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  • Writer's pictureEvan Wolkenstein

Why you should wear a tie on vacation

Relaxing vs. Letting Go

When I leave work, stressed out and exhausted, I have two options, and I usually do the wrong one.

I can come home, take off my teacher-costume, and lay on the carpet, watching cats on Youtube —  or I can go to a cafe, read for an hour, draw in my journal, blog, and then go home.

When I do the first option, time passes, but I never really feel more relaxed. My evening quickly turns into an ongoing quest to feel relaxed. In some sense, I never really get off the floor.

When I do the second option, an hour passes, and I arrive home with the work day squarely behind me. I no longer need to unwind. I’m “unwound.”

This is because “relaxing” and “letting go” are not the same thing. “Letting it go” creates a new hunger: to continue “letting it go.”

On vacation, many people tend to dress in what they think of as “relaxed” clothing. Understandable. Making it through the semester, the 2nd quarter, the fiscal year, the project – it nearly killed you – and it’s time to relax.

But the same psychology applies – we’re temped to slip into the most “relaxed” thing we can find to wear, and spend the day – the weekend, the vacation, whatever – in shorts, flipflops, t-shirts, and the like: on the beach, in the vacation house, around the hotel, at a restaurant.

And truth is, there’s nothing wrong with any of these clothes, if you love wearing them. But if you’re only wearing them on vacation because that’s the most relaxed thing you own – and you desperately need to relax – you may not be doing yourself a service.

You may not actually feel more relaxed as a result, and the little extra bit of attention you would have gotten for dressing on point? It’ll go to someone not wearing board-shorts and a tank top.

Dressing relaxed vs. Like a slob. No offense.

Now, don't these folks look relaxed? "Beach vacation? Capitol idea!"

Now, don’t these folks look relaxed? “Beach vacation? Capitol idea!”

I propose rolling back the clock a little, and thinking about what people wore on vacation – you know – back in the day. You’ve seen the sepia pictures. Men on vacation might have worn a tropic-weight suit. A linen shirt. A straw dress-hat. Women might have worn a festive dress. Capris and espadrilles. Colorful prints.

linen suit

“When I go on vacation, I’m careful to lean jauntily against every lamp-post I can find.”

Tonight, on the other hand, in one of the finest restaurants in Santa Barbara, I saw men and women dressed just like that. For an elegant, relaxing evening in a beautiful place. One table over, others dressed as if they’d just rolled out of bed.

Neither is more correct. But I’d like to suggest: it might not be as fun (or relaxing) to wear a t-shirt and flip flops to a restaurant as it is to wear something really snazzy. Not something that says, “I’m trying to relax” – but rather, something that makes you feel awesome.

Think of vacation not as a time to let it all go – but rather, as special time. It’s time you deserve. Dress up for it.

How to about dress relaxed – and yet styley.

Beach Bro. Love it? Wear it. But I have some other ideas for you.

Beach Bro Couture. You love it? So, wear it. But I have some other ideas for you.

If you step on the plane to Vacation-land and automatically slip on the beach-bro gear, maybe it’s because you love it and well, you should keep wearing it. But when it comes down to it, there is nothing inherently “authentic” about this stuff. It’s the most commonly peddled gear along every boardwalk. It’s the most common look. But it doesn’t need to be your look.

1. Wear bright, primary colors and bold stripes 

This is the fastest and most forgiving way to step into styley vacation-gear, and to step out of the throngs of board-shorts and tank-tops. Wear blue, red, and white. Yes, like the American Flag. No, you will not look like a flag.

Recognizable color scheme... but does not appear that Betsy Ross dressed me.

Patriotic color scheme… and yet, it does not appear that Betsy Ross dressed me.

nautical stripes

You seriously cannot go wrong with nautical stripes.

Here it is. A comfy fabric. A beautiful color. And nautical stripes look great on everyone.

Here it is. A comfy fabric. A beautiful color. And nautical stripes look great on everyone. Club Monaco nails it.

2. If wearing pastels and linen, be sure it fits perfectly. 

Otherwise, you will look like Uncle Russ on vacation. Or like the guy in a Lipitor ad.

Check to make sure the shoulder seams hit your shoulders (see my diagram),

Not too high. Not too low. Makes your shoulders stand up and say "wassup."

Not too high. Not too low. Makes your shoulders stand up and say “wassup.”

and that nothing is too baggy. If this is freaking you out, go back to #1.

3. What you wear on the beach should not be what you wear in a restaurant, at a bar, or to a party. Unless they happen to be on the beach.

American style sometimes confuses “sportswear” with “sports gear.” What’s the difference? Think about it: what is a sport-coat? It’s a less formal jacket that men wear when they’re not in a business meeting. It can be worn out for dinner, to a party, to a show. “Sport,” in that context, means, well, “not formal.”

