This year we like to think we’ve really got your back—from gifts to buy, to what to wear, to how to make present wrapping not totally terrible. We’re sitting down with our team to glean a little pro advice to get you through the season with flying colors (blue being a nonnegotiable, of course). Next up is our friend Brian Kaspr. He’s an artist who has lent his talents to several of our leather goods, and if you haven’t had a chance to snag one of his monogrammed masterpieces, he’s making guest appearances during our Personalization Palooza in stores all season long (details below). Read on for his tips on how to give, arguably, the best gift ever: a one-of-a-kind monogrammed leather bag or accessory.

Getting something monogrammed is a bit like baking an apple pie: crowd pleasing, comforting, sweet (but not overwhelmingly so) and timeless. When gifting something monogrammed, however, you need confidence to take that leap of faith—you’re customizing what could be deemed an already great gift. But we, of course, strongly believe it’s worth it. Anything personalized just feels like it’s got “heirloom” written all over it (not literally but you get the idea), and could there be a better thing to strive for when deciding what to purchase for someone you love? Initials are a fail-safe choice, but these days some of the most interesting monograms feature nicknames, acronyms or words. To help you go forth and decide what exactly to say with that monogram, we chatted up Brian. He knows a thing (or 4,000) about how to make the call.

You’ve been making people’s clothes and accessories personal for a while now. What are the most commonly requested things?

Brian: People typically go for their nickname. This is often after a long internal discussion of whether their nickname is worthy of the accessory’s real estate. Second place is simply their first name. Everyone should have a go-to word or phrase for these situations. Mine is “Cry Cry Cry”—it’s weird and cryptic, also it was a common phrase of my grandfather’s and the name of all of his boats.

Wow. Love that. OK, the practical steps. Once you’ve picked the item to personalize, what sorts of questions do you ask yourself to figure out what the best monogram is?

Brian: Here are a few… Is this person quirky? Would they like an inside joke monogram? Do they already have stuff monogrammed? If so, what does that tell you? Would they want a word, rather than their name? Do they have a favorite book, object or food?

Any surprise-monogram-gifting success stories?

Brian: The most common surprise gifts are for weddings. Either brides surprising bridesmaids or vice versa. It’s always so lovely when someone gets something for themselves and something for a close friend, especially when the two play off each other, like nicknames that relate or a literary yin-yang situation. There was a set of friends I worked with both named Katie and both pieces said “The Other Katie.”

Any more examples of personalization you love?

Brian: I have a fascination with amateur drag race car names. They are all so weird and specific and some are not dragster-y at all, like “Pink Chablis.” That’s a real dragster. I have a photo to prove it.

Now in the spirit of your artwork and the one-word idea, we challenge you to answer these questions in one word (or at least very few).

Q: Describe the perfect holiday party.

Sparkling (or maybe luminous).

Q: If you could personalize one thing for yourself, what would it be?

A bar.

Q: A personal moment you definitely don’t want caught on camera.

Either singing/talking to myself in the car or how much I lick and bite my lips when working. Or maybe how I talk to my cats.

Q: A personal moment you love capturing on camera.

The creative process. It’s so hard to communicate.

Q: Your guilty pleasure.

There is no such thing as a guilty pleasure, but we can say Reese’s Peanut Butter Cups.

Thank you, Brian.

Want to hang out with Brian IRL (and pick up some monogrammed goodies while you’re at it)? He’s on-site at our stores in Washington, DC; Boston and New York City this month for the Personalization Palooza, hand painting complimentary monograms right on the spot. See full details (and RSVP) below. 


Saturday, December 3rd, 12–6pm
Sunday, December 4th
, 12–6pm


Saturday, December 10th, 12–6pm
Sunday, December 11th
, 12–6pm


Saturday, December 17th, 12–6pm
Sunday, December 18th
, 12–6pm