Chris Black’s Favorite Sumer Basics: Shorts, Shirts, & Hats

Chris Black (a partner at brand consultancy Public Announcement) answers our most pressing taste-based questions; if you have one, email [email protected] with the subject line “Ask Chris.”

If you’re looking for the most powerful hair dryer or the handiest chef’s knife, those things can be easy enough to find. Other objects of desire are a little more taste-based. What’s the next status water bottle or handwash, for instance? If you have a burning question about the next fanny pack or Noah rugby shirt, Chris Black is here to answer it in a regular column.

I have cultivated what I think is the perfect look for warmer months. I playfully refer to it as Ivy Sport™️, even though I, uh, did not go to college. The term was coined by my dear friend Jake Davis a few years ago, when he was describing my post-tennis dress. It’s basically a combination of casual, comfortable, and (mostly) affordable technical gear and preppy staples that, somehow, just works. (Even my mom likes it.) Taking something buttoned up and a little boring and making it your own is what personal style is all about.

Below, I’ve listed my go-to options and a few pieces I might add to my rotation for the look’s main components — shorts, shirts, shoes, and hats. I’ve also included an (optional) fifth component, sunglasses, because we all know that sometimes accessories can make the outfit.

It starts with shorts. As I’ve said before, a five-inch inseam is my preferred length. You’ve got to let the quads breathe. This classic Nike pair is my go-to. Well-ventilated, lined, and they even have pockets.

Another go-to are the oft-discussed Patagonia Baggies. They come in wild colors and prints, but I prefer mine in black — and with a five-inch inseam (there is a longer seven-inch style as well). The roomy pockets take some getting used to, but can hold everything easily.

Jacques is a brand that has recently come onto my radar. The young company, which debuted in 2018, bills itself as “an elevated men’s performance line” and these shorts definitely speak to that. Unlike the two pairs above, they’re logo-free — a minimalist touch that lends them a level of sophistication. But like the two pairs above, they are designed with performance in mind and feature four-way stretch fabric, a water-repellant outer, and a moisture-wicking interior. Note that they only have a back pocket, so you might need a tote bag if you’re planning to wear them on a longer excursion.

A logo-free polo shirt is essential to my summer wardrobe. I like these, from Uniqlo — an unfussy, excellent fit, and they age well. I buy three at a time and recommend it in navy, though there is no shortage of color options.

A blue oxford is the cornerstone of my wardrobe, even in the summer. The style, to me, is seasonless: It can be worn with the sleeves rolled up, over a T-shirt, or properly buttoned. Again, Uniqlo makes a terrific one for the price — I have said before how I still wear a beat-up, light-blue Uniqlo oxford that I’ve had for close to a decade.

If you’re looking for a fancier option, this 100-percent cotton version from small New York City–based brand Corridor is excellent. (Washing and drying will help to age and soften it.)

For those chilly nights, a classic cricket sweater from Ralph Lauren can be thrown over the shoulders. Alone it may be full turbo prep, but styling it with the more athletic-oriented pieces will dial that aesthetic down. And in the fall (or spring), once temperatures start to drop and stay there, it can be worn as a layering piece.

A loafer is my go-to summer shoe and my favorite loafers are Bass Weejuns. I own this pair, with tassels, which is slightly more festive — but I also own this non-tasseled pair, which is simpler.

For something even wilder, Bass has collaborated with legendary British brand Fred Perry on a pair of Weejuns with a chunkier sole that comes in black, bottle green, navy, and oxblood (sizes for all are limited, so if you see a pair in yours that you like, you might want to scoop them up).

When it comes to more casual footwear, quoting myself, these are “the perfect summer shoe — understated, durable, eternally cool.” I wear them sockless.

For a little bit more money, Vans sells some similar-looking (but less ubiquitous) pairs of Vault Authentic OG LX shoes that come in lace-up and slip-on varieties. They’re a bit sturdier in terms of construction, but also harder to find (sizing is limited in both styles right now).

I typically rely on hats to protect my eyes and face from the sun when it is blazing and I am outside. Nike’s Featherlight cap is my go-to — it’s affordable, breathable, and straightforward. Any color works!

Less technical than the Nike hat (for those who don’t want to go full Dri-Fit) is the New York Times’s iconic logo hat, which the publication calls no less than the “common man’s crown.” I like it in this fresh navy and white, but it’s also available in black and white.

If you want to freak it and protect it (the latter it being your dome), I suggest Montbell’s breathable mesh crusher hat. I will admit it may be too advanced for this lowly style arbiter, but if done right, this could really take a fit to the next level.

Sometimes, a hat alone will not shield your eyes from the sun and you will need some shades. These, a collaboration between Noah and Vuarnet, are sophisticated but sporty and could be worn on the tennis court or while jogging. Durable tortoise shell, 100-percent UV protection, made in France. In other words: Can’t go wrong.

Feeling fun? This transparent square-shaped pair from Sun Buddies, in an appealing shade called “rose water,” will look great with any of the otherwise understated shorts, shirts, hats, and shoes I’ve mentioned above.

Maybe you want something classic to protect your peepers. In that case, you can’t go wrong with this simple black Persol pair that has subtle green lenses. Handmade in Italy, they are eternally wearable, and the tint gives them just enough kick.

By submitting your email, you agree to our Terms and Privacy Notice and to receive email correspondence from us.

The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.