The Playbook For The Modern Man

Women Describe The Most Appealing Clothes A Man Can Wear On A First Date

“Hot but chill.”

You rock up to the cafe five minutes early. The sun is shining. The coffee smells ~amaze~. The waiter stops to chat. Your date arrives in a light summer dress. You hug awkwardly, but not too awkwardly. She shimmies into her seat. For a moment, you think all is well. Then you realise: aside from a pair of purple Crocs, you’re naked.

While the above situation is a ‘night before’ nightmare for the overthinkers of the world, the fact remains: choosing what to wear on a date is nerve-wracking, and can either make you more attractive to your date or immediately put them off.

So: get it right.

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While a pair of black skinnies and white tee is a timeless choice, it’s kind of boring (especially considering the hectic outfits kicking around at the moment). However, you also have to consider what you’re used to: if a jeans and tee are what you’re most comfortable in, it’ll show when you rock up in pink chinos and a baby blue polo.

To navigate this minefield judgemental coffee shop, we scoured the internet for advice. Much of it was, to put it frankly, bullshit. But we panned for gold, and believe we’ve found some gems that will help you look, “chill but hot.”

Here are the three most important things you need to do.

Make an effort

Perhaps the smartest advice we saw comes from Mensxp, who asked seven women “whether they liked men who are fashionable or chill.” The conclusion? Let’s just say, as they put it, “you should upgrade your closet.”

In other words: have a style, whether or not that style is deliberately unkempt or Leonardo DiCaprio in The Great Gatsby.

This is backed up by a study conducted by The Essential Man, who asked 101 women of all backgrounds, jobs, ages and locations what a man should wear on a first date.

Unsurprisingly, effort, and the respect it signifies came up numero uno: “As a woman, I will make an effort to look nice and pretty for my date because I want to respect his company and effort for asking me out — and I would like the person to feel proud to be with me.”

“When a guy dresses like a teenage boy and it looks like he didn’t care at all, it is distracting and really kills the first impression.”

Examples of clothes or accessories that show you’ve made an effort include: a nice timepiece, a well-maintained pair of Chelsea boots, or a box fresh pair of sneakers.

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Be well-groomed (& well fitted)

Your Viking beard is more than welcome. But the stench of BO, whale blood and seven-day old ale? Not so much. As one woman told Mensxp, “I have never found a man hot in an ill-fitting sweatshirt. I like men who take care of their looks.

“Wearing clothes that suit you and keeping yourself groomed is extremely sexy.”

This was reiterated by The Essential Man, who writes: “Ill-fitting clothes wrecks havoc on your attractiveness. It makes you look fatter, shorter, and sloppy. Wearing clothes that fit properly not only makes you look better, it allows you to look good even when you’re dressed in something as simple as a t-shirt and jeans.”

Especially important clothes to wear fitted include: jeans, collared shirts, tees (if you can’t get one that fits right off the rack), leather jackets and denim jackets.

Dress to match your personality

“I find men who are smart really sexy. Being able to have long conversations with them about things is a big turn on. And if they dress the way they think, now that’s a deadly combo,” another woman told Mensxp.

Examples include: glasses, baseball caps, bling (or lack thereof) and colours (or again, the lack thereof).

Your next date awaits.

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