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What to Wear on a First Date: A Casual Dinner
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April 24, 2018

When going on a first date, you want make the ultimate first impression with your words and your style. A less formal setting like a laid back, casual dinner can take some pressure off, but this doesn’t mean you have an excuse to wear a t-shirt and sneakers. You should always look good from head-to-toe no matter the setting, especially if you want to land a second date. Check out our top picks for a casual dinner date outfit for men:

The Shirt

Kenners Button Down Collar Non-Iron Casual Shirt

A t-shirt can look sloppy on a first date, so reach for a casual button up shirt instead. These shirts are always a great choice and pair well with almost anything, from jeans, chinos, and anything else you can think of. Except sweatpants. Never those.

The subtle patterns and pops of color in the Kenners Button Down Collar Non-Iron Casual Shirt and the Poplar Button Down Collar Non-Iron Casual Shirt are just what you need to make a good first impression and not scare them off with an old t-shirt.

The Pants

[Flat Front Non-Iron Cotton Khaki Pant In Navy

Pleated dress pants can make you feel like you’re still at the office, but a nice pair of flat front khakis can be dressed down enough for a casual night out. Jeans are always an option, too, just make sure they’re a solid, dark wash. We love our Flat Front Non-Iron Cotton Khaki Pants in Tan and Navy.

The Shoes

[Steve Madden Highlyte Boot in Tan Suede

While sneakers are an acceptable choice of footwear in most settings, your date will definitely notice your ensemble from head-to-toe. Opt for your nicest pair of boots instead. You should also make sure they’re in good condition and buff out any scuffs beforehand. We like these options from [Steve Madden. The’re perfect for when you don’t want to wear sneakers but also want to avoid stiff dress shoes.

Posted In: Blog Posts

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