First Date Wear: Simple Fashion Hacks To Stay Stylish

It might just be the most challenging sartorial puzzle a man can encounter: the first date. Do you dress up and make sure that you show the occasion its appropriate respect, or do you dress down and keep it casual? Pants or shorts? Collar or no collar? Which colors fit the occasion?

Fortunately, a first date doesn’t have to be as complicated as all that. Especially if you follow a few of our favorite style hacks:

Style Hack #1: Use Clear Packing Tape to Clean Up

So you don’t want to wear something too over-the-top…but you still want to look nice. A good compromise is to wear a casual button-down shirt. But you’ll have to make sure that it’s also well-groomed. recommends turning some clear packing tape inside out to form something of a half-glove—you can then use this “glove” to roll off the lint and debris that’s plagued your shirt. Once you’re finished? Simply toss it away.

This is especially effective if you’re wearing a dark pair of pants like these Super 100’s Gabardine Pleated in Navy.

Style Hack #2: Turn Up the Color With Stylish Laces

So you’re tired of the same old khaki-button down-boot combo. Is there any way you can spice it up with something a little outside the box that won’t make you look like you’re completely clashing? After all, on a first date, you have to wear something versatile enough to look good just about anywhere, whether that’s a restaurant or out to a show.

The trick: wear brightly-colored boot laces. It doesn’t take very long to change up your usual boot style with a pair of laces that draws the eye without drawing unwanted attention. Sites like are full of thousands of laces that fit just about any possible permutation you can think of.

Style Hack #3: Do “In Between” Haircuts for Inexpensive Grooming

Some barbers will offer you a discounted “clean up” haircut between your usual haircuts. It’s nothing major, just a way to stay neat and trimmed—and to catch any unwanted hairs that they might have missed the first time. If your favorite barber offers a discounted “clean up” within three weeks of your  previous hair cut, get it done up before the big date—it will add to your confidence without subtracting too much from your wallet.

Style Hack #4: Ditch the Work Pleats

Not sure which pants to wear on the big date? Go with a quality pair of pants without pleats in order to add plenty of casual versatility: not too formal, but still sharp. Here are some of our favorite “first date” pairs:

Fashion designer Tom Ford once said that dressing well is a form of good manners. We couldn’t agree more—especially when it comes to a first date. A few little touches like the hacks listed above will show your date that you’re interested, well put-together, and ready for anything.