Table for two

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Worried about what to wear on a date? You should be. Dates can be harrowing experiences that can fill one with self-esteem issues and performance anxiety. But with the right outfit, these problems can be overcome, allowing your true personality to shine through and win the affections of whoever is on the other side of that table. Or end up in a flaming wreck.

Here’s how to look great doing it.

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In a situation like this where you are looking to dress to impress, it is best to stick to tried and tested classics. Leave that Game of Thrones t-shirt at home. But don’t wear a suit, this is not a job interview (those are easier). But that doesn’t mean that you show up in sweatpants. Be sure to wear a jacket, they make you look taller and wider. And you never know, she might get cold.

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Here’s a closer look at this lovely windowpane check jacket from Suit Select, one of my favorite Japanese labels. It is an ideal half lined summer jacket, cut close to the body, with one central vent at the rear. Wear something that fits well, something comfortable. This outfit would be ideal for dinner at a classy restaurant, or an evening at the theater, the kind where you go to watch plays that is.

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Bring flowers. Flowers work. If you can’t, wear one of these. Often overlooked, jacket lapels are meant to be accessorized. You could actually pop a real flower in there, but that runs the risk of wilting. And since real flowers don’t come with polka dots, these are the next best option. I’ve tonally matched mine to my shirt and pattern matched the tie. If you are on your way to the movies, lose the tie. A patterned button down shirt like this can make the transition from smart to casual real easy, and that makes it a fundamental shirt in any mans wardrobe. Look at that magnificent collar roll.

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Take a shower. Be ready 30 minutes before you need to get there. Get there on time. Punctuality, which is something lost on many today, is extremely attractive.

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How to be punctual? Wear a watch. It saves you that one second it takes you to reach into your pocket to pull out your phone. Strap on some bracelets too. ‘Mewellery’ is in, fam. It is understandable if that term made you cringe. Bracelets are a very simple, yet stylish addition to your outfit that can really make a difference. Layer woven bracelets with leather ones, throw in some beads, go crazy and embellish that wrist.

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Don’t match your trousers to your jacket. No suits, remember. Well fitting indigo denim works for all occasions. Don’t leave all the dressing up to the ladies. Dressing sharp for someone shows respect, and shows that they deserve your best. And check that fly.

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I cannot stress this enough. Wear good shoes. Women love shoes, theirs, other women’s, and yours. Don’t be afraid to throw on some colorful socks. Be confident, look like you mean business, and have all the fun.

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That’s about all you need to get that first impression down. Then it’s just a matter of relying on your personality to get you through. Yeah. Being interesting and interested and stuff. What a drag. If you get stood up or things don’t go right, big deal. When your’e dressed like this, nobody will suspect a thing.

Go home and watch Die Hard (or 500 Days of Summer if you really feel bad) and drown your sorrows in yogurt. Best night ever.

Jacket from Suit Select

Tie from Van Heusen

Shirt from Code

Jeans from American Bull

Socks from Allen Solly

Shoes from Clarks

Photos by Roshan Chikodi

Location Courtesy: Walkin Studios

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