Dress For The Date

So, you’ve scored her number and you’re gearing up for your big date. The tough part is over right? But hang on, let’s not overlook how important it is to look your best. You want to put some thought into your outfit so it’s apparent that you've put together, but not that you’re trying too hard. The key is to be comfortable and confident in what you’re wearing; as they say, if you look good, you’ll feel good. And if you’re feeling good, well, the rest is a piece of cake. We’re confident these four looks will not only get you through your first date but every subsequent one you’re guaranteed to get once she lays eyes on your impeccable style.

The Let’s Grab a Drink Look
So you’re heading to your first date, maybe coffee or a few drinks, and sharp but casual is the key here. Grab a pair of dark indigo denim and a casual button-down shirt like a subtly checked flannel or a gingham. If you’re going untucked, pair it with some desert boots, or, if you’re going tucked, try a classic penny loafer and show her your shoe game is on point.

The Wine and Dine Look
So your first date went well and appropriately-timed gifs and emojis are flying back and forth. Now it’s time to step it up for that all-important dinner date. For this occasion, go with your favorite pair of grey denim or charcoal chinos, and a twill or windowpane shirt. Finish it off with a blazer to pull it all together. Shoe-wise, this look calls for something slightly more dressy like a brown loafer or an oxford. Don’t forget to give your shoes an extra shine before heading out so they’re looking their best. One final tip, if there’s a breeze in the air, offer her your jacket, this chivalrous move will definitely score you a few extra points.

The Weekend Day Date Look
Since things are progressing quite nicely, you’re ready to plan a full day excursion for the two of you. For this date, you’ll need an outfit that’s versatile enough to keep up with any surprises that the day may bring, because, hey, if you’re both having a great time, you never know when the date may end. If the date carries into the evening you’ll be prepared with a few layers. Start with chinos and a casual gingham or striped button down for your daytime activities, you’ll look sharp and be comfortable. Bring along a v-neck or cardigan sweater and layer up as the date progresses; this look can easily transition you into dinner or drinks. You’ll want your shoes to be nice but also comfortable too, so try a boat shoe or casual sneaker.

The Special Occasion Look
Time has progressed and the opportunity to celebrate a special event together has arrived. Maybe you have plans for a nice dinner, a friend’s wedding, or a cultural event. Either way, it’s time to bring out the big guns, and that means a suit. Now you don’t have to get too formal or stuffy, this isn’t the office after all, but you really want to dress to impress. Try your favorite navy or charcoal suit but go with a shirt and tie combo with some color. Alternatively, you can try dressing it down slightly by going tieless. Complete the package and lace-up a pair of oxfords or wingtips and get ready for a classy evening.

Now you can feel confident knowing you’ve got a full repertoire of looks to chose from and you’ll be looking your best on any date that may arise. Speaking of date ideas, if you’re looking for a few tips on how to nail those first few dates, we’ve got you covered right here.

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