Guy Style // Man On The Go

May 16, 2016

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Mr. Pepper here! It’s been a while, but I’m back with some Guy Style tips to send over to your favorite dude…

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Lately, it feels like I’ve been living out of a suitcase and the airport seats have become my gate-side desk. I’m not quite as well-versed as George Clooney from ‘Up In The Air,” but I HAVE started to appreciate a few handy systems to make my schedule feel like less of a drag.

The strategy involved with many travel rewards programs can make earning points feel a little like playing a game, and so today I’m sharing a few tips and inviting you to play along…

1. It’s best to stay loyal, but don’t be afraid to shop around.

Most travelers will tell you the first rule of travel is pick a brand and stick with it. With brand elite status being such a coveted and valuable reward, it makes sense to focus your reward earning in one place. But what about when your airline doesn’t fly direct to your destination or your preferred hotel doesn’t have a branch in a certain city?  Thankfully, you don’t have to start all over from scratch and be treated like the rest of the status-less peons.  Most brands offer some sort of status match or challenge to woo you away from your competitors, and I’m not ashamed to use them.  Based on my status with Southwest (which I focused on earning first), I’m now also Mosaic with JetBlue.  Once I reached the Platinum level at SPG, I was able to also qualify for Diamond level with Hilton.  These status match offers are often targeted, but don’t be afraid to speak with a representative directly if needed, and simply ask what they might be able to offer in return for your business.

2.) TSA PreCheck is the best $85 you’ll ever spend.

Last Fall, Jessie and I took 2 hours out of our day to go sit in a boring office and tell someone that we should be trusted to fly without stripping down to our skivvies.  Now, the days of taking off my shoes, unpacking my laptop, and finding quart sized baggies that won’t rip when I put all my liquids in them are long gone!  (Like magic.)  A small investment upfront has already paid off in huge dividends, and the benefits will continue this Summer as we’ve been warned that security lines could get scary long. The best part is TSA PreCheck lasts for 5 years, so while the security-line process gets more and more ridiculous, I’ll be setting my alarm a little later and arriving to the airport just in time to walk onto my flight.

3.) There is always a shortcut to earning more points.

Stumble into a conversation with a frequent traveler and suddenly you’ll find yourself hearing about points, miles, and free upgrades. (I’ll admit it can sometimes be more than just a little annoying.) Thankfully, I really only have one thing to say about earning points:  There is always a quick way to earn more. My favorite (and most rewarding) tip is to encourage you to take advantage of Southwest’s credit card partnership with Chase when they offer 50,000 points for opening a new card, and then spending $2,000 in the first 3 months.  If you stack this offer with their business card under the same promotion, you’ll be well on your way to the incredibly rewarding “Companion Pass” that allows for your designated “companion” to fly with you for free wherever you go.  (Bonus point if you happen to have one as cute as mine.)

It’s a little funny to think that I’ve turned into the guy who pays attention to all of this stuff, but like I said: if it makes your trips feel more enjoyable and less like a chore, you can count me in. Jessie and I recently chatted about a handful of other travel tips that we use on the regs, and the next time you hop on a plane, train or automobile, I’d highly recommend tuning in to our lively conversations right over here!

In the meantime, let us know if you have any other great tips in the comments below, and until next time – Happy Travels!

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Get The Look:
2-tone gingham shirt from Nordstrom
J. Crew 484 broken in chinos + classic brown belt
Bloomingdales suede penny loafers (via Crossroads)
Warby Parker “Winston” sunglasses
No-show socks from Socks 101
Vessel pebbled backpack + rolling carryon (now on sale!)
Photos by Christa Norman

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