14 Warm-Weather Style Tips: Use Now, Repeat All Summer

Now's the time to get outside — but what shoes should you wear? And how about that hat? The Esquire fashion director is here to answer your sun-soaked questions.


I've been invited to a party with a purple theme. How can I dress without looking like the Joker?

Are you expected to wear only purple? If that's the case, feign illness and stay home. If not, wear a purple tie. That should help.


Can I wear boat shoes with socks?

Listen carefully and no one need get hurt. Step away from the Sperrys (which, by the way, should still be wintering in a bucket of frozen Northeastern seawater to add to their salty patina come spring) and buy some shoes that are actually meant to be worn with socks. Oh, and never put boat shoes and socks in the same sentence again — the best-dressed sailors always go bare ankle.

Biasion Studio/WireImage

Are some socks better suited for summer weather than others?

Excellent question. Massimiliano Bresciani's eponymous family firm, based in Bergamo, Italy, makes some of the world's best socks in a multitude of natural and sometimes obscure fibers like deer hair, and recommends the company's linen socks for summer. He tells us: "Linen is two to three times stronger than cotton, and it's smooth and lint free. It absorbs moisture easily without feeling wet, so it wicks perspiration away from your skin very well. It's a tough yarn that doesn't stretch."

Jeffrey Westbrook/Studio D

We bald men need protection from the sun. Could you give some recommendations?

Come, come: We are not against all hats, per se. Hats are fine. It's only when they are put on people's heads that they become problematic. Fifty years ago, not wearing a hat was a statement; today, wearing a hat is unavoidably a statement. That said, you're right that hats perform a valid function in summer. You might opt for a classic panama, a favorite of outdoorsmen like Teddy Roosevelt and famed aviator and Cartier muse Alberto Santos-Dumont. The panama, superlight and comfortable to wear in the stickiest weather, is perfect for wearing with a suit if you must wear a hat at all.

Courtesy of Wiki

What is the protocol for rolling up one's shirtsleeves?



I just bought two new suits, and my wife is insisting that I get rid of two older suits.

By removing the older suits, you will only ruin your new suits quicker because you'll wear them more often. This is not good economics. You know it makes sense. Now go convince her.

Martien Mulder

When wearing pants and a dress shirt, should my pants always be darker than my shirt?

As a rule of thumb, that's a pretty reliable one. You certainly want to avoid the black-shirt-white-pants thing; that's a bit Barry Manilow. Better to stick with lighter-colored shirts and darker pants, but this time of year, you don't want to go too dark. Stick with lighter blue or gray trousers.

Jeffrey Westbrook/Studio D

I have a "peekaboo" tie with a drawing of a pinup girl in the lining...

...My wife says the point is to keep it hidden. Is she right?

Your wife has a point. The mantra "Don't show off, impress" might be apt here. Such playful details are meant to entertain the wearer more than anyone else, so if you show it off too much, it loses its power.


I recently purchased a couple pairs of nice jeans, but they're all too long.

It's almost impossible to remake a bottom hem that has been rolled and stitched before (usually) being washed and abraded to give it that worn-in look. What you need is what is called a European hem — a good alterations tailor removes cloth from each leg and then reattaches the original finished hem so the join is barely visible. As for a tailor, get some local recommendations; a good test is to ask the tailor how he would tackle it. Ensure he knows that you want the original hem put back on. And finally, wash your new jeans before getting them altered, as shrinkage can occur in the wash.

Mike Stefanov

I'm looking to buy a classic leather jacket — something like a brown bomber. Any suggestions?

Ralph Lauren has the perfect update of the classic A-2 flying jacket in its spring collection. And Alpha Industries, which celebrated 50 years of its authentic government-issue flying jackets last year, has a replica version of the A-2. Try it.
Jeffrey Westbrook/Studio D

Can I wear my Coogi sweaters today, or do I need to move on?

May I suggest that you move on, and while you're at it, invest in a round of hypnosis to ensure they don't linger in your memory, either. The Coogi sweater, though once an immense success, is proof of the fashion mantra that the more in-your-face a garment is, the less often it gets to make a comeback. It is, accordingly, not scheduled for reappraisal until May 2072.

Courtesy of Coogi

Is there a name for the type of collar the main character on White Collar wears?

Yes. It's called a really bad collar. One that's too small for a grown man, too small to encompass a tie (which is why it has that over-stuffed-sausage look about it), and too small for the suit he wears with it. You can see what they're getting at with his outfits — a kind of modern Mad Men look — but the wardrobers on Mad Men know that their show's look is as much about proportion and fit as it is about skinny lapels. White Collar's look is all wrong. It's like someone stuck a skinny lapel on a sack suit (and a shirt) and called it stylish. The balance is off, the sleeves are too wide and the pants are too big.
Nigel Parry/USA Network

Do belts and shoes have to match?


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Are rubber-soled dress shoes more informal than leather-soled ones?

It's true that leather soles tend to be a bit more distinguished than rubber ones, but it's not a hard-and-fast rule. Some high-end brands specialize in dress shoes, and others, like Salvatore Ferragamo, offer rubber-soled options that are just as dressy as their leather-soled counterparts. The truth is that choosing leather or rubber is less about form and more about function. Rubber soles usually last longer, especially in rainy places, and some men bleat about leather soles being less comfortable than rubber ones. Mind you, these are probably the same men who would wear suit trousers with elastic waistbands, so take such complaints with a grain of salt.

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