A Stately Date Night

The saying “dress to impress” has never rang more true than when referring to a date night. First impressions are not only important, but pairing it with confidence will not only make you look good, but feel good, too. Who wouldn’t want to project that type of positive attitude on a date with that special someone? So let’s delve into what to wear on date night.

First tip is to dress appropriately for where you are going. A day date tends to be more on the casual side, while a dinner and a movie can be a bit more sophisticated. Comfort is always key when picking clothes for a date night, and if you are not comfortable in your clothes it can leave you feeling fidgety and distracted. And we all know that the only thing you should be focusing on is having a great time on your date!

Second, let your true colors shine through your clothes for a date night. Even though you want to show off your personality and express yourself, try to avoid anything too bright or patterned as you don’t want to come off as flashy. By keeping things simple with your date night outfit, you can still be stylish and fashionable without appearing to be boring. Instead, lean towards colors that match well with basics. Navy, charcoal, dark green, maroon or beige are great examples of colors that can be mixed and matched with almost any look. 

Lastly, like with any smart outfit, make sure you are well groomed and that your date night clothing is clean, wrinkle free, and well-fitted! You can wear the world’s trendiest items but if the items don’t fit, you can come off looking careless or outdated. To pull it all together, add an accessory to top off your date night outfit. A classic watch, belt or even a color coordinated sock can be a great topic of conversation to break the ice on your date. 

To help you come up with different outfit options for what to wear on a date night, we chose 3 different date scenarios and how to dress for each of them. Whether it’s a casual coffee date, a day outing, or a fancy dinner, putting effort into your look shows that you not only care, but that the date actually means something to you, too.  

Coffee Date

Greet the day with a pair of colored chinos and a classic henley, layered with a flannel and/or a bomber jacket. Clean sneakers are always great date outfit ideas for guys, but you can take it a step further by adding a classy boot to tie together a chic look. This men’s outfit can easily take you onto the next activity of the day, whether it be a park stroll or to the nearest museum.

Alt text: Collage of men wearing plaid jackets, henleys, slacks and boots.


 Collage of Stately items


Happy Hour

Meeting straight after work or wanting to get your date night started as soon as possible? Need to be stylish at the office but still remain trendy with your men’s nightlife fashion? The trick to a day to night transitional outfit is all about layering! Pairing a dark jean with a long sleeve polo and sweater for a more casual vibe or a basic button down under a trendy jacket will help your pieces look cohesive and polished. Curious about how to nail that day to night outfit for men? You can read all about it in our previous post here

Collage of men wearing slacks, sneakers, boots and sweaters with jackets and sunglasses.

Collage of Stately items.


Dinner and a show

Now this is the time to step up your game. Although no one is asking you to put on a full piece suit when dressing for a nice dinner date, a nice crisp shirt layered under a blazer with a pair of chinos and oxfords would be the icing on the cake. Your date will appreciate the extra effort and you will look like the sharpest man in the room!

Collage of men wearing blazers, dress shirts, slacks and dress shoes.

Collage of Stately items.


Like what you see? Our stylists are happy to help you with all of your date night looks. Request these pieces in your next box today. Happy Styling!




Dottie Day
Stately stylist, writer, and designer based in Los Angeles, CA