Ask A Woman: Dressing for a big airport Pickup
If you’ve got a question that needs the female treatment, chances are you’re not the only one who wants to ask it. Beth is our source for the answers. From opinions on men’s style to decoding the sometimes mysterious ways of women, she’ll take on a different question every Thursday. And don’t worry, your identity will be protected too. Click here to get to know Beth, then get in touch with her by sending your question to: askawoman@dappered.com
—
.
Beth,
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?
– Jared
—
.
Hi Jared,
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
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.
– Beth
.
Got a question for Beth? Send them to: askawoman@dappered.com
I’m sorry Beth, but I’ve got to disagree with you here. First off, you only used one sentence to describe the jeans a guy should wear. It seems simple enough, but do you know how many guys are walking around in gaudy True Religions because they are “on trend”? Skip trends; go for a pair of Levi’s Shrink-to-fit 501s if you’re short on cash (around $35), or if you’ve got some money laying around, APC New Standards (around $155). They’re both classic, and can remain in your wardrobe forever. Next up is boat shoes. While the Sebago Spinnakers look decent, there really is only one choice when it comes to boat shoes: Sperry Topsiders. The originals are only $70, so do yourself a favor and get the real deal; at least you know what you’re getting quality wise, and everything about them is classic. Finally, do not wear a t-shirt. I don’t care if it’s a $100 organic cotton one-off designer tee make custom for you, it is not appropriate for a date (unless you’re in high school, in which case go for it). If you’re going for a casual look but still want to impress, I would go with a polo. I’d recommend a slim-fit Ralph Lauren (NOT the ones with the big pony on the front) or Lacoste, but any other polo (such as the American Eagle polo without the logo previously featured on the site) will do if it’s in good condition. Again, my apologies to Beth but I think this is the route to go if you really want to impress her.
What about a linen button-down w/ the sleeves rolled up halfway? It’s light enough for the beach, but a little classier than just the standard t-shirt. That, and/or pairing with khakis over the jeans? I mean, he’s looking to impress, and a t-shirt and jeans just doesn’t say that, in my opinion. Good luck though, either way!
@Patrick: By saying “there really is only one choice when it comes to boat shoes: Sperry Topsiders…” isn’t that like saying: “Although a fuji is tremendously tasty, there really only is one choice when it comes to apples. The Brabeurn.” C’mon Patrick. You could put “British Knights” on the tag for those black and brown ones, and I’d still want a pair. Those are sweet. Now, I think a polo is a good idea too (Target Mossimo! $8!), but also remember that this isn’t technically a date. Y’know? If she’s getting off the plane super casual ready for the Island, you don’t want to completely out dress her. Is there a danger there?
Sure, if you want to go with any old boat shoes, go ahead. However, in my mind the original is perfect in every way, and as Wikipedia states, “Modern boat shoes were invented in 1935 by Paul Sperry after noticing his dog’s ability to run easily over ice or snow.”. As the old adage goes, “if it ain’t broke, don’t fix it”, and it’s the same price why not just go for the real deal?
In regards to completely out dressing her, there are two main problems. First, do you dress for other people, or do you dress for yourself? Don’t worry about what she’s wearing (ESPECIALLY since this isn’t a date), just wear what is appropriate for the situation. This brings me to my second point: a polo is a very casual shirt to begin with, and is wildly appropriate for a relaxing island getaway. If you “completely out dress her” just by wearing a polo, what is she wearing in the first place? Ugg boots and a jean skirt?
@Patrick: I hope the girl Jared is meeting at the airport ain’t as particular as you Patrick 🙂 Imagine – (OhmyGod, he’s wearing Sebagos and not Sperrys? GET ME A TICKET BACK TO NEW HAMPSHIRE NOW!!!) As far as dressing for yourself or others, I agree that you should dress for yourself first. BUT… Funny thing about charm, is that you do in fact have to be concerned about how other people are feeling. Your job is to make them feel as comfortable/happy/engaged as possible. I agree that a polo won’t make her feel under-dressed, but, you do need to take that into consideration.
I think Beth’s point about the clothing being clean and neat is true of anything. If your clothes are clean, you’ve made a great first impression with any woman.
I’d probably opt for a short sleeve button up in this situation. I think it is not only classy, but it also shows you’re ready for the whole weekend.
I agree Patrick is being a bit particular. Are you saying you only wear the ORIGINAL maker of every type of clothing or shoes you own? That’s a bit rediculous. By that logic, you are lame unless your leather shoes look like.. this! Yes, a bit extreme hehe, but you get my point.
@Bryan. Did this when I saw your example.
No, I’m not saying you HAVE to wear the originals, but for the same price the originals look better and have a legacy attached to the brand. Same goes for Clarks Desert Boots, RW Williams Chelsea Boots, etc; if the original truly is the best, why go for anything else?
Hello Everyone!
This is the real Jared that originally wrote in. I just got back in town from our beach get-a-way! Let me tell you first that it was amazing. A private island just outside Boca Grande! And can’t forget the good company 😉
So what did I end up wearing….well — A pair of Sperry’s, chino’s from JCrew, and a comfy plain fitted grey t-shirt from Nordstroms. Kept it casual and light for the warm FL weather!
Thanks Beth for taking the time to reply and answer my question. Yes, she was impressed!