2 Different Outfit Approaches to a First Date: Breaking Down How to Think About Building a Getup

2 Different Outfit Approaches to a First Date: Breaking Down How to Think About Building a Getup
Ask these two questions to immediately improve and simplify your style process.

Special thanks to Nothing New sneakers and Thursday Boots for partnering with us on this feature, two brands making sharp footwear that will have you looking great long after the first date.

What’s the biggest thing on your mind before a date? What you’ll say? How early (or late) to arrive?

How about what you’re going to wear?

If you’re like me, it’s easy to obsess over picking just the right outfit. But you should ask yourself: is all that deliberation getting you anywhere? Are you actually asking the questions you should be asking when you assemble an outfit? 

The 2 Questions You MUST Ask Before Creating A Look

The “first date outfit” is a tired old dog in the men’s style world, so why are we talking about it on Primer – again? 


The first date outfit is so universal – and the stakes for getting it wrong feel so high – that it’s the perfect laboratory for gaming out exactly what you want to accomplish with your style. You want to say everything you possibly can about yourself in a few pieces of clothing.

Big, existential ideas come into play with a first date outfit: class, tribe, status, ego, personality  … but don’t be overwhelmed by all that. Essentially, there are two questions that you can ask yourself in order to pin down what you need your clothes to do for you:

What do I want my outfit to say about me?

Yes, this is a very personal question. Generally what most guys want to convey on a first date is something on the spectrum of “I’m a sane, interesting, and confident person that participates in society.” That’s a good place to start, but your first-date style is an opportunity to say so much more – and it’s an opportunity you must seize.

What do I need it to look like based on where I’m going?

This can be tricky because you don’t always know what you’re in for on a first date. In fact, that’s kind of the point. You need to be ready for a range of situations, from hanging out in a coffee shop for hours, or walking into a stylish cocktail bar on a “whim.”

If this is all a little too theoretical for you, don’t worry. Let’s look at some examples.

Example 1: Dressing up your sneakers

men fashion date outfit short sleeve blue henley gray dress pants gray sneakers

Sneakers: Nothing New, $110 // Knit Henley: Find., $30 // Dress Pants: Goodthreads, $40

What does this outfit say? Our first outfit has an urban feel with its monochrome-y look and laid back sophistication. On first glance, it seems quite casual.

But there’s still something polished about the look. So what is it?

The sneakers from Nothing New may be made from plastic bottles and old netting but they’re well-built and stylish. They’re monochrome and lower profile than a regular old Chuck Taylor, which makes them more boot-like than the average sneaker.

The pants, technically chinos, have a subtle pattern and are essentially a cotton dress pant. The polo is actually not a polo, but rather a knit henley from Find. that lends polish as well. (For more info on how to dress up a henley, check out our awesome guide).

Layer this affordable bomber jacket over top and you've got a modern outfit that expertly mixes the dressier elements (the material and fit of the henley, patterned dress pants) with the more casual ones (nylon bomber jacket, canvas sneakers).

men date outfit idea bomber jacket henley dress pants sneakers

Sneakers: Nothing New, $110 // Knit Henley: Find., $30 // Dress Pants: Goodthreads, $40 // Bomber jacket: Amazon Essentials, $40

What does this outfit say to you? Style is highly individual, and one person’s takeaway might be very different from another’s. To us, this outfit says “I pay attention to my presentation and modern style without chasing trends. I’m intentional about my life without being rigid. I read, watch, and consume culture but I want to hear what you think. I’m friendly – you won't be embarrassed introducing me to your friends.”

Making something polished out of casual elements – it says a lot, doesn’t it?

Where can this outfit go? All together, this checks all the boxes of a perfect, thoughtfully smart casual outfit that can go anywhere and do virtually anything you’ll find on a first date.

This one might appeal to the guy whose instincts tell him to dress up, but who worries about being overdressed. I personally tend to err on the side of too dressy rather than risk looking like a schlub, but a date can sour quickly if you make them feel under-dressed. Or worse, being overdressed can communicate you don’t quite belong to the tribe well enough to understand what’s expected.

What makes the sneakers unique is what makes them interesting: eco-friendly and thoughtfully handmade with a sleek silhouette and True Stitch construction. In other words, these are smart casual sneakers that can swing more formal or more chill as needed, just like you. See other ways we wear them here.

Now let’s look at something a little different.

Example 2: Dressing down your boots

A person standing posing for the camera wearing a denim jacket and striped sweater

Wingtip boots: Thursday Boots, $220 // Denim jacket: Levi's, $69 // Striped sweater: Goodthreads, $30 // Tapered stretch chinos: Dockers, $30

What does this outfit say? This one starts with Thursday Boot Company’s wingtips, which are definitely a more dressy choice than sneakers. These are less chunky than a typical Red Wing work boot but more rugged than a Chelsea boot – classically stylish and functional as well.

The wingtips are paired with more casual chinos than in #1, but with a striped knit sweater and medium-wash denim jacket. The colors are a little more broken up here, which clearly gives a more informal or preppy vibe than the first outfit.

Quick tip: if your jacket looks like something someone would ask if you want to hang up, you’re wearing outerwear. In this case, the jacket is a layering piece that blends into the outfit as a whole.

To us, this outfit says: “I respect tradition but I'm not outdated. I’m comfortable in t-shirts or suits (and I own both). I dress well but with a preference towards styles and brands that last. I’m thoughtful – and also a man of action.”

Where can this outfit go? This outfit also goes just about anywhere, thanks to the juxtaposition of dressy with casual. So what distinguishes it from outfit #1?

Think of it this way: this outfit buys your date a coffee with an impromptu walk around the park and ends with a dessert from “that new place you've both heard so much about.” It’s got a dash of the practical and the classic. It’s more Paul Newman than James Dean.

That’s the beauty of a nuanced ensemble: it’s a little tough to say where you could be headed.

date night casual outfit idea men

Wingtip boots: Thursday Boots, $220 // Denim jacket: Levi's, $69 // Striped sweater: Goodthreads, $30 // Tapered stretch chinos: Dockers, $30

While many modern eyes look at brogueing (the decorative pattern of little holes) on boots like this and think dressy, historically, brogues have been a sign of informality. These are waterproof, full grain leather boots with reinforced eyelets and Goodyear welt construction. They’re here to party.

Struggling with a date outfit? Start with shoes

If you're 20 minutes out from leaving for a date, staring into the abyss of your closet and really at a loss for where to start, start with your shoes. People tend to check out a guy’s shoes for clues about how he thinks of himself. As you can see with these two outfits, the footwear direction has an incredible influence on not only the style but perceived formality of the end look. Using your shoes as a starting point will guide you with how dressy or casual the other elements need to be.

Your turn: Look at the outfit you were about to wear

So now that you know how to answer our two questions, what about the outfit you were going to wear on your next first date? How does it answer these questions? What does it say? Is it who you want to be? Could it be better? Consider these tips:

  • Pick a style piece you feel good about and go from there
  • Dress up something that is clearly casual, or
  • Dress down something that is decidedly formal
  • Add details that will signal that thought went into your getup

This approach to a first date outfit–or any aspect of style that requires intention–can revolutionize your look. Starting with these two guiding questions, rather than just winging it, can go a long way toward making the perennial first (or fiftieth) date outfit less of a question … and more of a statement.

What’s your go-to outfit for a first date? Tell us in the comments!

Stillman Brown

Stillman Brown is a writer and TV producer who has created prime time content for National Geographic, Discovery, Travel Channel and many others. His interests span science & the natural world, personal growth, and food. He lives in Tulsa, Oklahoma.