Social Outings
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Social Outings *
Stalwart Style Happy Hour
Welcome to The Stalwart Style Happy Hour!
A monthly gathering where men and women step out in their best Sharp/Smart Casual attire and enjoy great company at some of Baltimore’s swankiest spots. It’s all about getting to know your city, making new connections, and drawing inspiration from the well-dressed men (and women) in attendance.
Not sure what to wear? No worries—come as you are! Our image consultant friends will be on hand with advice, and we even host shopping trips between events to help any fella step up his style game.
🕛 When: Friday November 21st, 6-8 PM + Live Jazz afterwards…
📍 Where: The 1920 Social Club
✨ Good vibes. Great outfits. Better company. We’d love to have you!
Sharp Dressed Man Holiday Party
Hosted by: Sharp Dressed Man
We’d like to invite you to the 2025 Sharp Dressed Man Gala on Saturday, November 22, 2025, from 7:00–11:00 PM at the Baltimore Streetcar Museum. This signature event brings together community and business leaders to celebrate and support Sharp Dressed Man’s mission of empowering individuals to re-enter the workforce with confidence and dignity.
We also have a range of sponsorship levels designed to meet different visibility and engagement goals. Each level includes brand recognition before, during, and after the event, along with exclusive benefits the night of the gala.
Sponsorship Levels (summary)
Title Sponsor/Sharp Dressed Man Sponsor ($25,000)
Miracle Worker Sponsor ($10,000)
Gaming Sponsor ($7,500)
Bar/Beverage Sponsor ($5,000)
Food Sponsor ($5,000)
Impact Sponsor ($2,500)
Advocate Sponsor ($1,500)
Support Sponsor ($750)
Sharp Dressed Man is in need of your financial support. We’re currently fundraising to be able to hire a new executive director but we need your help. We have so many opportunities to take the Sharp Dressed Van into the community but we’re reaching our capacity on what we can do with volunteers only. Donations also help cover van maintenance, insurance, and utilities to sustain our mission.
Please consider making a financial contribution to Sharp Dressed Man so we can get the show on the road to help more people dress for job interviews and beyond. Alone we can do so little. Together we can accomplish so much. Thank you!
https://givebutter.com/vjSS56?gbtid=98a5f424b3c54f88b1431753fd525c6d
The SG Presents: A Night At The Theatre
A Night at the Theater
Twice a year, the lads suit up in their sharpest attire and treat the women and partners in their lives to an evening of culture and celebration. The night begins with dinner, drinks, and plenty of photographs at a stylish nearby restaurant (location shared with ticket purchase). From there, we take a leisurely stroll to the theater for a live performance—an evening of art, laughter, and great company.
A true display of appreciation for the ones we hold dear.
Annual FREE Suit Giveaway @ Sharp Dressed Man
Hey Stalwarts!
Our friends at Sharp Dressed Man—a non-profit that provides professional attire for men in need—just received a massive donation of suits, and they want to fit The Stalwarts’ Guild!
These are free, recycled suits (often surprisingly high quality). While tailoring will be needed, a future date will be set to get them adjusted just right. If supplies allow, you may even score a sport coat. Pro tip: bring a dress shirt or shoes if you want to see how your look comes together.
🕛 When: Sunday December 14th, 12–3 PM
📍 Where: Sharp Dressed Man HQ
A perfect chance to upgrade your wardrobe and support an incredible mission. Hope to see you there!
FREE Suiting @ Sharp Dressed Man
Hey Stalwarts!
Our friends at Sharp Dressed Man—a non-profit that provides professional attire for men in need—just received a massive donation of suits, and they want to fit The Stalwarts’ Guild!
These are free, recycled suits (often surprisingly high quality). While tailoring will be needed, a future date will be set to get them adjusted just right. If supplies allow, you may even score a sport coat. Pro tip: bring a dress shirt or shoes if you want to see how your look comes together.
🕛 When: Wednesdays, 12–2 PM (the only time this offer is available)
📍 Where: Sharp Dressed Man HQ
A perfect chance to upgrade your wardrobe and support an incredible mission. Hope to see you there!
The SG’s Seasonal Gentlemen’s Dinner
The SG’s Seasonal Gentlemen’s Dinner
The Stalwarts’ Guild began with men coming together around proper attire and fine dining in the great city of Baltimore! We continue our seasonal tradition, and it shall remain a private, invitation-only affair. One must learn and grow to be offered a seat at the table, and we look forward to having you once you’re ready!
🕛 When: November 8th, 5–10 PM
📍 Where: to be disclosed…
Stalwart Style Happy Hour
Welcome to The Stalwart Style Happy Hour!
A monthly gathering where men and women step out in their best Sharp/Smart Casual attire and enjoy great company at some of Baltimore’s swankiest spots. It’s all about getting to know your city, making new connections, and drawing inspiration from the well-dressed men (and women) in attendance.
Not sure what to wear? No worries—come as you are! Our image consultant friends will be on hand with advice, and we even host shopping trips between events to help any fella step up his style game.
🕛 When: Friday October 17th, 5-10 PM
📍 Where: The Brewer’s Art
✨ Good vibes. Great outfits. Better company. We’d love to have you!
FREE Suiting @ Sharp Dressed Man
Hey Stalwarts!
Our friends at Sharp Dressed Man—a non-profit that provides professional attire for men in need—just received a massive donation of suits, and they want to fit The Stalwarts’ Guild!
These are free, recycled suits (often surprisingly high quality). While tailoring will be needed, a future date will be set to get them adjusted just right. If supplies allow, you may even score a sport coat. Pro tip: bring a dress shirt or shoes if you want to see how your look comes together.
🕛 When: Wednesdays, 12–2 PM (the only time this offer is available)
📍 Where: Sharp Dressed Man HQ
A perfect chance to upgrade your wardrobe and support an incredible mission. Hope to see you there!
Stalwart Style Happy Hour
Welcome to The Stalwart Style Happy Hour!
A monthly gathering where men and women step out in their best Sharp/Smart Casual attire and enjoy great company at some of Baltimore’s swankiest spots. It’s all about getting to know your city, making new connections, and drawing inspiration from the well-dressed men (and women) in attendance.
Not sure what to wear? No worries—come as you are! Our image consultant friends will be on hand with advice, and we even host shopping trips between events to help any fella step up his style game.
🕛 When: Friday September 26th, 5-10 PM
📍 Where: Mama Koko’s
✨ Good vibes. Great outfits. Better company. We’d love to have you!
Fall Sale on Summer Men’s Wear @ Dolce Vita Leathers & Fashions
Style Meets Smart Spending
Looking sharp matters—whether it’s for social outings, first impressions, or the world of dating. But looking good shouldn’t mean draining your wallet. The move? Snag top-quality pieces on sale.
We’ll be rolling through to support a local men’s clothing shop and scoop some Summer staples for next year. Expect premium brands at up to 60% off.
Pull up if you’ve got time—browse some great deals, hang with the fellas, and maybe grab a bite after.
FREE Suiting @ Sharp Dressed Man
Hey Stalwarts!
Our friends at Sharp Dressed Man—a non-profit that provides professional attire for men in need—just received a massive donation of suits, and they want to fit The Stalwarts’ Guild!
These are free, recycled suits (often surprisingly high quality). While tailoring will be needed, a future date will be set to get them adjusted just right. If supplies allow, you may even score a sport coat. Pro tip: bring a dress shirt or shoes if you want to see how your look comes together.
🕛 When: Wednesdays, 12–2 PM (the only time this offer is available)
📍 Where: Sharp Dressed Man HQ
A perfect chance to upgrade your wardrobe and support an incredible mission. Hope to see you there!
Stalwarts’ Guild Seasonal Dinner
The Stalwarts’ Guild began with men coming together around proper attire and fine dining around the great city of Baltimore! We continue our seasonal tradition, and it shall remain a private, invitation-only affair. One must learn and grow to be offered a seat at the table, and we look forward to having you once you’re ready!
Stalwarts' Book Study
Our Book Study is dedicated to reading the best non-fiction books to learn more about the ourselves and the world around us. Reading a few chapters at a time, taking notes, and discussing what we’ve learned to begin applying it in the real world.
Philosophy, finance, dating, war, evolution, social skills, psychology, survival, and biographies are all on the table. Let us know what interests you!
Upcoming Session: picking the next book to read and going through the foreword and introduction. We will announce it through our platforms if you’d like to read along! Contact us if you’d like to meet us in person.
Stalwart Style Happy Hour
Welcome to The Stalwart Style Happy Hour! A monthly gathering for men and women to dress themselves in Sharp/Smart Casual attire and enjoy good company at some of the swankiest spots in Baltimore. Get to know your city while getting inspired by the well dressed men in attendance!
Don’t have anything to wear? Come on out regardless and chat with our image consultant friends to get good advice. We even do shopping dates in between these events for any fella looking to look his best! We’d love to have you!
Sharp Dressed Man Suit Fitting
Hey there lads! Sharp Dressed Man is a non-profit that takes suit donations and fits gentlemen who need them for work, interviews, presentations, etc. They recently received a massive donation and would like to fit The Stalwarts’ Guild to help spread the word about their organization!
Consider that these are free recycled suits, usually of an interestingly high quality. While free, they will require tailoring; future tailoring date will be set once finished. If supplies are available, you may also get a sport coat. Optional to bring a dress shirt/shoes to see how they’ll fit with your suit.
Yes, Wednesdays from 12-2pm is the only time this offer is available! We’d love to have you if your schedule can swing it!
Stalwart Style Happy Hour
Welcome to The Stalwart Style Happy Hour! A monthly gathering for men and women to dress themselves in Sharp/Smart Casual attire and enjoy good company at some of the swankiest spots in Baltimore. Get to know your city while getting inspired by the well dressed men in attendance!
Don’t have anything to wear? Come on out regardless and chat with our image consultant friends to get good advice. We even do shopping dates in between these events for any fella looking to look his best! We’d love to have you!
Sharp Dressed Man Suit Fitting
Hey there lads! Sharp Dressed Man is a non-profit that takes suit donations and fits gentlemen who need them for work, interviews, presentations, etc. They recently received a massive donation and would like to fit The Stalwarts’ Guild to help spread the word about their organization!
Consider that these are free recycled suits, usually of an interestingly high quality. While free, they will require tailoring; future tailoring date will be set once finished. If supplies are available, you may also get a sport coat. Optional to bring a dress shirt/shoes to see how they’ll fit with your suit.
Yes, Wednesdays from 12-2pm is the only time this offer is available! We’d love to have you if your schedule can swing it!
Stalwart Style Happy Hour
Welcome to The Stalwart Style Happy Hour! A monthly gathering for men and women to dress themselves in Sharp/Smart Casual attire and enjoy good company at some of the swankiest spots in Baltimore. Get to know your city while getting inspired by the well dressed men in attendance!
Don’t have anything to wear? Come on out regardless and chat with our image consultant friends to get good advice. We even do shopping dates in between these events for any fella looking to look his best! We’d love to have you!