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First Date Outfit Ideas (for the Guys)

Posted by TheLittleLink Cufflinks on

There are definitely some classic ways to make a good first impression on a first date. From bouquets of flowers, walks on the beach, a flashy car, or expensive bottle of wine, there are endless strategies to woo someone. With all the complex and potentially expensive ways to start off on the right foot, it can be easy to let some aspects slip to the wayside.

There’s also no doubt that you’re trying to dress to impress on a first date. The stress of choosing an appropriate outfit on top of planning a fun date can be especially overwhelming. Don’t stress though! Follow these simple first date outfit ideas perfect for an outdoor adventure or a formal night out.

Outfits for first dates for guys

Casual Date

There’s absolutely nothing wrong with keeping things casual, especially on the first date. While you might be out to impress someone, there’s no need to overdo it with a flashy date when you ultimately just want to get to know each other a little better. Keep things casual and call your first date a “meet and greet,” that way expectations don’t soar too high, too fast.

That said, there’s no reason you can’t dress to impress even while keeping it casual. In fact, a low-key date is a perfect way to express your personal style. Whether it’s a casual coffee date or lunch, a patterned or colorful button-up or polo shirt is a great way to express yourself.

To finish off your casual look, throw on a nice pair of dark denim pants and some comfortable loafers. Being well-dressed says a lot about someone versus just throwing on a t-shirt and shorts. While comfort is key when keeping things casual, it’s probably best that you save the tennis shoes for the gym.

Tshirts for casual dates

Formal Dinner

A formal night out could be a great way to impress someone for a first date. If you know how to dress, dine, and drive in class, there’s no better way to take someone out. The key to a successful formal dinner date is preparation. Schedule a ride in a nice car, make a reservation at a five-star restaurant, and of course, plan your outfit so you don’t look thrown together.

dressing formally for dates

A formal dinner is the perfect opportunity to bring out a nice suit. It’s important though, to also consider the atmosphere before choosing your outfit. If you’ll be outside, wear a light-weight button up with a colorful necktie to show off your fun side.

Blake Puppy Blue Tie


If you’re inside and the season is cold, stick to the classic white and black or navy. This white necktie with feather accents shows that you’re clean and classy.

Atlas White Necktie with Feather Accents

Night Out on the Town

If you’re idea of a perfect date night includes a night out on the town hopping from one bar to the next, we have the perfect first date outfit ideas for you! Many nightclubs or bars enforce strict dress codes which often ban jeans, t-shirts, tennis shoes, shorts and hats. While this might seem limiting, this dress code essentially sets you up for success.

Wearing a leather jacket on dates

In fact, it’s pretty hard to be over dressed unless you’re donning a full suit. The best way to impress on a night out is by showing class while still appearing that you’re ready for a good time. Now is a great time to pull out that sports coat or blazer, but rather than pairing with a necktie or a button-up, grab a clean white shirt. It’s no secret that it gets hot inside of bars, so this look allows you to easily cool off by just taking off the coat and heading to the dance floor.

basketball cufflinksBiker Cyclist Cufflinks

If you might catch a game at the bars you’re heading to, compliment your attire with some unique cufflinks! You don’t have to wear a tux to don the perfect cufflinks. In fact, team or sport-specific cufflinks might act as a great conversation starter.

Outdoors Adventure

outdoor datesThere’s nothing better than an outdoor adventure. What could be more exciting than taking your date on an exploration of nature? If your normal day-to-day involves exercise outdoors, this is a great place to plan a date. This way, you’re in your element and comfortable with your surroundings.

While being outdoors requires a more flexible, casual wardrobe, it’s still important to be fashionable and look your best. It’s definitely not necessary to wear a collared shirt, but you should still probably steer clear of athletic shorts.  For this outdoorsy date, choose a comfortable t-shirt or hoodie (depending on the season) and top it with a stylish jean jacket. Stick with nice shorts and clean, comfortable tennis shoes.

Flatbill cap To top it off (literally) add a hat to your style! Flat-billed hats are trending right now and they’re a perfect way to show off your unique fashion sense.

No matter what your ideal date is, with these first date outfit ideas, you’ll be dressed to impress. The Little Link has everything you need to accent your perfect look. Check out our latest styles today and good luck on your first date!

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