What To Wear On A First Date - First Date Outfit Ideas

They say you never get a second chance at a first impression, but when it comes to dating, you kind of do. Your first date outfit will make a lasting impression. And if the outfit you were in for the first impression was not your best look, this is your chance to make up for it. When it comes to what to wear on a first date, men have a lot to think about from big questions like What is appropriately casual, but still presents me in the best light? to more mundane questions like Does this shirt match these pants?Who needs the aggravation of stressing over a first date outfit? As it is, 40% of men say that they are “scared” when first interacting with a potential mate. Don’t let fretting over what to wear on a first date turn you into another statistic. Take a page out of the Black Lapel book and bring your A-game with these great first date outfits for men. And to all you guys out there who are already seeing someone, or married, these outfits are just as good for a 10th date or date night with your spouse.

First Date Outfit #1: The Gallery Show

When the date is upscale, like going to see some world-class art, a world-class look is in order. Step up to slacks and a blazer. The well-put together look seen here is just the kind of look you what you want her seeing when you pick her up.

First Date Outfit #1 - Flatiron Fine Check Blazer, Charcoal Gray Pants, White Dress Shirt

Here Orfeus (Yeah, this dude’s name is Orfeus! How cool is that?) combines a traditional blue and gray color combination with modern slim cut tailoring for an updated take on a classic.Orfeus wears a Flatiron Blue Fine Check Custom Blazer and Charcoal Gray Custom Pants with a White Solid Broadcloth Custom Dress Shirt. Throw on a pair of black lace-ups and accessorize with shades and a vintage car (optional) to create a first date outfit that’ll really get her motor running.

First Date Outfit #2: The After-Work Drinks

Meeting for a drink sounds casual, but any after work date means you’ve got to balance your nine-to-five look with your first date outfit. But don’t sweat this fact. A great fitting suit is a turn on for a lot of women.

First Date Outfit #2 - Warm Gray Sharkskin Suit, Light Blue and Blue Striped Dress Shirt

Women aren’t the only ones who feel good about a suit, wearing a suit will make you feel as confident as a two-time Olympian (like Tobias here, who actually competed in the Beijing and London Olympics as a swimmer).Tobias moves from business to pleasure with ease in this Warm Gray Sharkskin Custom Suit with a Light Blue and Blue Striped Broadcloth Custom Dress Shirt. Add a blue/gray tie and sharp pair of wholecut shoes and there’s no telling where the night will lead.

First Date Outfit #3: The Dinner & A Movie

Suits are great, but they’re not ALWAYS appropriate. Casual dining and movie theaters are the kinds of places jeans and sneakers do the trick. But it doesn’t mean you have to be completely dressed down. Exhibit A:

First Date Outfit #3 - Royal Blue Blazer, White Dress Shirt

Darren, the model for these photos, couldn’t help but attract attention. In fact, we had to stop this photo shoot for a moment so he could kick some game at an adoring fan who happened to walk by.

Darren dresses up some casual kicks with a great fitting pair of jeans. He also follows rule number one for dressing up denim: stay dark. He brightens up the look at the waist with a Royal Blue Custom Blazer, White Solid Broadcloth Custom Dress Shirt and a pink accent in the pocket square. Top it all off with a set of bracelets and a pair of signature glasses, and that seat on the bench won’t be empty for long.

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What to Wear on a First Date?

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