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What To Wear On A First Date: Outfit Ideas (and More) for Men

Get your first date off on the right foot with our fashion tips. Get your first date off on the right foot with our fashion tips.


There is no doubt that first dates can be nerve-racking. Lucky for you, celebrity stylist Amanda Sanders has got you covered. Literally. She's dressed hundreds of men, including dear friends and long-term clients like Chris Rock. Her expertise is men's style. 

From celebs getting ready for the Academy Awards, MTV Video Music Awards and other notable red carpet events to dressing nervous daters for Bravo's new reality show Love Broker, which helps singles find love, Amanda has seen her share of successes and missteps.

Don't be intimidated, Amanda doesn't use any smoke and mirror tricks; instead, she uses some basic fashion principles and some good old-fashioned dating rules to boost the sex appeal of her clients so they can head on that date with confidence.

Here's Amanda's road map to all around first-date sexiness:


What to do when going on a date right after work? Your work slacks and jacket are OK to wear, but just bring a more interesting shirt, maybe something with stripes or bold colors. This way, you're not looking drab or way too overdressed. Also, don't forget to lose the tie; a stuffy style does not set the right tone for a first date.

So, about that shirt - bright, bold prints or solid? Bold prints are the right choice, especially something graphic but not zany.

“Bright colors can be too much and solids can be too boring,” says Amanda.

A bold print is interesting and makes you stand out without seeming flashy. Bold print shirts are also eye catching, which wins you points in the long run.

Fancy or casual, how do you decide what tone is right? This depends where you are going. If you are unsure what the scene will be like, definitely lean towards the fancier side, just please steer clear of a tuxedo, that's a no brainer. Being too casual and under dressed is worse than being overdressed.

Best fancy outfit? Black slacks, charcoal gray or black sports jacket, bold striped shirt and a pocket square in a contrasting color. As for shoes, leather loafers for the fancier outfits.

Best casual outfit? Dark denim jeans – but please, pick jeans that don't have that cheesy going to a club in the early part of the decade fade and don't pick a fit that's too skinny – button down shirt and drivers. In case you aren't familiar, drivers are like updated loafers. Casual suede loafers are great for the fall and winter.


“How about a little 'manscaping?'" said Amanda.

Get rid of any unwanted hair that your date doesn't want to see, like awkward facial hair and whatever other hair may turn your date off. Nose hair is not sexy.

Date Night

If you asked your date out, you're picking a place. No one likes a wishy-washy date, so think about what your date would like to do and plan around that. Dinner at a nice place is always a safe and enjoyable option. If you want to pick something a little more unconventional, that's great too, just make sure your date is into that.

Make sure your conversation is on point. This means avoiding the past and looking to the present and future. Talk about travel, free time hobbies and passions, work life, but not too much. Ask questions pertinent to the topic at hand.

“Do not interview your date or play 20 questions,” warns Amanda.

Don't worry about it too much, otherwise you'll seem nervous. Good conversation just flows after a little while, and this is indicative of a good first date.

Common Sense

Common sense trumps trends. Don't go with whatever crazy trend you may have seen in a magazine if it’s not your style. In other words, don't try too hard. Keep your personal style in tact; just polish it up.

“I picked out a winter wardrobe for a successful businessman once,” said Amanda. “He was being set up on a date by a friend. The weather was not too cold yet, but it happened to be a rainy day. He bought a pair of navy suede loafers and wore them in the rain on his date. He ended up walking around with soaked feet the whole time and ruined the shoes. This is common sense: you don't wear suede in the rain.”

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A pop-punk classic about first dates.
Last modified on Friday, 23 November 2012 19:55

Laura Vladimirova is a freelance journalist currently based out of New York City. Years of long-term travel abroad have made her a passionate lifestyles writer. Her favorite subjects include art, people, archaeology, travel, cultural events, health, and green living. When she's not typing away at her keyboard or getting her passport stamped, she's probably enjoying the great outdoors.

Website: www.rosebudmag.com/LauraV

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