very guy’s been there -- you’ve gotten her number, she seems cute and likes the same kind of music you like, and you even picked a restaurant that your friend recommended. It has food you don’t have to eat with your hands! The peak of class, and the beer is still reasonably priced. The second date is in the bag and the first hasn’t even happened yet. 

But then, it hits you. You have no idea what to wear. Fine dining is out of your budget, so your Windsor Knot skills (you do know how to tie a tie, right?) are going to waste. What exactly is “casual” and how are you supposed to pull it off? What’s too fancy, but not stylish enough? If these are questions you’ve asked yourself in the pursuit of a casual date outfit, you’ve come to the right place. 

First Steps: What to Look For in an Outfit

Don’t Panic, You’ve Got This

The most important questions for ANY outfit you’re looking at are the five below -- almost everything else is secondary. Pick up the piece of clothing you’re thinking about, and ask yourself the following: 

  • Is this clean? 
  • Is this stained?
  • Is this wrinkled?
  • Does this actually fit me? 
  • Is this appropriate for the weather/season?

These are ESSENTIAL. They are some of the first things that are obvious to anyone looking at your clothes. The thought that most commonly occurs with several of these are “Eh, but who’s going to notice?” The guy or girl sitting across from you will, guaranteed. They won’t tell you, and you’ll think you have gotten away with it, but it is all but assured any group chat they’re in or close friends they have know all about how weirdly stained your sleeves were.

A good guide on how to get out various types of stains (Courtesy of Reader's Digest)

Wash, remove any stains, and iron anything you’re considering to wear. The stain removal infographic above should be more than adequate to take care of anything with enough time and attention, but a stain stick is a good thing to carry in the car or in a pocket. You shouldn’t need it, of course, but there’s no reason to stay nervous about the state of your clothes when you can pick up some “insurance” for cheap at a gas station. 

The amount of people that do not know how to iron or consider it unnecessary is astounding considering the difference it makes. Not only does it look better, it feels better to wear, and there is nothing better to soothe pre date jitters than smoothing out some wrinkles. Make sure to pay attention to how the clothing you have needs to be ironed

The fourth question of the above is not thought about as often as it needs to be. The question of “fit” seems to elude many guys, so let us be excruciatingly clear.

  • Just because it does not fall off of your body, does not mean it fits.
  • Just because your Mom bought it for you, does not mean it fits.
  • Just because it fit a couple years ago and you haven’t changed THAT much, does not mean it fits. 
  • Just because it fits your buddy and he’s roughly the same body type as you, does not mean it fits.

When we say something “fits,” we mean not only that it is physically possible for you to put it on, but also that it is flattering to your body size and type. A piece of clothing does not have to be of any particular kind of “cut” to be flattering, but it does have to be of dimensions appropriate for you. Cut is more a matter of comfort than anything else, at least in terms of the basic considerations of this guide.

This is incredibly easy for men’s clothing, especially pants. If you are in doubt, get a tailor’s tape and measure. There is little to no excuse for wearing a pair of pants that expose your ankles unintentionally, or that require a belt to keep up. Get your measurements in inches, and check them against your clothes. If they are all too small or too big, it may be time to purchase some new outfits

We will not be discussing at great length the suitability of your outfit to the weather and season. If you insist on wearing boat shoes and shorts in the winter, there is nothing a style guide can do for you. An umbrella as an accessory is the only additional note here. A good quality umbrella is quite practical and offers plenty of opportunities to keep close to a date while keeping them dry. 

Second Steps, Quite Literally: Shoes and Accessories

On The Road to Style

A nice selection of solid and well kept footwear. 

First and foremost -- closed toe shoes. No man’s feet are that pretty, it’s not up for debate. Open toed shoes are for wading up creeks, manning boats, and fighting to the death in the Colosseum, all of which are terrible first dates and thus doomed no matter what your choice in footwear. 

From there, once again, it mostly comes down to cleanliness. Almost any type of boot or shoe can be made to work if they are shined, freshened, and match the colors of the outfit. It is best if they are neither overly ostentatious or understated (sneakers are not exactly a strong choice here for both of those reasons).

If you can shine your shoes, do. This is not difficult to do and makes all the difference, especially with older and well worn shoes. Pick up a kit from a corner store with a color close to the pair of shoes you have and set to it. It takes maybe twenty minutes and will make you feel like a new man. As a bonus it might make your dad proud, but that is a pleasant side effect and not the main goal at the moment. 

In terms of accessories -- you can never go wrong with a good belt, matching your shoes if you can manage it. Suspenders are out, as they are almost exclusively meant to be worn underneath a jacket or blazer of some sort in more formal situations. Jewelry is also perfectly acceptable, though once again, preferably understated. A small necklace, bracelet, or earring/stud (if you are pierced) can accent a casual outfit well and show some personality. 

A note on watches. Many articles will extol the virtues of watches in signaling all sorts of things to potential dates, and offer a wide selection of different styles. This is mostly in vain. It is a piece of jewelry the same as any other, and if it matches the outfit or has some personal meaning, then by all means wear it. 

Everyone knows you actually look at the time on your phone, anyhow. If you were hoping to use it as a means of showing wealth, this is much better communicated through the ordering of an appetizer or two, and drinks. 

Third Steps: A Word on Color

It’s Not As Hard As You Think

A commercial selection of shirts. You’d hardly imagine there are this many colors from the way most guys dress. 

The concept of “matching” and other color considerations are sometimes nebulous to guys, but it can be quite easy. These simple guidelines will see you through most potential issues: 

  • Navy Blue and Black do not go together. Full stop.
  • Wearing White is usually not a great idea because of how easily it stains.
  • Stick to one pattern per outfit.
  • “Light” or “Dark” shades of the same color (usually brown or black) are best for shoes and belts, even if they aren’t identical.

That should see you through the most common faux pas. If you care to be a bit more daring than that, there is never anything wrong with throwing a bit of color into an outfit, bright or dark. A little goes a long way; a burgundy pair of pants with a gray sweater or a salmon shirt over khakis can show an amount of effort most guys will never bother with. 

Graphic tees and shirts are not to be considered. If you’d care to be seen as an adult, there is plenty you can do to still be fun and interesting without being childish. Hobbies and media properties are ample fodder for conversation, but have little place on your body no matter how casual the date. If you care at all how you are dressing for an occasion, leave your band shirts at home. 

All in all, a first date is nothing to panic over. With a little attention paid to cleanliness, good fit, and careful accessorizing, there’s no need to worry about first impressions. Following this guide, you should be more than able to focus on the food, the conversation, and, most importantly, your date! 

Apr 28, 2022