldenegro is starting her own family and has moved to Naperville. "We're here every single day," Anderson says. "So we had to sit down and think if we could renew for another three years, and just realized that wasn't going to be feasible."

The decision is bittersweet, Anderson says. The co-owners have been through a lot together since opening Le Dress in 2008. "We literally opened right before the economy tanked," Anderson says. “It was very difficult to get through the first year. Vendors were going out of business, deliveries weren’t coming in, and people were dropping left and right."

They pushed on, adapting the store as their customers’ needs changed. What started out as a European-style boutique that solely carried dresses became a modern women's shop carrying everything from special occasion to weekend wear. I often recommend Le Dress as a sure-bet for a fun cocktail dress by brands such as Milly, Shoshanna, and Trina Turk.

But as it was for many small businesses, the winter of 2014 was a trying time. Le Dress suffered flood damage when a frozen pipe burst two floors above the store. "We ended up being closed for four months," Anderson says. "We had to rebuild our store."

They weren't the only ones. Perchance, a Gold Coast boutique that had been in business for seven years, never reopened after a pipe flooded the store in January. While this winter was particularly brutal, Anderson notes that she was always prepared for a slow, cold season. "The weather plays a huge role in a boutique," she says. "It's crazy because in Chicago you really have such a short great selling season: April through September."

Anderson wants the next generation of boutique owners to know it's not all gloom and doom, though. "If you go into it knowing how much work involved, it's really is a fun environment and a fun job. We loved every minute of it," she says. "Our lives just took a different turn."

Le Dress (1741 W. Division St.) will shutter on September 28, and the closing sale began this week. Inventory is marked at up to 75 percent off. Further markdowns will be taken in the coming weeks, but shoppers are encouraged to visit early and often for the best selection. The store will still receive its new fall shipments and items will immediately be discounted.