The fancy restaurant date
Let's be clear, no girlfriend or wife is going to fault you for putting in too much effort. Showing that you care is most important on a date (and in a relationship) and paying attention to what you are wearing is great a way to show you care. Getting dressed up shifts your mindset and sets the tone for the night ahead.
If you are headed to a nice dinner start with a well-cut blazer (and know your way around a wine list). With a dark sport coat as your foundation you can take it up or down a notch based on what you pair with it.
Juxtaposition to a tailored piece
As always, be mindful of the fit. Notice how the sleeves hit just right at the wrist, with the cuff of the shirt peeking out slightly, touching the base of the thumb. Pay attention to these small details. They make a difference. We have received so many emails from the wives and girlfriends of our customers thanking us for helping their men wear better fitting clothes. It matters!
Don't be afraid to add a subtle detail like a pocket square or scarf. These small additions might feel a bit forced at first, but once you are used to them (and the compliments!) you won't forget to add them.
Adding a bit of color with a sweater underneath your jacket is a nice way to soften your appearance, especially if you are coming straight from the office. Our Madison Quarter Zip sweaters in lightweight Italian Merino Wool are excellent pieces to add to your date night look. They are rugged enough to throw into your duffel bag, yet they work well with your blazer and our Dress Pants (as seen below). The addition of the sweater is an easy add-on with major impact. It helps put your date at ease and makes you look less business-like.
The local pub dinner date
If your dinner date calls for a casual look, our Weekend Shirt works well as an anchor for the rest of your outfit. It's a collared shirt so it still keeps you looking proper, but the untucked tail and comfortable fabric makes it suitable for any date.
A denim or chambray shirt always looks great, and opting for Chinos (as seen below) or Cords will make your date take notice. If you are a die-hard denim guy, wear your darkest rinse jean, but not with chambray. Try an oxford shirt instead.
A great-fitting Leather Jacket (like ours) adds a boost of sex appeal. The classic styling and high quality leather will have you looking sharp, and her wanting to be close.
The adventurous dinner date
The best kind of date includes some spontaneity. So if you don't know where the night will take you, dress for anything. That's why our tried-and-true combo of blazer with jeans works in this situation. The jacket will get you into most venues, and the denim won't leave you overdressed in case you hit up an indie rock show.
A lighter wash jean contrasts with the tidiness of the blazer and gives you room to add other casual elements. Of course, above all, pay attention to fit.
A solid shirt and classic sneakers will tie it together nicely. Don´t forget to offer her your jacket if the evening gets chilly.
The last word on first impressions
In the age of dating apps, the first in-person meeting holds even more weight. The key is to impress your date, but not appear as if you are forcing a look. That's why we recommend the "dressed-up casual" spectrum for most any night out. You want to look approachable yet put together, thus our emphasis on fit above all else. You speak volumes with proper fit even if people who are looking at you can't necessarily pinpoint why you look so good.
We'll impart you with one last bit of wisdom: Women will notice your shoes (and socks) and your watch. So stick with classics like desert boots, brogues, penny loafers or understated sneakers. Choose a watch that revels in minimalism and is based on the looks of a classic timepiece such as a Rolex Datejust or Omega Speedmaster. And don´t forget to have fun!