You spotted the woman of your dreams, made your way over to her, and garnered enough courage to strike up a conversation. She seemed interested, you made her laugh, sparks flew. You took a deep breath… and asked her out. To your absolute amazement, she responded with an enthusiastic, resounding yes!
Give yourself a mental pat on the back. Well-played, my good man! The hardest part is now over.
Fast-forward to the night of your date with the hottie who fell from heaven. You orchestrated a great plan ahead of time to make sure she will be thoroughly entertained. You're certain she won't be able to resist your undeniable wit and charm. Now, the dreaded part… you gotta figure out what to wear!
Sound like a problem only the ladies have?
Trust me, it's not. She said yes to you, so most likely she's into you, or at least willing to give you a shot. Why not cover all your bases and make sure you look so stunning (within reason) that it makes her disregard any second thoughts she might have had about saying yes in the first place?
Listen up, gents. Women notice things.
They notice insignificant, minuscule things that men don't. They notice the funky way you tie your shoelaces and how you suckle on your teeth to set free that rogue chunk of steak that never found its way down your throat. Women see your fidgeting and your poor posture and they file all these bits of information somewhere in their brains under “Things I Must Learn To Ignore If I Am Going To Be With This Dude,” or if she continues to be smitten with you, under “Things I Will Soon Find Endearing.”
My point is this: The woman you are about to take on a date will notice what you're wearing. Put your best foot forward and make as stellar of an impression as you can if you want a second date.
1. Consider the Logistics
What kind of date is it? Where will you be going and what will you be doing? The park? A picnic? Dinner and a movie? The shooting range? Depending on what you're doing, you're going to need to put on something appropriate to the venue.
Is it possible she might want to continue hanging out after the main part of your date, for example, going for drinks after dinner? Or grabbing a bite after a long afternoon of exploring the city? Is your clothing comfortable and appropriate for the possibilities?
What's the weather going to be like? Unseasonably warm? Chillier than normal? Dress in layers and consider the fact that your date might not be prepared for the colder evening temperatures, which will give you an opportunity to peel off that top-most layer to drape over her shoulders.
An aside: If a woman casually mentions she is cold, immediately take your coat off and wrap her in it. This little action of yours will not go unnoticed (don't forget: women notice everything.) Don't think too long about it, and don't ask if she'd like your coat. She will most likely say no and continue to freeze in silence.
2. My Universal Outfit Suggestion Appropriate for 97.4% of Common Dates
I've alluded to my idea of a perfect outfit for the man going out on a Friday night, and I stand by my suggestion. When you consider the most common date venues and situations, this getup just works: slim, dark, nonembellished denim (leave the True Religions in the hamper), crisp white or light- colored button-down shirt, charcoal gray or navy blazer (you've visited your tailor already, right?), and dark brown leather lace-ups (natural rounded toe, of course.)
3. The Casual Alternative
But you don't always want to wear this ensemble… I hear ya. Here are some other suggestions for a more casual date (i.e. a walk through the park, a picnic, watching a movie, going to a baseball game):
Be comfortable, but not sloppy. No ratty T-shirts from soccer camp your senior year of high school, even under that sweet merino sweater you picked up last week. The collar is all stretched and torn and WOMEN NOTICE THINGS, in case you haven't already caught on.
Instead, throw on a well-fitting Polo or a casual button-down. A broken-in jean may work but don't go too light. The lighter the wash, the less formal it appears, so err on the darker side.
For footwear, you can't go wrong with a pair of driving shoes, Sperry Top-Siders, or even some classic, unadorned low-top sneakers… think Jack Purcell Converse or Superga kicks in white. Wear a light jacket if it makes sense. If you're questioning whether you'll need one, just bring it. The lady may get cold, like I said earlier, and you know what to do if that happens.
Bottom line: You want to layer, so you will be prepared for anything: weather changes, impromptu dinner suggestion from the woman because she enjoys your conversation so much, unexpected bird poop, whatever. Additionally, you want to be one or two levels above the appropriate dress level for the occasion. Trust me, that buffer will work in your favor.
4. The More Formal Alternative
Let's say you'll be taking the lady to dinner, or to a nice bar for drinks. This is when you'll want to pay extra attention to what you put on. For more casual dates, the Polo and crew neck sweater you threw together work just fine, but not for the evening.
You don't need to bust out the tuxedo or the three-piece suit, either. Your goal is to appear classy and put-together, not like you're trying too hard. So, what to wear?
See #2. Seriously. It's an option that will not fail you, assuming you've followed the rules of fit and proportion that have been discussed many times in these style articles.
What other options do you have?
Let's start with pants. Stick with slim cuts, and if you want to deviate from denim, explore dark trousers or slate chinos. The Dockers D1 Slim is a good place to begin.
When it comes to shirts, I highly suggest you stick with a button-down. As far as color goes, white is always safe, but feel free to experiment with what looks good on you. Keep in mind that the color of your shirt should complement your skin tone. If you're still unsure about what looks best, this article by Antonio of A Tailored Suit will steer you in the right direction.
For shoes, a brown lace-up is very versatile and looks great with many color combinations. Stay with brown. I've discussed the different shades of brown dress shoes before, so be sure to take a look at that before heading out the door.
Make sure the sport coat you pick is complementary to everything else. Understanding how color works together is very important, but assuming you have a sport coat in a basic color (navy, charcoal, neutral toned-down pattern), you can't really mess this one up. Go with your gut and pick one that is understated yet fits well with everything else you have on.
A Final Note
Be layered, be deliberate with your selections, and be experimental (again, within reason)… assuming you have the confidence in your choices, and have already defined your own style. If you follow these rough guidelines and put them into practice, you'll appear effortlessly put together in time for your date. Combine that with your stunning good looks and killer smile, and you'll capture her attention the whole night for the right reasons… not because of poor presentation.
What are your ideas of a can't-fail first date getup? Let us know in the comments.