It may be hard to believe, but Black Friday is just around the corner. The shopping holiday that traditionally kicks off the holiday season is often the biggest day for retailers, and the holiday season, lasting from Thanksgiving to Christmas, is the most important time of year in the industry, especially for chains that cater to gift-givers.

However, plenty of brick-and-mortar chains are struggling as the "retail apocalypse" continues to churn through the industry, with the rise of e-commerce and a change in shopping habits forcing some retailers into bankruptcy. Others have simply been slowly declining.

Below are four retailers teetering on the edge of relevancy, facing a make-or-break holiday season. Here's why the coming weeks will be crucial for J.C. Penney (NYSE:JCP)Macy's (NYSE:M)L Brands (NYSE:LB), and Gap Inc (NYSE:GPS).

A woman on her phone holding shopping bags

Image source: Getty Images.

1. J.C. Penney

J.C. Penney has been staring into the abyss for some time, ever since the company imploded in 2012 under former CEO Ron Johnson, whose misguided attempt to revamp the department store brand led to comparable sales plummeting 25% in one year.

Today, the company may be in even worse shape. Comparable sales are still spiraling downward, and the company has a $4 billion debt burden, hampering its ability to invest in its business to make a full comeback. But this holiday season is especially important for the retailer as it's the first one in which new CEO Jill Soltau, who joined the company a little more than a year ago, will be able to test her strategy for the company.

Soltau has jettisoned appliances and furniture from stores, reversing a move by predecessor Marvin Ellison, and is bringing back the company's traditional focus on apparel, private brands, and retail basics like visual merchandising. Penney also just launched Outdoor Shops for men at 100 stores, featuring a new private-label brand, St. John's Bay Outdoor, attempting to capitalize on a growth market.

The fourth quarter is also the only one in which Penney turns a profit, so it's especially important for the company to execute in order to get into the black and stay free-cash-flow positive. Through the first three quarters of the year, the company lost $532 million in free cash flow. 

Finally, the retailer needs to keep its stock price above $1 in order to avoid getting delisted from the New York Stock Exchange as the NYSE already gave it a warning.

2. Macy's

Few retailers are executing as poorly as Macy's these days. The department store chain just posted a comparable sales decline of 3.9% in the third quarter (on an owned basis), and slashed its earnings guidance for the year. The company now expects adjusted earnings per share of $2.57 to $2.77, down from a prior range of $2.85 to $3.05. Factoring out gains from the sale of real estate, Macy's expects EPS of just $2.20 to $2.40 for the year, down nearly a third from 2018.

Macy's shares are now trading in the low teens, having fallen 50% year to date, making it one of the worst performers on the S&P 500. CEO Jeff Gennette's job is likely on the line after the latest earning report and the stock's sell-off this year, making the holiday season especially important for him. Management did project confidence for the holiday season in its third-quarter earnings call, but it still sees comparable sales declining around 2% for the quarter.

The company has strengths, including a valuable real estate portfolio, and brands like BlueMercury and Story, but Macy's seems to lack an overarching strategy. If the fourth quarter is as bad as the third quarter, the stock will plunge again. The company can't lose profits like this for much longer.

3. L Brands

Victoria's Secret parent L Brands has been struggling for years. Over the last three years, the stock has lost 76% as consumers have moved away from Victoria's Secret and toward competitors like American Eagle's Aerie brand. With its supermodels and now-cancelled fashion show, the brand has appeared out of step with a changing culture in the #MeToo era, where sexualizing women in the way the brand's marketing has typically done has become frowned upon.

L Brands makes nearly all of its annual profit in the fourth quarter as lingerie is a popular gift item, so it's crucial that the company, which also owns Bath & Body Works, bounce back from a weak third quarter. That included a per-share loss that expanded from a loss of $0.16 to a loss of $0.91, and comparable sales at Victoria's Secret that fell 7%. 

For the fourth quarter, management expects earnings per share of $2.00, and it's forecasting full-year EPS of $2.40. If the company doesn't execute over the holidays, the stock is likely to crater again. 

4. Gap

The retailer that dominated apparel a generation ago is in disarray today. CEO Art Peck was forced out just a few weeks ago as Gap, which also owns Banana Republic and Old Navy, has badly underperformed the market in recent years. The stock is down 37% year to date.

With Peck's departure, the company's plan to spin off Old Navy, the discount chain that's been its top performer in recent years, is now in doubt along with the company's broader strategy. Its recent results show why the company is in desperate need of a new direction. 

Comparable sales fell 4% at the company and declined at all three of its major brands, slipping 7% at Gap, 4% at Old Navy, and 3% at Banana Republic. Adjusting earnings per share came in at $0.53, down from $0.69 a year ago. The company has been losing share to fast-fashion competitors like H&M and Uniqlo for a long time, but it's unlikely to mount a comeback until it names a full-time CEO.

With the holiday season right around the corner, Gap will have an opportunity to bring customers back, but with the shuffle happening among management, expectations are muted.