Men

Born of friendship, intention, fashion, and fitness, Jake Gyllenhaal and Heartbreak co-founder, Dan Fitzgerald, teamed up for the Run Well, Do Good capsule collection.

While filming the movie “Stronger," the story of author and survivor Jeff Bauman, Jake Gyllenhaal immersed himself in the culture of Boston. He captained the Boston Medical Center Boston Marathon Team, threw out the first pitch at a Red Sox game with Jeff, and ran a few hundred miles with Heartbreak co-founder, Dan Fitzgerald.

When it came time to host the "Stronger" premiere, true to his reputation of elevating deeper stories by leveraging his status, Jake hosted the premiere at Spaulding.

In recognition of the 10 years since the Boston Marathon bombing, the classic gym-wear capsule will raise money for Spaulding Rehabilitation. In the wake of the 2013 Boston marathon, Spaulding treated 32 of the most critically injured survivors, including Jeff. Patients received world-class clinical care, emotional support, and physical training as they navigated the healing process. 

Product Details:

• 100% Polyester
• Inner brief with elastic leg openings
• Self-binding fabric on the hem

~ $45 per pair of shorts will be donated directly to Spaulding (65% of the retail price)

Don't let cold weather stop you from getting in your miles. The Heartbreak Halsted Headband keeps your head warm and comfortable.

The contoured design extends to cover your ears for extra coverage. As an added benefit, reflective details improve visibility in low-light conditions for added safety.

Product Details:

One Size Fits Most
90% Nylon, 10% Spandex

Don't let cold weather stop you from getting in your miles. The Heartbreak Halsted Beanie keeps your head warm and comfortable. As an added benefit, reflective details improve visibility in low-light conditions for added safety.

Product Details:

One Size Fits Most
90% Nylon, 10% Spandex

The energetic “RUN!” is inspired by two sides of the same wall - one inside the club, the other in the alley. Polish & punch. Beats & synth. Rhymes & dreams.

“The Firehouse” is Heartbreak’s staple singlet. Its lightweight wicking fabric makes you feel light & cool while you’re tackling miles. Heartbreak’s ethos of “make it matter, make it fun” is imbued in design touches throughout the garment. The name comes from our flagship store’s marquee training run and the fire station located at Commonwealth Ave & Washington Street in Newton that marks the first turn of Boston’s legendary marathon. Like that challenging loop, this singlet is Heartbreak’s standard bearer. Whether it’s the foundation of your Boston training or a core wardrobe staple, the Firehouse is a necessity.

Product Details:

• Screen printed front.
• Raised Heartbreak patch on back.
• Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - the connecting forces between runners.
• Reflective Heartbreak logo center back.
• Heartbreak flag logo at side seam.

Lightweight. Breathable. Wicking. 
90% Polyester, 10% Spandex

Heartbreak's 2023 Boston collection celebrates the first-timers, the goal-setters, and the big-believers. Goals must be verbalized so why not say them loud? Make some noise for your dreams! 

“The Firehouse” is Heartbreak’s staple singlet. Its lightweight wicking fabric makes you feel light & cool while you’re tackling miles. Heartbreak’s ethos of “make it matter, make it fun” is imbued in design touches throughout the garment. The name comes from our flagship store’s marquee training run and the fire station located at Commonwealth Ave & Washington Street in Newton that marks the first turn of Boston’s legendary marathon. Like that challenging loop, this singlet is Heartbreak’s standard bearer. Whether it’s the foundation of your Boston training or a core wardrobe staple, the Firehouse is a necessity.

Product Details: 

• Screen printed front.
• Raised Heartbreak patch on back.
• Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - the connecting forces between runners.
• Reflective Heartbreak logo center back.
• Heartbreak flag logo at side seam.

Lightweight. Breathable. Wicking. 
90% Polyester, 10% Spandex

The energetic “RUN!” is inspired by two sides of the same wall - one inside the club, the other in the alley. Polish & punch. Beats & synth. Rhymes & dreams.

“The Firehouse” is Heartbreak’s staple short sleeve. Its lightweight wicking fabric makes you feel light & cool while you’re tackling miles. Heartbreak’s ethos of “make it matter, make it fun” is imbued in design touches throughout the garment. It takes its name from our flagship store’s marquee training run and the fire station located at Commonwealth Ave & Washington Street in Newton that marks the first turn of Boston’s legendary marathon. Like that challenging loop, this singlet is Heartbreak’s standard bearer. Whether it’s the foundation of your Boston training or a core wardrobe staple, the Firehouse is a necessity.

Product Details: 

• Screen printed front.
• Raised Heartbreak patch on back.
• Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - connecting forces between runners.
• Reflective Heartbreak logo center back.
• Heartbreak flag logo at side seam.

90% Polyester, 10% Spandex

A sporty classic with fashionable flair, the Heartbreak Pom Knit Beanie is a cold day essential. From the heart patch on the front to the pom pom on top.  It's a heavier-weight winter hat that you can wear anywhere, style it as you see fit.

Groundbreakers, pacemakers, shot-takers, Heartbreakers.

