Strangely, it isn't always the big dates, garden casual weddings, or job interviews that are the most annoying events to figure out what to wear. Sometimes, knowing how to dress better than a baggy T-shirt and shorts without erring on dressing up for something like a weekend matinee with your family in the middle of summer presents a unique problem.
It's important too – not only are you spending time with your kids, but this weekend afternoon outing also serves as a day-date with your spouse. One personal measure of good style is looking intentional and appropriate for where you're going.
What we're going for: Casual but style-conscious dad vibes

A Lightweight, Textured Polo
The polo is standard issue uniform for a majority of guys who are trying to not wear a t-shirt but don't want a button up shirt.
They also have a tendency to look kind of junky because cheap and/or old ones begin to curl at the collar. And, unfortunately, unlike some men's staples like a leather jacket, polos don't look better the older and more beat up they get.
One way of tackling that and adding some interest to an otherwise mundane shirt style is to choose one made of a non-pique cotton (the material most polos are made of). For cooler weather a knit, almost sweater-like option is sharp and vintage, but for super hot days of summer I like to keep it light with a slub cotton or linen-cotton blend.
Slub cotton is a type of fabric characterized by its uneven, textured appearance, created by weaving cotton with slight knots and imperfections.
A Light Jacket for Movie Theaters & Other AC Blasting Summer Spots
The weird part about the modern air conditioned world is in summer we often feel like we need a jacket only to wear inside.
Enter the Harrington jacket, the perfect solution for navigating those icy movie theaters and frigid restaurants.
The advantage of a lightweight jacket like this is not because it's light to wear, but because it's painless to carry. Bunch, it roll it, throw it – it'll still look great when you put it on.
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Straight Fit Jeans
My first foray back into non-slim jeans several years ago was the original, Levi's 501. When I first put them on I couldn't get over how loose they seemed compared to what I was used to wearing.
But after they got through a wash and a few wears, they draped much more naturally, and quickly made me feel that many of the slim jeans I had were noticeably too restricting.
Penny Loafers
Penny loafers have a storied history, originating in the 1930s. Initially designed by G.H. Bass, these shoes feature a distinctive strap across the top, where teenagers eventually started placing pennies – hence the name “penny loafer.”
Today, penny loafers remain an enduring choice for those seeking a blend of history and effortless style. They pair easily with anything from shorts to jeans to chinos to dress pants.
→ Read more: A Lesson in Buy Once, Cry Once>