Since we were young, society tried to teach us one rule that goes against everything we are. And yet, still today, we choose to do the one thing that rule attempts to end. We judge books by their cover. We know in the first few moments whether we will like someone. Whether we find them attractive. Whether we can respect them. Hell, sometimes we decide then and there if we want to be friends. Ever heard of love at first sight? Completely based on the cover of the book. That is why what we wear on a date night is so important. When we meet our intended, we want to put forth our best selves. That doesn’t mean you have to wear a suit. But it often means you should resort to a T-shirt and jeans.
The process of dressing for a date can get a little overwhelming if you let it. There is a lot to think about. Where are you going? Time of day? Indoor vs. outdoor? First date or anniversary? You want to look like you care. But you don’t want to look desperate. Here is a tip: Stop overthinking it. The trick is effort. If you are going on a date, it shows this person means something to you, and you can show that by dressing appropriately. Now, as far as the first date vs. the anniversary, your dress should be the same. If you’re not showing the same effort deep into the relationship as you were at the beginning (or at least, if you’re showing less), then we have other conversations outside the clothing.
In any case, with that in mind, here are five scenarios and looks that will keep you looking your best so you can give a good impression and hopefully get a second date.
Day date
The day date, whether it is coffee or brunch, is a great first date. There is a lot of pressure when you have a dinner date. Expectations come with the evening. You both know you don’t likely have plans afterward. Dinners are expensive, and you have to invest more when you don’t know the person. Coffee dates are great because it fixes all those issues. It is completely feasible that you have plans afterward, so you have an out. It is low-risk and focuses completely on your interaction. That also means there are fewer distractions. So your look needs to be on point, but you also need to be flexible since coffee dates, if extended, go on walks. Here is the ensemble for you to look amazing.
Shirt – State & Liberty Soho light blue windowpane
Pants – Ministry of Supply Chroma Denim Pant
Shoes – Beckett Simonon Geller Trainers in white
Jacket – Aether M-Phase Full-Zip in Total Eclipse
For this date, it is best to blend fashion with function. Each of these brands and products focuses on making sure you look great while also ensuring maximum comfort and movability. You never know where the date could take you. So, stick to brands like these that put a focus on sharp comfort. These items will look stellar when put together, and you will undoubtedly be the center of their attention.
Dinner date
This date is a little more “serious.” If you aren’t going on a coffee date and removing all the pressures of a first date (or anniversary date), then know that they are there. The pressures are back in full swing. So this is the time when you need to look your best, but not try so hard. Some people will tell you that you need to wear a suit to look your best (and unless you are going to a five-star in New York City, that is probably not true. But if you want to look fabulous and relaxed at the same time, feel free to wear your suit jacket or a sport coat with your dark dress denim. Here is our choice for your important dinner date.
Shirt – Paul Frederick Non-Iron Spread Collar in Black with Orange Dot
Pants – Joseph Abboud Modern Fit Suit Pants in Black
Jacket – Suit Shop Textured Gray Suit Jacket
Shoes – Florsheim Rucci Weave Cap Toe
You look great. Elevated from your other dates (and likely from everyone around you in the rapid casualization of the world), it won’t go unnoticed. You also look laid back, approachable, and someone they can talk to. Now, it is up to you to be charming and make them want a second date.
Drinks
The “let’s grab drinks and see if we vibe” kind of date. Many of us have been on dating apps and gotten that prompt. “I am not here for pen pals and don’t want to waste time. Let’s meet up for drinks.” It may feel cliche to ask if you can buy someone a drink, but the truth is that cliches exist for a reason. They are popular and universally liked. The other thing to keep in mind here is that this is the exact middle ground between the two dates above. It has the casual feel of a day date with the evening heft of a dinner date. So here is how to dress accordingly.
Shirt – Paka The Original Crew Sweater
Pants – The Normal Brand Navy Stretch Chino
Jacket – Bonobos Jetsetter Wool Blazer
Shoes – Bruno Magli Angiolini Dress Boot
Ditching the collared shirt for the sweater is a great way to keep it casual. So is opting for a casual, unstructured jacket (the difference is the lack of canvassing in the jacket lining that keeps the suit silhouette). If you are feeling a little Ron Burgandy, go bold and try a turtleneck under the jacket. It is an underrated look that many don’t feel they can pull off.
Singles mixer
You’re done with the dating apps, and you want something in person. You don’t have a date. You are looking for a date. You are looking to catch attention. Just remember that not all attention is a good thing. The best way to attract the attention you want is the right use of color. Color can be your best friend or your worst enemy. It can make you stand out from a sea of blues and grays or make you feel garish and overdone. Here is a look that will utilize color in the right way and ensure you leave the singles mixer with dates set.
Shirt – DEVIL-DOG Everyday Henley in plum
Pants – Ralph Lauren Stretch Chino in preppy green
Jacket – Y.Chroma Mazarin Cut Shell in olive and plum
Shoes – TAFT Woven Dylan
The subtle use of color is an art form that makes the average man seem larger than life. These pieces go a long way to expressing who you are inside without throwing it in their faces. You can get lost in a sea of the same things around you, refuse to fade away, and stand tall.
Solo mission
You’re done with dating apps. Singles mixers aren’t what you want. You want something like how your grandparents met. You want to see someone across the room and know. You want them to see you and know. So you want to spend your days looking great and putting yourself out there so they can find you. Here is the thing: you never know who you will run into. So here is a great template outfit to model your daily looks on so you can be the person who catches their attention when the time is right.
Shirt – Free Fly Elevate Tee in fig
Pants – Mott & Bow Slim Mosco in dark blue
Jacket – Satchel & Page Montgomery
Shoes – Thursday Boots Captain in Arizona Adobe
Simple and easy. If you want a good rule to follow here, it is quality classics over fast trends. If you look at James Bond’s style, you will realize that he doesn’t wear bright colors or flashy patterns. He is all about quality classics that fit right. That is his trick to always looking good, and it can be yours, too.
Now go out and be charming. Date number two is a lock.