Heartbreakers celebrate diversity of pace & person. We believe in the connective power of running to break down socioeconomic, ethnic, and religious barriers. We are beginners, Olympic trialists, international competitors, first-time 5K runners, and best-time everything runners. We are people who run, committed to getting better & committed to the success of each other. 

Membership includes your first Team Singlet, a pair of Heartbreak Midweight Crew Running Socks, and a Halsted Hat when you join. Hat and Crew Sock colors may vary based on seasonal availability.

Heartbreaker Firehouse Singlet

“The Firehouse” is Heartbreak’s staple singlet. Its lightweight wicking fabric makes you feel light & cool while you’re tackling miles. Heartbreak’s ethos of “make it matter, make it fun” is imbued in design touches throughout the garment. The name comes from our flagship store’s marquee training run and the fire station located at Commonwealth Ave & Washington Street in Newton that marks the first turn of Boston’s legendary marathon. Like that challenging loop, this singlet is Heartbreak’s standard bearer. Whether it’s the foundation of your Boston training or a core wardrobe staple, the Firehouse is a necessity.

Product Details:

• Screen printed front.
• Raised Heartbreak patch on back.
• Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - the connecting forces between runners.
• Reflective Heartbreak logo center back.
• Heartbreak flag logo at side seam.
• The garment hang tag includes red shoe laces with tips that read “Love” on one end and “Heartbreak” on the other.

Lightweight. Breathable. Wicking.
90% Polyester, 10% Spandex
The garment runs small. We recommend sizing up.

Halsted Run Cap

A rubber stamp logo centers the front. On the back, is a small red embroidered heart and bartacks in black, red, and white that symbolize road, blood, & spirit, respectively. Logo-printed interior taping, nylon strap closure & plastic buckle, and a reflective "Heartbreak" word mark on the side round out the package.

Product Details:

90% Nylon, 10% spandex

Midweight Crew

• 200 needle count
• Heel tab for no-slip
• Seamless toe
• Moisture-managing
• Y-heel construction

80% Dry-Release, 17% Nylon, 3% Spandex

Midweight Crew Sizing

Run Hard, Risk Heartbreak. Represent Heartbreak wherever you go. The line that "breaks" the heart is the elevation profile of the world-famous Heartbreak Hill. Designed by runners, made for runners. Train, run long distances, or take a walk with no worries about your socks causing any discomfort. 

Product Details:

• 200 needle count
• Seamless toe
• Moisture-managing
• Y-heel construction

The Hampton quarter zip is a training staple for cool weather. The perfect outer layer for cool fall mornings or a warming mid-layer for freezing climates, the Hampton is our favorite weight for a quarter zip. It feels bouncy and warm with cozy thumbholes and wide, bright reflectivity at the shoulders and zipper.

The Hampton features signature brand touches like the black, red, and white bartacks over the left wrist and our rubber stamp logo at the left chest. We call it the Hampton after Hampton Beach, NH, the place where our founders Justin and Dan shook hands on their initial partner agreement and developed the original logos.

Product Details:

• True to size.
• Mid-weight. Breathable. Wicking.

87% Polyester, 13% Spandex

The Good Times Full Tight is our signature men's tight made-to-move. Designed for performance on the go, we loaded it with pockets so that you can load it up with essentials. The Good Times features large pockets on each hip for your phone, gels, sunglasses, or other quick-access necessities. Stash valuables like your credit card or keys in the secure zip pocket at the back.

The name Good Times is a nod to our former Boston area GM Benny Goodtimes who sets the vibes at "glorious" for anyone who comes through our flagship store at Heartbreak Hill.

Product Details: 

• Two large hip pockets (one on each hip)
• One large zip-back pocket
• Heartbreak rubber stamp logo at left hem
• Heartbreak flag logo at right side seam

Fabric content 90% nylon, 10% spandex

The Distance Carryall is our go-to, go-everywhere waist pack. Made for phones of all sizes, keys, or run nutrition. It's sleek, rides well, and makes sure that your stuff goes the distance with you.

Product Details:

80% Nylon, 20% Spandex

“The Lincoln” is Heartbreak’s minimalist staple singlet. Its lightweight wicking fabric makes you feel light & cool while you’re tackling miles. Heartbreak’s ethos of “make it matter, make it fun” is imbued in design touches throughout the garment. The name comes from our Chicago store's neighborhood: Lincoln Park. 

Raised Heartbreak patch on chest.
Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - the connecting forces between runners.
Reflective Heartbreak logo center back.
Heartbreak flag logo at side seam.

Product Details:

True to size.
Lightweight. Breathable. Wicking.
90% Polyester, 10% Spandex

The Elevation Long Sleeve brings a fresh design twist to a classic running look. The seam across the chest matches the elevation profile of the famed Heartbreak Hill. (Just like the line in our logo.) Elevate your run & bring a tailored sophistication to it in this premium short sleeve. Carry the spirit of one of our sport’s iconic places with the Elevation Short Sleeve. 

Product Details:

The garment runs true to size with an updated fit.

• Raised Heartbreak patch on the left shoulder.
• Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - connecting forces between runners.
• Reflective Heartbreak logo center back.
• Heartbreak flag logo at side seam.