You do not play beach-volleyball in your sport-coat.

Vice versa is also true. Whatever gear you wear to play sports, or to look like you’ve been playing a sport, doesn’t need to go with you to your evening plans .

Look at what Don wears to the beach (left)…and what he wears when he sips a drink /contemplates the pieces of his broken life (right).

Mad Men (Season 6)

Don’t imitate the “drinking away your emotions” thing, but this approach to dressing for vacation is on point.

don bathing

I don’t think it’s a good idea to read Dante on the beach, but if you’re going to, try wearing a classic-color bathing suit instead of a high-tech, neon orange pair of board shorts.

This guy is probably on the right track, but with his shirt hanging out, it's hard to tell.

This guy is probably on the right track, but with his shirt hanging out, it’s hard to tell.

4. Tuck in your button-up shirts. 

If your shirt is slim-fitting, sure, wear it out. But try tucking it in, first. You might like what you see. And if it’s not slim fitting, definitely tuck it in.

5. Polo shirts

Baggy, tucked in, with cargo shorts? No.

Baggy, tucked in, with cargo shorts? No.

When wearing a polo, it must be slim. Stick to blue and black, and pair it with well-tailored pants.

When wearing a polo, it must be slim. Stick to blue and black, and pair it with well-tailored pants.

A polo shirt looks great with a few caveats. It cannot be baggy. If you must wear a polo, wear black or dark blue, and consider tucking it in. Notice the difference between Uncle Russ in his favorite polo, and the guy on the right, who looks suspiciously like a certain ad exec from the 60s.

Notice how sharp a polo can be when it’s slim fitting and tucked in. This is not the same as a baggy polo over kakhi shorts with socks pulled up. Save that look for when you’re retired.

6. Wear a tie 

Portrait of the artist as deeply, deeply relaxed. (And the wine was awesome.)

Portrait of the artist as deeply, deeply relaxed. (And the wine was awesome.)

You were wondering when I was going to get around to this.

I’m not talking about the tie a banker wears, or the tie a geometry teacher wears. I’m talking about the kind of tie a classy, stylish guy wears on vacation.

It should be skinny, it should be made of a light material like linen or cotton, and it should have a fun print.

Two companies that nail this are the Hill-side and General Knot & Co. They often incorporatie vintage, salvaged cloth into their fresh designs. Pair one of these with a slim-fitting, white shirt, and you’re golden.

(In fact, there’s a huge sale at the Hill-side, until June 29. Pick of the litter, a “beach tie” made from gorgeous cloth for less than a mass-produced tie from a big-box store).

Wear a tie on vacation. Maybe you’ll get a better seat in a restaurant. Maybe the clerk will upgrade your suite. Maybe the flight attendant will give you an extra packet of peanuts. I can’t guarantee any of that, but this I know from personal experience: you will feel great. And to circle back to the theme of this post, you will enter into a state of mind where you are right where you need to be – relaxed, deeply in your element.

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 What to avoid

Now that we’ve covered some basics, here are some suggestions about what to avoid altogether.

1. Avoid clothing that advertises absolutely any sports gear, vacation destination, or tropical kitch. That means no advertising for Señor FrogsBody-Glove, or Billabong. Even if you have been there or use their gear. That also means no Bob Marley shirts. Feel free to enjoy surfing, reggae, whatever floats your boat. Don’t walk around as a billboard, saying, “I’m a mellow surfer guy. I’m a party dude.”

If you are one, just be one.

What happens if it's too big and too loud.

What happens if it’s too big and too loud.

Yes, I know. It's Elvis. But you'd look good in this one, too.

Yes, I know. It’s Elvis. But you’d look good in this one, too.

2. If you have a hankering to  wear a Hawaiian or tropical print shirt, the pattern should be in tasteful colors. The cut should be slim. Look at the difference between the classy shirt that Mr. Presley is wearing, compared to these too-big, too-loud, see-em-all-the-time specimens.

3. Fleece and other “adventure-gear.” This goes along with saving beach-gear for the beach. Save your fleece vest and pants-with-lotso-pockets for your nature hike.

4. Lastly – and this is what it all comes down to: wear a Bob Marley fleece tank-top with your socks pulled up and binoculars around your neck if you want to – but under no circumstancesever, should you boss a waiter or waitress around, snap your fingers for a bartender, rage at the airline attendant, or subject the people around you to your drunken bellicosity or bonhomie. There is nothing stylish, whatsoever, about that guy. 

No matter what he’s wearing.


If you enjoyed this, check it the first entry in the “Why You Should Wear A Tie” series, “Why you should wear a tie to the park.”


And…a contest for my readers!

Send a picture of you on vacation — at your most stylish — to StyleForDorks (@) gmail (dot) com. I’ll share a few of the best  next week!

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