First Date Or Weekly Ritual, Here Are Some Of Our Favorite Date Night Ideas And Shoes To Match | Style Guide Skip to main content

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First Date or Weekly Ritual, here are some of our Favorite Date Night Ideas and Shoes to Match

Whether it’s your first date or a special night out with your partner, deciding where to go and what to wear is an important step. To help out, we’ve created a list of some of the most popular date night ideas along with our recommendations for shoe styles. But remember, no one knows you better than you, make sure you’re comfortable in your choice of place and your outfit.

The featured image is the Talladega Moe Toe Venetian Driver in Cognac.

Dinner & Movie

As date night ideas go, dinner and a movie might be great if you’ve been together for a while, but neither idea makes for a good first date. Movies don’t let you talk – a first date is meant as a time to get to know one another, and dinners can really be a drag especially if you find out right away that it’s not meant to be. They aren’t great as first date ideas but it’s hard to beat that line up for an established couple’s date night. Generally, a dinner date is a more formal affair and calls for, at the very least, a button-down shirt and dark wash jeans with dressier shoes, all the way up to a sport coat and dress pants. Check out some of our favorite styles below.


One of the stronger first date ideas, getting coffee allows you to relax and get to know one another. A coffee date means daytime and casual, but don’t go overboard on the casual. It’s always important to look like you put some thought and effort into your attire. It shows respect for yourself and for your date. You’ll never go wrong with a collared shirt, fitted jeans, a sweater, and a nice pair of casual shoes. These are some of our top styles for a coffee date.


The lunch date works for both a first date idea and a daytime version of the couple’s date night idea. Find a place that is trendy but not so popular you can’t get a table or too loud to hear each other talk. And by all means, avoid fast food chains and the $9 all-you-can-eat buffet. The question remains: What to wear for a first date lunch? Keep it simple with a pair of jeans with an untucked dark wash chambray shirt, add in a boot, and you have a great look to accompany your burger and fries.


As date night ideas go, this is a good one. If it is a weekday evening your attire will likely be dictated by what you wore to work. If so, push the boundaries a little and add a little interest like some fun socks or shirt. If you do have time to make it home to change or it is a weekend evening, then you can get as creative or as simple as you want. It is evening so no matter what you wear keep it to a darker color palette. The drink date requires an urban vibe and nothing has more of that than a sleek boot or stylish slip on.


Meeting outdoors, maybe for a walk in the park, picnic, or a trip to the zoo or the beach all work for first dates and couples date. If you’ve chosen one of these, we will assume this is a warm weather date. Linen pants and an untucked linen shirt or well-fitting shorts and a polo shirt are good options. Even though the date is outdoors and casual, unless there is surfing involved, do not wear flip flops. No one wants to see your toes. A stylish yet casual shoe with a modern profile is the perfect choice.

Sporting/Music Event

Sporting events and concerts can be an excellent first date or date night idea. Both call for casual attire. It’s a good time to break out your favorite team t-shirt or sweatshirt with a pair of jeans. Make yourself comfortable but keep your style sophisticated. No matter what the sport or what band is playing, a sneaker always fits the bill.

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