First Date Fashion: A Complete Guide to Styling Your First Date

Whether it’s your first time meeting someone in person after matching on a dating site, or you’re meeting a total stranger through a matchmaking friend, first dates can be nerve-racking. Will things feel awkward?

First Date Fashion styling

Will you have anything in common? Knowing how to approach the date is vital if you want to build a long-term, positive connection, and one of the biggest elements to get right is your outfit. Studies have shown that people make their first impressions of you within 27 seconds of meeting, so your fashion sense plays a huge role in the way you’ll be perceived on your date.

In this guide, we’ll be breaking down first-date fashion for both men and women, to make sure that you’re setting yourself up for success from the very beginning.

First Things First: Where Are You Going?

The location of your first date is one of the most important elements when it comes to deciding what to wear. If you’re going for a classic mid-afternoon coffee date, then you should keep things casual, and opt for an outfit that is put-together but cozy. Alternatively, if you’re going to an upscale restaurant, then your style will need to reflect the classy environment.

Fortunately, deciphering restaurant dress codes doesn’t need to be difficult. Once you’ve booked a table, call the venue ahead of time to confirm what their dress code is (accounting for the day of the week that you’ll be there) and then take some inspiration from an online guide to dress codes. This way, you’ll be able to find the perfect pieces that work with the environment and make a great impression on your date!

Styling Ideas for Women

Wherever you’re going, you can usually find a midi dress that will suit the occasion or dress up a quality pair of jeans with a nice top, but when you’re planning your outfit there are still a number of tweaks or additions that you can make to elevate your look and wow your date. For example:

Hair and makeup

Your hair and makeup can either make or break an outfit, so it’s vital that you get it right when you’re heading out for a date. If your date is activity-based, then wearing your hair up in a sleek ponytail will keep you looking put-together throughout. At a coffee or dinner date, however, you can afford to be more adventurous with your hairstyle, so curling or straightening your locks and wearing them down will make a big impact.

Consideration should also be paid to your makeup. A natural, neutral look is usually a safe choice for a first date, and you can always add a pop of color to your lips if you want to pull your outfit together in a bolder way.


Accessories are a wonderful way to effortlessly polish and finalize your look. From timeless jewelry pieces to a classy designer bag, the right accessories tell your date that you’ve taken time to put your outfit together, showing them that you’re serious about finding a true connection.

First Date Outfit Tips for Men

Traditionally, men have had a harder time dressing for a first date, but that shouldn’t stop you boosting your style with these easy tips!

Invest in quality

When you’re dressing for a first date, your outfit should show that you’ve invested in quality pieces. A jacket or shade from a global lifestyle brand like Moncler can make a big statement, which is great for perfecting your first impression.

Avoid oversized pieces

Although oversized clothing is trendy right now, try to avoid these pieces on your first date. When your clothing is baggy or too big, it can be hard to style your outfit to look smart and put-together, which can damage the impression you make on your date. Stick to tailored or slim-fit pieces for the wow-factor!

Choose your accessories wisely

While men don’t have as much choice when it comes to accessories, you can still make a big impact if you select the right accompaniments to your outfit. If you’re meeting outdoors, then you can’t go wrong with a classic scarf and gloves combination. Drinks after work? A leather laptop bag combines professionalism with style – and what you do for work is a great conversation starter! 

By following these three top tips, you can elevate your style and make a brilliant first impression, so it’s worth investing the time into making some simple changes.

Dating is hard, especially if you’ve only spoken to somebody online before deciding to meet in person. Take some of the stress out of your first date by being prepared, and you’ll be far more confident to get the conversation going. By using this guide when you’re putting your outfit together, you can make sure that your sense of style isn’t holding you back from finding the person of your dreams!

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