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Hypothetical situation: You’re out on the town one night, and you manage to connect with someone despite both of your inebriated states. They’re interested in following up with a date next week, just you two. The day comes and you’re ready to go. You stop by your barber for a trim, hit the gym for that post-workout pump, and now its time to get dressed. Shit. Now what?

Showing up to a date dressed poorly can be an instant deal breaker for many people, or at the very least it could leave a bad first impression. Don’t do that — be better. Being well dressed doesn’t mean getting suited up at any opportunity, it means dressing appropriately for the occasion, wearing clothes that fit, and understanding what colors work together. Simple in theory, yet it can be complicated in practice. We’ve had our fair share of missed opportunities and fashion faux-pas, enough for us to learn from our mistakes. We want to pass down that knowledge in hopes of helping you impress your date with your style choices. In order to do so, we present part one of the three part series.

Dressing for the occasion is arguably the most important factor in dressing well. It’s so easy to spot the guy who doesn’t have a clue about how to dress appropriately, yet it’s so easy to avoid. We’ve all seen the guy who shows up to a graduation ceremony wearing beat up sneakers and ripped jeans, or proudly wears a dress shirt and tie to a casual meal at Chipotle. Don’t be that guy. When you’re getting dressed, consider the setting of the place you’re going to. These suggestions are by no means set in stone, but you can use these categories as a general guideline to help figure out what to wear.

Casual

Casual refers to occasions such as a coffee date, casual dinner, walk in the park, etc. You want to be comfortable and laid back so you can focus on enjoying the date and making a good impression. Think sneakers, jeans or chinos, tee shirts, henleys or casual button downs, and maybe a light jacket if the weather calls for it. If you need a hand picking out a jacket, check out the style guide from earlier this month. You could consider leather derbies or oxfords if your wardrobe permits, but just keep the environment of the date in mind so that you’re not uncomfortable or uptight.

 

Upscale Casual

You’re going to want to step it up a little if you’re going to a fancier bar or upscale restaurant, which is where upscale casual comes into play. Oxfords or slim boots paired with chinos or even dress pants can be a great choice here, meaning it’s usually a good call to leave the t-shirt at home. Instead, opt for a casual button down or dress shirt, along with a round neck sweater on top if it’s going to be chilly. A really nice pair of jeans can work too, as they’re not ripped or dirty. Dressing for an upscale casual date can be tough since it sits in a weird grey area casual and formal. However, if you are able to do some research to scope out the venue, you may be able to get a better understanding of what to expect.

 

 

Semi Formal/Formal

 

If you manage to land a date at a formal event or really high-end restaurant, you’re probably far past the first date. If not, give yourself a round of applause and . In terms of footwear, you’re definitely going to want a pair of oxfords or brogues, so if you don’t have a pair you better leave time to stop by Nordstrom on the way. If for some reason you’re still considering wearing jeans, you might as well go ahead and cancel. At the very least, you’re going to want a pair of dress pants and a dress shirt, along with a tie. Suits look great here, but try to save your black suit for weddings or funerals, and opt for a lighter option like navy.

 

 

While there are certainly a ton of other factors that influence the outcome of an outfit, it’s important to assess the environment first so that you can dress accordingly. Feeling out of place on a date sucks, and preparing or at least thinking about what to wear in advance can do wonders for your confidence and first impression. Next week, we dive into the fit and styling of common garments to take you a little deeper into developing your own sense of style.

About the Author

I am a writer with a love for food, travel, and menswear. My free time is filled with clothing or furniture design, while working on new recipes to add to my repertoire. I am passionate about learning and strive for personal and professional growth through my work and hobbies. My weekends are spent travelling, creating tasting menus with friends or visiting local bars and restaurants.

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