The Perfect Shoe for the Perfect Date

No matter how far along you are in a relationship, there are some dates that just deserve the right outfit – and the right shoes. The question is, how do you know you’ve chosen the perfect shoes? This doesn’t just go for women, by the way, even though they’re more likely to have a closet full of stylish footwear. Men pay attention to these things too, and they deserve advice on their date-night footwear just as much as anyone else.

There are several considerations to take into account when selecting your shoes. For example, someone with bunions wouldn’t want to wear overly restrictive shoes. In that case, they might want to look specifically for bunion shoes for women or men. These types of shoes aren’t just orthopaedic tennis shoes, by the way; they can also be stylish and fun, just the ticket for date night.

Best Date-Night Shoes for Women

How can we blame the women who are obsessed with shoes, when there are so many gorgeous options to choose from? Without getting too specific in our recommendations, these are some of the top picks for various types of dates.

Ballerina flats or stylish sandals for lunch at the best sandwich shop in town

Every town has that one place that’s cute, affordable, and somehow unbelievably delicious. Taking your date to lunch at this type of place says that you want to share a great meal together, but still keep things on the informal side. Ballerina flats or sandals are in keeping with this approach; they aren’t too formal, but they can still look great.

Boots for the movie theater

Movie theaters tend to be on the colder side, so it makes sense to wear shoes that will keep your feet and ankles warm. Plus, some well-fitted boots won’t get in the way as you walk to the nearest street-food stand after watching the film.

Heels or wedges for a romantic evening

There’s just something sexy about heeled shoes that can’t be replicated by other styles. However, this doesn’t mean you’ll have to sacrifice your comfort to look your best; there are certain styles of heels and wedges that are almost as comfortable as flats.

The Perfect Shoe for the Perfect Date

Best Date-Night Shoes For Men

When it comes to men’s shoes, there’s one surefire way to elevate the look: wear something made from leather. Even the best-quality tennis shoes are still just tennis shoes, but a leather loafer is a different story.

Loafers for coffee, lunch, or hanging out

Loafers bridge the gap between formal and casual, but they’re definitely more suited for casual settings. If you want to make an effort without looking like a try-hard, leather loafers are a great choice.

Brogues for romantic dinners or other special occasions

When you want to step it up a notch, slip on a pair of well-fitted brogues. They’re sleeker than loafers, and definitely more elevated than tennis shoes. Whether you’re sitting down at a fine dining experience, or taking in some iconic local views, brogues will get the job done.

Dos and Don’ts When Selecting Your Date-Night Shoes

Looks aren’t everything, whether you’re talking about your date or your shoes. These are some tips to follow if you want to choose the perfect shoes for your date.


  • Wear shoes that are clean and in good condition. This may seem like obvious advice, but you’d be surprised at how many people are oblivious to the state of their shoes. Being clean from head to toe shows the other person that you’re making an effort, and the reverse is true as well. If you show up in grimy shoes, you’ll give the impression that you don’t really care.
  • Consider your entire outfit. You can match colors, use your shoes to provide a contrast, or just go for a shoe + clothes pairing that’s reliable and obvious. Extra points if you can put together something that’s unexpected, but still looks great! An example of this would be an outfit that’s all dark or light colors, with shoes that follow a contrasting color scheme. White clothes with red shoes, navy clothes with camel-brown shoes, and so on.
  • Keep it simple. A really special occasion would justify you pulling out all the stops, but nine times out of 10 you’d be better off going with your old standbys. As in, thigh-high boots would be overkill, but your personal favorite pair of pumps or loafers would probably do the trick.
  • Wear something comfortable. This will be an easier task for men than for women, but everyone should follow this rule. You shouldn’t have to be in pain to look fashionable – plus, you’d just be detracting from your enjoyment of the experience if your feet are killing you the whole time.


  • Overthink it. It’s always best to be your authentic self on a date, so you might as well reflect that with your shoes. You may be tempted to wear your flashiest, coolest pair of shoes, but that could be setting a standard that’ll be hard to top when the occasion calls for it.
  • Wear shoes that don’t fit your personality. It’s understandable if a guy wants to impress his date with his most important-looking brogues, or a girl wants to show off her new heels. The problem comes when neither of them are accustomed to these styles – and it really shows. You’ll be at your best when you’re comfortable in your surroundings, and that includes your shoes.
  • Wear shoes that are painful or difficult to walk in. This is more applicable to women than to men, thanks to the existence of sky-high heels and other extremely impractical shoes. If you’re focusing all your energy on ignoring pain or staying upright, you’re focusing on the wrong thing.

The Takeaway

Some people overthink it, others don’t think about it enough, but one thing is for sure – picking the perfect shoes for your date is important. Whether it’s the first date or the 100th, your shoes will always help you make the right impression.

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