Ask A Woman: Dressing for a big airport Pickup
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I live in Florida and next week a bunch of us are going to a beach rental house for the weekend. This girl that I’ve had a crush on for a while is flying into town (she lives in New Hampshire), and I’ve gotten the privilege to pick her up at the airport. From there I’m surprising her with a trip to her favorite Florida Restaurant, and then we’re heading straight to the island.
Obviously typically beachwear is in order for the weekend but how should I show up at the airport? I want to impress her but, we’re not going out on the town. Instead we’ll be eventually driving to a boat to head off to a beach island get-away? I was thinking boat shoes, jeans, and a t-shirt. What do you think?
Thanks for writing in–sounds like you have a great opportunity to move things along with your crush. So, let’s get right down to business. I LOVE boat shoes on guys. For the guys out there wondering what we’re talking about, boat shoes are quite similar to loafers, but usually come in more daring colors. Check out the wide variety of cool color combos for the Sebago Spinnaker. (I like the navy/white/light blue and the navy/white/tan combos). Definitely a preppy, clean-cut look. They look good and are comfortable so they’re a great alternative to sneakers. Wear them without socks.
Okay, back to Jared. Yes, wear the boat shoes. Jeans are great, too, but make sure they are well-fitting, in good condition, and on-trend. Now we arrive at the t-shirt. The t-shirt–in all situations, not just this one–is a make-or-break endeavor. When you say t-shirt, you might mean a tailored, high thread-count cotton garment, colored with organic dyes, which you painstakingly hand-wash and only line dry. You might mean an irreverent ringer t-shirt you bought after a brewery tour and too many free IPA samples, convinced the $39.99 price tag was worth it, until you peered at the brewery’s blurry logo in the head-pounding morning light. Or, it could be your old high school track t-shirt, pitted out and frayed at the edges, the plastic text peeling away from the faded cloth, a monument to your faded 4×4 relay glory.
I like t-shirts as much as the next guy. They’re comfy; they’re roomy; they breathe–what’s not to like? BUT, when dressing to impress, be CHOOSY. The t-shirt should fit well: if you are rounder in the middle, it should not be so tight as to create horizontal creases across the tummy. The t-shirt should be in good condition: NO pit stains, holes, or grease smudges. The t-shirt should have an appropriate “theme”: no sayings about how much tequila you drank last night, how many women you’ve slept with, or the NASCAR logo. Still unsure whether your shirt will make your date enamored or nauseous? Tell me this–where do you keep it? Folded neatly in the same drawer with your polo shirts? Or crammed into the corner of your closet on a pile with your workout shorts? If it’s the former, go for it. If it’s the latter, choose something else.
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