First Date Style Guide

Have you ever heard the phrase, “It only takes 7 seconds to make a first impression”? In the dating realm, it takes even less.

The truth is, your date is taking a mental note of you and your appearance even before you say hello, shake hands, hug, and settle into your date. So what does this mean for you?

You need to dress to impress.

Your first date outfit is a factor that can make-or-break your date. The outfit you choose for your first date will set the tone for how your date perceives you. You want to start on the right foot and make the best first impression possible.

Creating an outfit takes time, effort, and strategy. We’re here to help.

What Not To Wear

There are a few general rules to first date outfits, but for the most part, it comes down to you and your personal style. You don’t want to be uncomfortable on a first date, as people can sense that. However, there are a few DON’Ts when it comes to what to wear. 

Don’t Wear Baggy Clothes

Baggy clothes are a huge turn-off when it comes to impressing a first date. If your clothes are too big for your body, it’s noticeable. Everyone looks better in clothes that are the right size and a slimmer fit that isn’t too tight and still allows you to be comfortable is the best option for most men.

Don’t Overdo a Fashion Trend

Fashion trends are cool for a moment, but once they’re out of style, they make you look tacky. Even if what you’re wearing is in style, you don’t want to overdo it. Examples of fashion trends are skinny jeans, oversized shirts, large belt buckles, excessive accessories, etc. Keep your outfit simple to make a statement.

Don’t Look Sloppy

This rule is a catch-all for your overall appearance. Your hair, your teeth, your accessories, and most definitely your clothes. If you look in the mirror before you go out and your outfit looks like you threw it on at the last minute, your date will notice.

General Rules

Dial in the Fit

As we alluded to above, the fit of your clothing matters. A lot. For in-depth guidance, check out our clothing fit guides.

Wear Neutral Colors

On a first date, the colors of your clothing should be a mix of whites, greys, blues, blacks, and sometimes dark greens. Once you get more confidence and a better sense of your personal style, you can add in a few pops of color by adding a bright-colored accessory. 

When in Doubt, Dress it up a Notch

While the right formality of dress depends on your date’s setting, as a general rule, you want to take the outfit you’d normally wear and dress it up one notch. For example, if you would normally wear a t-shirt and jeans in the setting you’re in, you can dress it up a bit by switching out the t-shirt with a button-down and the jeans with chinos. 

Outfit Ideas

What would this article be without us giving you a few outfit inspirations to take home!

Here are some of my favorites:

Outfit 1: Keeping it Casual

This outfit would be great for a low-stakes setting like a coffee shop, a walk in the park, etc. With well-fitted jeans and a henley, you’ll look put-together while still keeping the casual vibe you’re going for. 

Featured: Midtown JeansHeather Charcoal Henley

Outfit 2: A Little Dressy

A little more dressy, this is a perfect outfit for an elevated look without being too serious. Wear this at the museum, at a nice dinner, at a show, etc. The grey chinos and button-down pull the outfit together, while the charcoal v-neck sweater is the elevating piece of it all. 

Featured: Grey ChinosHeather Ash Grey Button-downHeather Charcoal V-Neck Sweater

Outfit 3: Formal

This is an outfit you’ll definitely make an impression in. Layers are a great way to let your date know that you take yourself seriously and are thoughtful in what you wear. That said, a formal outfit should be reserved for a setting where it makes sense, like a play or opera, high-class restaurant, or special event with a dress code. 

Featured: Blue Oxford Dress ShirtBlue Ink Quarter-Zip Sweater

Bonus: Having Fun

This outfit is designed to showcase more of your personality. With a dark pair of denim jeans and neutral-colored footwear, you can don a bright-colored button-down to add some flair to your outfit and hopefully your night. 

Featured: Indigo JeansTrailhead Plaid Button-down

Bonus: Shoes and Accessories

When it comes to the shoes you wear on a date, it’s really up to your personal preference. However, we do suggest opting for a nice pair of brown dress shoes or boots. If you’re wearing a more casual outfit, then wearing clean sneakers can work as well. 

The accessories you wear on a date can also add an extra layer of personality, but if you wear too many (or the wrong kind), you may look tacky. We suggest sticking to a nice wrist watch as your sole accessory. 

The sign of a great first date is two people having a great time and enjoying each other’s company. The most important things to wear on your first date are confidence and a smile. If you feel calm and collected, your date will too. 

Style Yourself With These Pieces

Classics You Can’t Go Wrong With

All of our clothes are thoughtfully crafted from scratch to fit men under 5’8″. We focus on creating timeless pieces that you can keep in your wardrobe for a long time.