Free Worldwide DHL & FEDEX Express Shipping

Free Exchange and Return

5 Men’s Date Night Outfit Ideas with Shoes to Match

  • July 25, 2023
  • Shoe Guide

When planning a first date, your outfit speaks volumes about your style and personality before you’ve even uttered a word. One key element often overlooked is the choice of shoes, which can make or break your overall appearance.

In this article, we’re exploring men’s date night outfit ideas. Whether it’s a romantic dinner date at a fancy restaurant or a casual first date at a local cafe, your shoes can set the tone for the night. Let’s dive in!

Men's Date Night Outfit Ideas with Shoes, men at date with his girl

Classic and Elegant: The Suit and Dress Shoe Combination

The first outfit in our array of date night outfits is the timeless classic – a well-tailored suit paired with the right dress shoes. This is the perfect first date outfit for formal outings and places with a dress code.

Choosing the Suit

Choosing a suit is more than just a matter of fit and fabric. The cut of your suit should flatter your body shape. For instance, a slim fit suit may be ideal for lean figures while a classic fit can work well for most body types.

Choosing a Dress Shoe

The best materials for shoes in this context are high-quality leather or suede. These materials not only lend an upscale vibe to your outfit but also ensure durability and comfort, making them an excellent investment.

When considering the color of your shoes, aim for a pair that is either the same color as your suit jacket or a shade darker. Black or brown leather shoes work well with most suit colors. If you’re wearing a navy or grey suit, burgundy or oxblood shoes can add a stylish twist.

men shoes for date night

Casual Cool: Pairing Jeans with Stylish Sneakers

Nothing beats the effortlessly cool combination of t shirt, jeans and stylish sneakers. Ideal for a more relaxed date setting, such as a movie night, casual dinner date or coffee date, this casual outfit speaks volumes about your laid-back yet trendy style.

Choosing the Jeans

Choosing the right pair of jeans is paramount. Depending on your body type and personal preference, you could opt for slim fit, straight-leg, or even a relaxed fit. The trick is to go for a pair that flatters your physique while ensuring comfort. Avoid wearing light wash jeans. A darker wash looks sleeker, making it an excellent choice for a great date outfit.

Choosing the Sneakers

Sneakers are not just about comfort; they’re a statement of your style and personality. Opt for minimalist, low-profile sneakers for a more refined look. White sneakers, black, or navy are versatile and can complement most outfits.

In the context of date night shoes, sneakers are an excellent choice. They exude an air of youthful energy and casual ease, all while keeping your comfort at the forefront. Remember, the key to nailing this look is to ensure your sneakers are in good condition and they are a clear pair.

Smart-Casual Charm: Chinos and Loafers for a Polished Look

This versatile look straddles the line between formal and casual – chinos with loafers. This combination is perfect for a variety of date settings, from grabbing coffee to an art gallery visit, presenting an air of polished charm without appearing too formal.

Choosing the Chinos

Choosing chinos is all about finding the right fit and color. Opt for a slim or straight fit, ensuring they are comfortable yet flattering. As for colors, stick to neutrals like beige, navy, or olive for an easily adaptable look.

Choosing the Loafers

These slip-on shoes are the epitome of smart-casual footwear, offering a blend of comfort and style. When considering loafers, it’s essential to look at different shoe materials. Classic leather loafers project an image of sophistication and are perfect for a refined look. Alternatively, suede loafers provide a softer aesthetic, ideal for a more relaxed yet stylish vibe.

loafers for date night

The material you choose for your loafers significantly influences the overall outfit. Leather loafers pair well with a crisp button-down shirt and a blazer, while suede loafers complement a simple polo shirt or a casual plaid shirt.

Relaxed and Trendy: Incorporating Denim with Boots or Chelsea Boots

Our fourth men’s date night outfit idea takes a turn toward modern trends while retaining a laid-back vibe. We’re talking about the stylish blend of denim with boots or Chelsea boots. Perfect for an outdoor concert, a craft beer tasting, or even casual daytime dates, this combination seamlessly fuses comfort and trendiness.

Choosing the Denim

Denim is the quintessential casual wardrobe staple. Opt for slim-fit or straight-leg dark wash jeans for a sleeker appearance. Avoid overly distressed or ripped jeans to maintain a certain level of sophistication in your mens date night outfit.

Choosing the Boots

The right pair of boots can elevate your look from ordinary to memorable. To help you choose, we’ve provided a short men’s boots guide.

Men’s Boots Guide:

  • Lace-Up Boots: These traditional boots offer a rugged, outdoorsy vibe. Opt for a pair made of sturdy leather for durability and style.

  • Chelsea Boots: Offering a sleek, refined aesthetic, Chelsea boots are a go-to for many men. These slip-on boots, often made of leather or suede, boast a streamlined silhouette that pairs impeccably with denim.

chelsea boots for date night

  • Chukka Boots: Chukka boots, also known as desert boots, are characterized by their unlined leather or suede design and two or three pairs of eyelets. They’re versatile and can be dressed up or down.

  • Brogue Boots: Brogue boots are high-ankle boots that have decorative perforations (broguing) and serration along the pieces’ visible edges. They’re suitable for semi-formal or smart-casual occasions.

  • Hiking Boots: For more casual or outdoor dates, sturdy hiking boots can convey an adventurous spirit while ensuring optimal comfort and protection.

Personalizing Your Style: Adding Unique Touches to Stand Out

True style goes beyond adhering to trends; it’s about creating a unique identity that reflects your personality. When it comes to a great date night outfit, personalizing your style plays a significant role in making a lasting impression. Perhaps it’s a unique accessory, like a vintage wristwatch or a bold pocket square. Or maybe it’s a distinctive shoe style that deviates from the conventional.

One word of advice though; avoid wearing flip flops on a first date. You want to be the best version of you, and that does not mean showing your toes!

Making the Right Impression

At Pierzel we pride ourselves on our handmade, bespoke quality footwear, and made-to-order shoes that blend luxury and style. Crafted by master cobblers in Spain, each pair reflects a timeless design and attention to detail.

Our aim is you to look good and feel comfortable. After all, true style is a blend of personal taste and comfort. So, we encourage you to experiment with these mens fashion date night looks. Use them as a guideline, but always feel free to add your own little detail like pocket square or nice watch.

  • Share this to: