by Gini Ogle

View winning envelopes from past years:


“Scripsit” magazine of past winning envelopes

Themes of past contests






Graceful Envelope Contest
Call for Entries

hand*Note judging has been delayed until October

Download 2022 CALL for ENTRIES flier
Postmark deadline: Monday, March 21, 2022.

2022 theme:
Greetings & Salutations

Whether somebody has written Hey there, Hello, Hola, Wuz up, Cher ami, Hi, or Good day, those lines launch the kind of connection you can’t get from an email or a tweet.

Celebrate the magic of beginning to read (or write) a personal letter! Make sure your submission reflects artistic hand lettering and an imaginative use of color and design. Try to incorporate postage stamp(s) into your creation. The contest, conducted by the Washington (DC) Calligraphers Guild, is open to all, everywhere, with separate categories for children.

Address your envelope/entry to:
The Graceful Envelope
P.O. Box 3688
Merrifield, VA 22116
Postmark deadline: Monday, March 21, 2022. THERE IS NO ENTRY FEE.

In addition to promoting the art of calligraphy, the Graceful Envelope Contest celebrates the role of letters in binding people together. The contest was created in 1995 by the Smithsonian Institution's National Postal Museum, which administered it until delegating responsibility to the Washington Calligraphers Guild in 2001. From 2003 to 2018 the National Association of Letter Carriers partnered with the Washington Calligraphers Guild.

Contest Rules
(Below: 2019 Best in Show by Christy Robb. Theme: Put Your Stamp On It)

2019 WinnersWHO CAN ENTER

  • Entries will be judged in these divisions:
    — Adult
    — Grades 9-12
    — Grades 5-8
    — Grades 1-4
  • Only one entry allowed per person.


  • There is no entry fee.
  • Each entry must be a stamped envelope, either manufactured or handmade, delivered through the U.S. Postal Service. The envelope will not be opened.
  • Entries may not be enclosed in a separate envelope or in any protective covering (unless multiple entries are coming from one class).
  • Postage of 58 cents applies to envelopes not exceeding 7x9 inches. Standard #10 business envelopes are also permitted, as are square envelopes--but square requires 88 cents in postage.
    Use calligraphy or hand-drawn artistic lettering to address the FRONT of the envelope/entry to:
    The Graceful Envelope
    P.O. Box 3688
    Merrifield, VA 22116

  • On the BACK of the envelope, print your name, address and email, clearly labeled "FROM." Students must indicate their GRADE (international students: please provide your age). (Students may use their teacher's email rather than their own.)
  • If your entry is returned to sender, contact Erin Cassidy, contest coordinator. All mail is sorted by machines, which can sometimes misread calligraphy.


  • Creative interpretation of the contest theme to transform an ordinary envelope into a work of art.
  • Quality of calligraphy or artistic lettering used to address the envelope. Computer-generated or -enhanced lettering is not permitted.
  • Effective use of color and design employing standard media such as paint, ink, markers and pencil. Not permitted: stickers or manufactured rubber stamps (hand-cut stamps and commercialy fabricated rubber stamps from a hand-rendered design are permitted).
  • Entrants are encouraged to integrate postage stamp(s) into the design.
  • See below for the advice of a past judge.


  • The Call for Entries and theme are announced in the fall.
  • Entries must be postmarked no later than March 21, 2022. The contest will not acknowledge receipt of entries.
  • *Judging will take place in Spring 2022 by three professionals from the calligraphic and arts communities. Only the front of the envelope will be judged (blind judging); the name, address and email of the entrant must be written clearly on the back. (If a class project, teachers should put their address and email on the back of each student's envelope.)
  • Winners will receive certificates and their names and entries will be posted online. No ptizes will be awarded. Please note: Entries not selected by the judges will not be notified, displayed or returned.
  • All winning envelopes can be viewed online at Adult winning envelopes will be displayed at Penny Post, a stationery and lettering arts shop in Old Town Alexandria, VA. Winners may also be published or exhibited elsewhere.


  • If you have any questions about entering or if your entry is returned to you, contact Erin Cassidy, contest coordinator.
  • To help the envelope reach its destination, make certain the zip code (22116) is easily readable.
  • First-class postage is 58 cents for envelopes weighing up to one ounce. Postage for square, oversized or unusual envelopes starts at 88 cents. You can use stamps issued in any year. NOTE: If you reside outside the US, use your country's postage in the denomination required for mail going to the States.

  • One of the judges of the 2011 contest, Shane Perry, provided this insight into the judging process:

    For the Graceful Envelope Contest, I look at a compelling design that grabs my attention and that conveys the theme, either directly or indirectly if it is cleverly done. The lettering needs to be well-executed and congruent to the overall design. Also, the use of the stamp needs to be well-considered, since it is part of the envelope, and therefore is part of the design. Envelopes that are expertly painted and/or drawn but contain lettering that seems like an afterthought would not be considered a winner. Expert lettering that does not produce a pleasing overall design that adheres to the theme would not be considered a winner.

    But an envelope with a design portraying the theme in a unique way, setting it apart from the pack, with lettering that works well with the design and a stamp that looks like it belongs, would definitely be in the running.

    Overall, I don't believe it is the best calligrapher that will always win, nor the best draftsman or painter — it is the artist who is able to use both effectively to execute the theme in the most compelling way

Themes of Past Contests

1995 — no theme
1996 — Mother's Day or stamp-related
1997 — Pushing the Envelope
1998 — National Postal Museum's 5th Anniversary
1999 — The Beauty in Nature
2000 — Significant Events from the Past Century
2001 — 25th Anniversary of the Washington Calligraphers Guild
OR Celebrating 200 years of Washington as the Nation's Capital
2002 — Greetings from America
2003 — The Written Word
2004 — The Weather
2005 — the letter P
2006 — A Fine Line
2007 — A Mailable Feast
2008 — C's the Day
2009 — Address the Environment
2010 — A Stream of Letters
2011 — Time Flies
2012 — D-liver D-letter D-sooner D-better (the letter D)
2013 — A World of Change
2014 — The Superlative Letter S
2015 — There's No Place Like Home
2016 — Communication
2017 — Pushing the Envelope
2018 — Whatever the Weather
2019 — Put Your Stamp On It
2020/2021 — Double Vision
2022 -- Greetings & Salutations