One family. Six personalities. Very little agreement on what constitutes a good-looking shoe.
Buying for family should be easy. You already know these people: what they wear, what they complain about, what they order for dinner and which opinions they will defend long after everyone else has moved on.
Yet gift giving has a way of exposing how often we confuse knowing someone with assuming they should like what we like.
We start in Chicago, represented here by the Chicago Skyline Court Sneakers, where this family is from, and where strong opinions about architecture, sports, pizza and apparently sneakers come with the territory.
We started with one Midwest family we know particularly well. Their sneaker choices included an American flag, Mondrian-inspired geometry, paisley, multicolor prisms and bright painterly brushstrokes.
There was no family aesthetic.
That was encouraging.
Don’t correct their taste
The patriarch of this family chose, naturally, the USA Flag Court Sneakers.

They are stars-and-stripes sneakers. Not a tasteful little flag hidden near the heel. Not navy with a discreet patriotic reference. Actual stars. Actual stripes.
There is a type of gift giver who sees this and immediately starts editing.
Could we tone it down?
You could. You would also be missing the point.
A good gift does not need to meet in the middle between your taste and theirs. Sometimes knowing someone well means knowing that subtlety would make the gift worse.
The American Flag Sneakers in the wild. As in, the suburbs.
The same rule applies in the opposite direction.
The adult son, a gentle yet indecisive Libra went for the Multicolor Prism Sneakers, a riot of pink, orange, blue, yellow and purple geometry. We have photographic evidence that these did not disappear into the back of a closet after Christmas.
Some people should not be given beige.
Versatility is useful when buying an office chair. It is not always the highest calling of a gift.
Another American classic, the ever versatile, every-color sneaker, Multicolor Prisms in the wild. As on artificial turf in the city.
Personal doesn’t have to mean sentimental
Personalized gifts have become heavily dependent on initials.
Initials on tote bags. Names on tumblers. Important dates in cursive. Coordinates of somewhere meaningful.
All perfectly nice.
But knowing someone's initials is not quite the same thing as knowing their taste.
The mother in this family, who keeps track of birthdays, anniversaries, weddings, new grandchildren and sale prices with near-geometrical precision, was given mostly white Mondrian-inspired sneakers punctuated with red, blue and yellow blocks, reminiscent of the calendar squares she is so fond of.
The Mondrian Style Sport Shoes, feel like perfectly stacked squares, ready for daily errands or travel adventures with the tidy certainty of a Euclidean axiom.
Her daughter, the eldest child, the typical popular kid who excels at nearly everything in life, went in a different direction, yet never far from making the right choice, with an intricate blue-and-peach Paisley Court Sneaker, that can’t go wrong no matter what the day brings.

Neither pair announces who the recipient is.
They simply look like something that particular person would choose.
There is something more intimate about getting that right.
Not every personal gift needs to explain why it is personal.
And not every attractive thing requires a touching backstory. Sometimes someone likes paisley.
Let her have paisley.
The Paisley Sneakers: Paisley Pattern Court Sneakers becoming, intentionally or not, the star player at a mid-June lacrosse game.
Let children choose with their eyes
The granddaughter chose Brush Stroke Court Sneakers, splashed with bright pink, orange and yellow paint.
She liked painting at the time, which may explain the choice.
It is equally possible that Grandma was paying and she saw something colorful she liked.
Brush Sneakers: Brushstroke Pattern Court Sneakers. It could be art. It could be someone who couldn’t decide what color to paint the newly renovated kitchen.
Children are refreshingly bad at overthinking gifts. They do not ask whether something is timeless, whether the color will transition between seasons or whether a safer option might get more wear.
They like it.
Decision made.
Adults occasionally turn personalization into a test of how profoundly they understand another person.
Delight is also a perfectly good reason.
Don’t overlook the obvious
There is one more member of this family to shop for: the veteran college swim coach. Otherwise known as the dad who keeps everything together, with the seemingly effortless efficiency of a well-executed relay.

We could study his wardrobe. Investigate his other hobbies. Attempt to discover an interest nobody else has noticed. Or not.
We could simply give the swim coach the Swimmer Illustration Court Sneakers.
Gift guides tend to treat the obvious choice with suspicion. If the answer comes too quickly, perhaps it is not thoughtful enough.
Sometimes the opposite is true.
The obvious answer is obvious because you have been paying attention.
Swimming Sneakers: Swimmer Illustration Court Sneakers, up close: essentially a tiny pool in sneaker form.
This is the first in our regional family gift-guide series.
Next up: another part of the country, another family, and an entirely different definition of good taste.







