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

Chime In

  • MNuta

    It may be just me imagining things but this article makes all these shoes sound bad: boat shoes= living a lie, chucks are the sign of a failed rockstar, sneaks show you don’t care, dress shoes are corporate and boring, western boots make you a cowboy and dress boots make you untrustworthy while sandals show you’re a hippie or surfer (no surprise here). The conclusion I can draw here is that loafers and drivers are the sh*t.
    All jokes out the way, IMO, good shoes to wear on a date are more casual dress shoes like brogues or derbies,( dress or work) boots, and maybe more grown up, minimalist sneakers.

    • Brian Sacawa

      Aren’t they, (loafers and mocs) though?!

      All kidding aside, I think one of the most important things abot choosing footwear for a first date is to make sure your shoes look well cared for and in good shape.

      It also depends on the venue. Dinner at a nice restaurant and/or cocktails calls for one kind of shoe, while going to a fair or rock concert would call for another. Has to be appropriate for the occasion.

      Thanks for the comment!

      • Jim Voll

        You took the words right out of my mouth. They all have their place depending where you are going. I may want to wear one thing on a night out but I never want overshadow what my wife is wearing. so the same would go for the first date I would think. I always get complements from woman when I wear my tan cap toe derbys or my blue suede shoes

  • d_g

    welcome, Sarah!

    i’m…… i’m just as new as you, here, but it still seemed like a nice thing to do to welcome you. good luck!

    • Brian Sacawa

      Thanks for the feedback, d_g! Good to have you and hope to see you around more often!

  • Paul Brosnan

    Welcome! I found this article very humorous (therefore you did your job quite well) I can’t wait to read more from you. Welcome to the team!

    • Brian Sacawa

      Glad to hear it, Paul! Stay tuned!

  • Frank Wilder

    Don’t fight the old — create the new – Frank Wilder

  • BigMike

    Sarah, I truly believe your way off on your “Cowboy Boots”. With 501’s, a bespoke sport coat or suite jacket, a tailored shirt and of course a pocket square. Even a big city girl like you would swoon!

    Excellent article all in all though! This site could use a stylish women”s perspective!