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The Five Questions: Jenn Gillespie

I absolutely love Pinterest — in fact, I don’t allow myself to visit before noon, otherwise my daily to-do list just doesn’t get done — but it remains a bit of a mystery to me. What makes one pin get repinned thousands of times — while an equally attractive one gathers dust?

I have been scratching my head over just this question, exemplified by the popularity of a gorgeous image from Calligraphy by Jennifer that I innocuously pinned some months back onto one of my boards, The Envelope. That humble yet gorgeous raven black envelope — interestingly enough, not even for a wedding invitation — became the subject of my Letter from The Editor in the winter issue of Stationery Trends, that, with any luck, will be hitting your mailbox very very soon. At the time I wrote the letter in mid-December, the image had been repinned 372 times and liked 43 times, but as of yesterday it’s been repinned 500 times and liked 58 times.

Pinterest is full of arresting calligraphy — and since it tends to be done on request by individuals as opposed to wholesaled by companies, I haven’t had much of a chance to cover it within the pages of Stationery Trends. In my opinion, Jenn Gillespie, the talent behind Calligraphy by Jennifer, is one of the best scrolling out there today.

Clients have included Mario Lopez and Ameriie, and getting blog coverage here is but one small jewel in a gem-encrusted crown, as she and her amazing output have appeared in many. It’s not hard to see why — her work is both distinctive and versatile, not an easy line to walk — and very of our time. In short: This is not your grandmother’s calligraphy!



dddJennifer very graciously answered my Five Questions during what I’m sure is one of her craziest times of the year.


1. SS: How did you get into this crazy business?

JG: I actually got into weddings after my own wedding!  I had a calligrapher do my wedding envelopes and thought how neat of an idea it would be to turn it into a business. I have always loved lettering beforehand but never knew I had the skill in me to actually produce work people would buy!  It took a lot of practice, patience, along with trial and plenty of error before I felt truly comfortable to share my work with people around the world.  Even to this day I am learning and still get inspired by seeing other calligraphers’ work.

2. SS: Are there any design or lifestyle trends you are finding yourself particularly intrigued with these days?

JG: I’m not sure this is a trend but I find myself fascinated with the extreme use of social media and all the amazing results it can have on ones business. Yes, it has been around for some time but it seems as though it has become a necessity for a business owner!  I mean who doesn’t have Facebook, Twitter, Pinterest and even Instagram now!  It’s one of the best things I’ve embarked on for my business, and while it takes time and effort, it’s so worth it and fun!

3. SS: What letter, card or invitation first comes to mind as the best you’ve ever received?

JG: Red Bliss Invitation Design sent me the most gorgeous laser cut Valentine’s card last year!  I actually display it in my living room because it is so pretty!

4. SS: What are your three favorite stationery lines?

JG: I love Bella Figura specifically because they outsource a lot of their work to calligraphers, and to me nothing beats a hand-lettered invitation:)

I also adore Ceci New York … she has the most intricate and beautiful designs I’ve seen!

Lehr & Black is also a favorite. These are such elaborate designs that nobody else seems to do.

5. SS: Is there anything you do personally to keep letter-writing, card-sending and invitation using alive?

JG: Hmm … well I do it everyday for a living — does that count? 🙂


Special thanks to Dragonfly Designs for sharing the first card shown on this post — the calligraphy is Jenn’s, but the fantastic design is all theirs!