Humor Me: Choosing the Right Shoes for a First Date

Hello, everyone! Today we’re introducing a new column, HUMOR ME, written by Sarah Solomon. Sarah’s going to be offering advice and sharing observations on men’s style from a female perspective – all tailored with her irreverent brand of wit with a chaser of sarcasm.

Fashion and style don’t always have to be so freaking serious. So let’s lighten up. Please give her a warm welcome! – HSS

If a guy has good taste in shoes then he likely won’t screw up in other areas

Hi, guys. I’m Sarah, a humor and fashion writer who will be burdening you with my thoughts on menswear from time to time. Shall we?

When you’re heading out on a first date (or a second or third – I actually don’t know what those feel like) you want to look as good as you feel because confidence is everything.

Your outfit is indisputably a huge part of that crucial first impression, but clothing can be deceiving. That’s why it’s so much easier to judge by shoes.

I’ve broken down my thoughts on what different styles of shoes say about you because no matter what my ex says, I’m a giver.

What different styles of shoes say about you

1. Boat Shoes

Boat shoes are great because unless you’re physically on a boat when you meet her, you’re pretty open about living a lie. And the foundation of every relationship is brutal, unbridled honesty — so at least you’re truthful about appropriating a lifestyle that isn’t feasible at the moment because reality is a cruel mistress. Plus, they’re effortlessly refined and go with nearly everything.

2. Canvas Shoes

In the warmer months, breathable, streamlined canvas shoes can be great. Unless you’re rocking Chuck Taylor’s and a concert tee because it’s time to give up the dream.

Also, I’m wary of TOMS because you assume the person wearing them is into philanthropy and that all is well and good until you learn that ‘Charity’ is actually his favorite stripper’s name. That was a fun seven months I’ll never get back…

3. Sneakers

Barring Sneakerheads with cool kicks or something akin to retro New Balances, leave sneakers to the Palo Alto tech crowd. It shows how apathetic you truly are when meeting her.

4. Oxfords, Brogues & Saddle Shoes

The official shoe of finance bros who came straight from the office, still in their suit. I commend you for showing up after a long day of making the economy work because someone has to!

They’re respectable but not thrilling, kind of like a boozy brunch without someone leaving the restaurant in tears and your waking up from the post-game nap with someone else’s purse puppy in your tote.

5. Loafers & Driving Moccasins

Loafers and driving mocs aren’t reserved for that study full of leather-bound books you’ve never opened or the Country Club happy hour. They’re comfortable, classic, extremely versatile and make you look like you have your shit together. And the first few dates are all about deception, so why not pretend like you know what you’re doing?

6. Cowboy Boots

Unless you’re auditioning to be part of Magic Mike III: This Isn’t My First Rodeo, leave the Western kicks at home. Aside from all the wonderful ‘riding’ euphemisms you could be making, most of the general population won’t appreciate your blacked-out purchase from SXSW.

7. Dress Boots

In fall or winter dress boots are a great option for making a lasting impression. They’re trendy, always appropriate and speak highly of the individual wearing them. Which means you’re probably already married with a wife and kids in Connecticut and a crash pad in the Village – so I don’t trust you.

8. Sandals

Did you just get back from a Dave Matthews Band or OAR concert? Are you tightening your grip on your fleeting youth, crushing the red solo cup in your hand until the rum and coke spills through your fingers like sand through an hourglass?

Unless you’re taking her to a communal shower (creepy) or your newly renovated yet tastefully decorated beach house (call me!), don’t break out the college-era Rainbows.

Chime in: What shoes do you think make the best impression on a first date?

Follow Sarah on Twitter at her personal handle @sarahsolfails or her parody account, @urbanJAP.

Stylishly Yours,

Sarah Solomon

Photography by Rob McIver Photo

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