90% Polyester, 10% Spandex

The Elevation Short Sleeve brings a fresh design twist to a classic running look. The seam across the chest matches the elevation profile of the famed Heartbreak Hill (just like the line in our logo). Elevate your run & bring a tailored sophistication to it in this premium short sleeve. Carry the spirit of one of our sport’s iconic places with the Elevation Short Sleeve. 

Product Details:

The garment runs true to size with an updated fit.

• Raised Heartbreak patch on the left shoulder.
• Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - connecting forces between runners.
• Reflective Heartbreak logo center back.
• Heartbreak flag logo at side seam.

90% Polyester, 10% Spandex
Reid is 5’10”, wearing Medium

The Elevation Singlet brings a fresh design twist to a classic running look. The seam across the chest matches the elevation profile of the famed Heartbreak Hill. (Just like the line in our logo) A fabric inset over the right shoulder calls to mind a captain’s patch and is ready for your customization.

Elevate your game, elevate your style, and carry the spirit of one of our sport’s iconic places with the Elevation Singlet. 

Product Details:

The garment runs true to size with an updated fit.

• Raised Heartbreak patch on the left shoulder.
• Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - connecting forces between runners.
• Reflective Heartbreak logo center back.
• Heartbreak flag logo at side seam.

90% Polyester, 10% Spandex

“The Firehouse” is Heartbreak’s staple singlet. Its lightweight wicking fabric makes you feel light & cool while you’re tackling miles. Heartbreak’s ethos of “make it matter, make it fun” is imbued in design touches throughout the garment. The name comes from our flagship store’s marquee training run and the fire station located at Commonwealth Ave & Washington Street in Newton that marks the first turn of Boston’s legendary marathon. Like that challenging loop, this singlet is Heartbreak’s standard bearer. Whether it’s the foundation of your Boston training or a core wardrobe staple, the Firehouse is a necessity.

Product Details: 

The garment runs true to size with an updated fit.

• Raised Heartbreak patch on back.
• Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - the connecting forces between runners.
• Reflective Heartbreak logo center back.
• Heartbreak flag logo at side seam.

Run Hard, Risk Heartbreak. Represent Heartbreak wherever you go. The line that "breaks" the heart is the elevation profile of the world-famous Heartbreak Hill. Designed by runners, made for runners. Train, run long distances, or take a walk with no worries about your socks causing any discomfort. 

Product Details: 

• 200 needle count
• Heel tab for no-slip
• Seamless toe
• Moisture-managing
• Y-heel construction

95% Nylon, 5% Spandex

Run Hard, Risk Heartbreak. Represent Heartbreak wherever you go. The line that "breaks" the heart is the elevation profile of the world-famous Heartbreak Hill. Designed by runners, made for runners. Train, run long distances, or take a walk with no worries about your socks causing any discomfort. 

Product Details:

• 200 needle count
• Heel tab for no-slip
• Seamless toe
• Moisture-managing
• Y-heel construction

80% Dry-Release, 17% Nylon, 3% Spandex

“The Firehouse” is Heartbreak’s staple singlet. Its lightweight wicking fabric makes you feel light & cool while you’re tackling miles. Heartbreak’s ethos of “make it matter, make it fun” is imbued in design touches throughout the garment. The name comes from our flagship store’s marquee training run and the fire station located at Commonwealth Ave & Washington Street in Newton that marks the first turn of Boston’s legendary marathon. Like that challenging loop, this singlet is Heartbreak’s standard bearer. Whether it’s the foundation of your Boston training or a core wardrobe staple, the Firehouse is a necessity.

• Screen printed front.
• Raised Heartbreak patch on back.
• Black, red, & white bartack stitches at the side seam represent road, blood, and spirit - the connecting forces between runners.
• Reflective Heartbreak logo center back.
• Heartbreak flag logo at side seam.
• Garment hang tag includes red shoe laces with tips that read “Love” on one end and “Heartbreak” on the other.

Fit notes:
Light weight. Breathable. Wicking.
90% Polyester, 10% Spandex
Elijah is 5’9”, wearing Medium

Both highly functional & down to party. Put it on your head and go about your business. 

"Halsted" is a reference to our first Chicago community hub at 2148 N Halsted St. in Lincoln Park.

Product Details:

A rubber stamp logo centers the front. On the back, is a small red embroidered heart and bartacks in black, red, and white that symbolize road, blood, & spirit, respectively. Logo-printed interior taping, nylon strap closure & plastic buckle, and a reflective "Heartbreak" word mark on the side round out the package.

90% Nylon, 10% spandex

Run Hard, Risk Heartbreak. Represent Heartbreak wherever you go. The line that "breaks" the heart is the elevation profile of the world-famous Heartbreak Hill. Designed by runners, made for runners. Train, run long distances, or take a walk with no worries about your socks causing any discomfort. 

Product Details: 

• 200 needle count
• Heel tab for no-slip
• Seamless toe
• Moisture-managing
• Y-heel construction

80% Dry-Release, 17% Nylon, 3% Spandex