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What to Wear on a Date: Men's Date Night Shoes Ideas Towards Matching Outfits

What to Wear on a Date: Men's Date Night Shoes Ideas Towards Matching Outfits

Key Takeaways:

  • Choose covered shoes over sandals or flip-flops.
  • Leather shoes exude sophistication.
  • Avoid athletic shoes unless it is snowy.
  • Show effort in your choice of shoes.
  • Comfort is crucial alongside style. 

You both have swiped right and finally a date is happening! And you have cold feet considering how to impress her? Well, be your genuine self; dress up well with nice men's date shoes, wear your confidence and smile- and that's more than enough! But men often get worried about what shoes for a date would look great on them, especially men who aren't much into shoe styling. DO NOT WORRY!

Date Night Men's Shoes Guide

Yes, you heard it right, because our style guide to men's date night shoes and matching outfits will take that pressure off you today itself on what shoes to wear on a first date, what would look best on me and more. It will not only sort your date dilemmas, but also have your feet covered up stylishly and comfortably in the best date shoes for guys, that add charm to your persona.

Shoe Styling and Wearing Tips for Dating

Here are various things to consider before you pick men's date night shoes:

1. Wear Shoes that Cover Your Feet

Though women love to wear sandals and peep-toes, when it comes to men’s date shoes, they don't wish to see their man in sandals, flipflop or for that matter even the Gladiators. Thus, as an aesthetic appeal for your lady, the date shoes for guys should cover their feet properly. Oxford Shoes are to some extent bearable, provided your heel isn't peeping out from men’s date shoes!

2. Leather Shoes Exude Style

Premium leather dress shoes are any day better than any other date night shoes men should wear, because leather dress shoes have that sophisticated aura around them. Plus, if you have to spend longer hours with your lady, these leather shoes to wear on a date will keep your feet very comfortable and active. Also, if your woman is vegan, ensure man made leather.

3. Avoid Wear Athletic Shoes or Boots

Men with a great body build up tend to make the mistake of wearing athletic shoes or boots as shoes for a date. Avoid the mistake, because women are least interested in such a look, unless it's a winter, snowy date night.

4. Wear Shoes that Showcase Your Efforts

When a woman sees that a man has taken interest in his own aesthetics, she knows that he is mature and considerate enough to do the same for her. Plus, very well presentable in her circle. Thus, your shoes to wear on a date must be based on attire ideas also that are stylish, casual yet a very smart choice.

5. Wear Comfortable and Smart Shoes

What shoes to wear on a first date should not be just answered by the word 'SMART'. You need to feel your feet well and cozy in the same. Men's date night shoes might demand longer hours or a cozy dance, so dress up appropriately.

Men's Dating Shoes & Outfit Recommendation

Stylish Footwear and Outfit Ideas for Men on Dates
Shoe Type Recommended Outfit Occasion/Setting
Tassel Loafers Jeans and T-shirt, or Blazer Sudden dates, Casual outings, Movie date
Monk Straps Jeans and Blazer Dinner date night
Oxford & Derby Shoes Suit Formal dates with business partner
Sneakers T-shirts and Chinos/Pants Classic and evergreen; avoid multi-colored or flashy sneakers
Cap-toe Shoes Versatile for both casual and formal settings Versatile settings
Casual Shoes (Slip-ons) T-shirts and Shorts Beach or resort dates, Picnic dates, 


Now let's come across which shoes will compliment what attire as that perfect pair of date night shoes men would love to wear. Because not just the attire but also the kind of shoes plays a major role in impressing your lady.

Because don't forget, ladies always have some kind of shoe fetish by default in them! So their chip must register a good date memory with you! So let's head off to our style guide of men’s date night shoes and matching outfits.

1. Tassel Loafers Look Great with Every Casual Outfit

If the date is planned on a sudden note, then Tassel Loafers are the safest bet as stylish, smart footwear and perfect men's date night shoes. Because these adorn any kind of casual outfit very well, be it jeans and T-shirt or a Blazer with Jeans.

Also Read: Best Shoes to Wear with Jeans

2. Monk Straps with Jeans and Blazer

One of the most enduring shoes to wear on a date are the Monk Strap Shoes, which are sophisticated, stylish, smart yet casual footwear and quite trendy. Keep the color in tandem with that of the blazer and you will never go out of fashion ideas for the date nights.

3. Oxford & Derby Shoes with Suit

Oxford style dress Shoes for men

When the date is not a blind date and your woman is highly sophisticated, then the best is to keep the attire formal. Pick a suit color (avoid black, brown) that matches your persona. And pair these up with tan/brown or navy Oxfords or Derby shoes as per the colors of the overall attire.

Also Read: Oxford vs Derby Shoes Comparison: What's the Major Differences

4. Sneakers with T-shirts and Chinos or Pants

This combination and textile footwear are an evergreen men’s date shoes style. But what you must take care of is that your shoes to wear on a date should never be multi-colored or flashy. See the whole idea is that 'her attention should be on you' and not fully on your shoes!

Also Read: What Shoes to Wear with Chinos and Khaki

5. Cap Toe Shoes with Casual As Well as Formal Attire

See there are some basic things to consider, when you wish to look smart, stylish via your footwear and attire on a date night. Cap toe shoes are one kind of shoes which can pass off as a great accessory with casual as well as a formal setting. Like tow tone cap toe or monk-strap cap toes look great on jeans, chinos and capri-pants, while cap toe oxfords or cap toe oxford Style lace up are fit to compliment the suits and formal pants. So as per your own style and comfort, or the restaurant setting, pick up your shoes for date.

6. Casual Shoes with Ultra-Casual Attires

Casual Shoes with Casual Attires for Men

Here we can talk about casual shoes to slip-ons, which go with T-shirts and Shorts. Suppose your date is happening at a beach, or a resort with a pool, or such a similar setting. Then keep the shoes and the attire befitting the setting. Slip-ons are the best idea, so that you can slip in and out of the shoes and perform various fun activities with your lady, like a beach walk...like a sit down talk with feet dipped into the pool and more. The ideas to dress up for date night are as many as your imagination!

Also Read: Best Men's Shoes to Wear with Shorts for Dapper Look 


Whatever men’s date shoes or overall attire you may finally wear, don't forget to feel confident about. And how will you do that? Well, a mirror will always be your perfect guide to showcase how you look and what will make you look better and confident. No harm in taking extra tips from friends. But the final call should be as per your own persona and looks.


1. What to wear on a dinner date for men?

Opt for a smart-casual outfit, like a crisp shirt with chinos or dark jeans, paired with dress shoes.

2. What not to wear on a casual date?

Avoid overly casual items like gym clothes, flip-flops, and anything too sloppy or wrinkled.

3. How can I look attractive on the first date?

Dress well, maintain good posture, smile, and show genuine interest in your date.

4. Can I wear formal on my first date?

Yes, if the venue is upscale. Otherwise, smart-casual is usually more appropriate.

5. What grooming tips should I follow before a date?

Ensure you're well-groomed: trim facial hair, style your hair, and maintain good hygiene.

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