Now Reading
First Date Outfits Guaranteed To Get Men A Second Date

First Date Outfits Guaranteed To Get Men A Second Date

first-date-outfits-men-style-rave

First dates can be both exciting and nerve-wracking. You’ve finally secured that date, and now it’s time to make a memorable impression. While personality and conversation play a significant role in securing a second date, your outfit can also speak volumes and play a role in how things turn out.  First Date Outfits Men

The key to a successful first date outfit is to be yourself and feel comfortable in what you wear. Confidence is attractive; so choose an outfit that makes you feel your best. In addition, pay attention to grooming and hygiene, and endeavor to be punctual. With the right outfit and a great attitude, you’ll increase your chances of not only having a successful first date but also securing that coveted second date. To help you put your best foot forward, we’ve compiled a guide of first-date outfits for men that will leave a lasting impression.

Here are first date outfits guaranteed to get men a second date…

#1. The Low-Stakes Coffee Link-Up

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by ProTrending (@protrending)

The most casual first date is a coffee date, but it’s still not casual enough to wear the sweats you’ve been wearing while binge-watching Suits on Netflix. Start with a weekend-appropriate outfit that includes a crewneck sweater in a solid color without any graphics paired with clean-cut, untoasted sneakers. Inject character into the combo with a discrete dress watch or a pair of pants that appear to be fitted but actually feature a hidden elastic waist. Every first date requires you to keep a few things secret.

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Slimster |📍NYC | Style (@stylesbyslimster)

Shop editor’s choice

 

#2. The Leisurely Weekend Hang

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by UpscaleHype (@upscalehype)

The best first date outfit feels comfortable but can handle the possibility of mutual enthusiasm over time, whether ducking into a pasta restaurant or an impromptu afternoon cocktail. This is true when an activity is scheduled, such as a museum visit, a concert in the park, or a leaf-peeping stroll. While you’re out and about, a blouson is a stylish and practical choice that can withstand an unexpected downpour. The fit wouldn’t be affected by a pair of clean sneakers, but gum-soled Wallabees look smoother and will still stop your dogs from barking.

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Najm Loyd (@steelojeem)

Shop editor’s choice

 

#3. The Post-Work Drinks

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Jean-Claude (@newkissontheblog)

This is where the spotlight hack truly, um, shines. Going from work to a meet-up can be a problem if your company’s dress code is aggressively severe. While you ditch your “office-y” blazer after work, slide in a Western belt that can make you stand out in both the cubicles and the bar, while possibly giving you something to speak about. Top-notch leather goods are a simple spot to flex some personal style. In addition, derby shoes seem posh enough to escape any CEO side-eye.

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Slimster |📍NYC | Style (@stylesbyslimster)

Shop editor’s choice

 

#4. The Dinner-to-Dancing Night Out

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by UpscaleHype (@upscalehype)

Make a first date outfit that exudes the same excitement since you have a difficult-to-get dinner reservation and the possibility of a big night out afterwards. That leather jacket you’ve been saving for the ideal scenario? The time has come. Put on your chunky shoes for stomping. The move with a vest and necklace, which elevates a fresh white tee, maybe the actual improvement in this outfit.

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Damson Idris (@damsonidris)

Shop editor’s choice

 

Check out more first date outfit inspiration…

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Bouba Chouchane (@chouchane.b)

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by UpscaleHype (@upscalehype)

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Najm Loyd (@steelojeem)

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Jean-Claude (@newkissontheblog)

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Rag (@fits_by_rag)

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by MUBI IDRIESS 🌪️🥷🏾 (@mubiix)

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Bouba Chouchane (@chouchane.b)


For the latest in fashion, lifestyle, and culture, follow us on Instagram @StyleRave_


This is a Style Rave original content exclusively created for our readers. If reproduced, distributed, transmitted, cached, or otherwise used by any other publishing house or blogs, such use should provide a direct link to this source article. Use of and/or registration on any portion of this site constitutes acceptance of our Terms & Conditions and Privacy Policy.  

—Read Also

Subscribe

Never miss the latest. Subscribe Now

    Style Rave participates in various affiliate marketing programs, which means we may get paid commissions on editorially chosen products purchased through our links to retailer sites.

    All rights reserved. No digital content on this website may not be reproduced, published, broadcasted, cached, rewritten, or redistributed in whole or in part without prior
    express written permission from STYLE RAVE. Use of and/or registration on any portion of this site constitutes acceptance of our Terms & Conditions and Privacy Policy.

    Copyright © 2025 Style Rave NG LLC, dba STYLE RAVE

    Scroll To Top