A Men's Guide to Dressing for Date Night

A Men's Guide to Dressing for Date Night

Whether you have an upcoming date with someone new or you and your significant other have a weekly date night on the calendar, you always want to look your best when heading out with that special someone.

From having dinner at that new spot that you finally got a reservation for or grabbing a cocktail before a show, it's key to put in some extra effort when getting ready for date night. This is a great way to show your date that you care (which is just as important for a first date as it is for a 100th date!), to ensure you look as good as you feel, and to dress appropriately for the occasion, especially since some restaurants and venues have dress codes to adhere to.

The good news is that dressing for date night doesn't require extra work. By following a few quick tips and trips, you can look your best on any date without sacrificing comfort or time.

Dress for the Occasion

When it comes to getting ready for date night, you'll want to dress appropriately for the plans themselves. For example, if you're going to a fancy candlelit restaurant and a show afterward, you should plan on incorporating a suit jacket or men's blazer into your outfit, and potentially a men's tie as well. These touches are a must-have if you have an extra fancy date night planned but aren't necessarily a requirement if you're heading to a more casual restaurant and perhaps the movies afterward, rather than a fine dining establishment and live theatre. As a pro tip, always research in advance to see if the restaurant you're going to has a dress code so you won't be caught off-guard while you're on your date.

That said, even if the date you have planned involves slightly more casual venues, you should still wear a nice dress shirt and bottoms, but maybe skip the blazer and tie. If you're planning a very casual or even sporty date night outing, like mini-golfing or bowling, you can opt for an outfit that's casual yet still flattering and elevated from your day-to-day. For example, don a nice polo shirt and performance chinos rather than a dressy button-down and slacks.

Choose Flattering Bottoms

Now that you know the vibe of the evening, including any relevant venue dress codes, you can start building the perfect look. Any great men's date night outfit begins with a flattering pair of pants. If you're going out for a more low-key evening, you can definitely opt for a pair of jeans if that's what you're most comfortable in. Since your outfit should be elevated from your everyday look, choose a pair of dark blue or black jeans with a flattering fit. Avoid rocking jeans that are too worn out or baggy, even if your evening plans are on the more casual side. If you're going out to a nicer restaurant or event, definitely wear a pair of men's dress pants instead of jeans, like twill khakis or dark blue dress pants with a flattering tailored fit.

Men's chinos are also a perfect date night option. They look just like your favorite dress pants while also being comfortable and super easy to care for. Chinos are often available in styles with some added stretch at the waist and in no-iron materials that are also stain-resistant, making them the perfect option if you want to feel and look your best with minimal effort. Choose a pair of chinos in a fun color, like moss green or vibrant teal, to add a little extra pizzazz to your date night outfit.

Opt for a Snazzy Top

You might not want to wear your go-to comfy tee on date night, as tempting as it may be. Don't worry, it'll still be waiting for you when you get home! Instead, wear a dressy top that's flattering and comfortable, and appropriate for the evening's plans.

If you're heading out on a more casual date night and plan on wearing black or dark blue jeans as suggested above, complete this look with a print button-down shirt that you can wear as-is or layered under a men's V-neck sweater and a pair of dress shoes. Of course, if you're going out to a nicer venue, you'll want to rock some dress pants with a tucked-in men's dress shirt and a blazer or suit jacket, plus a tie if it feels necessary for the occasion.

By following these tips and suggestions, you'll be set for date night regardless of the evening's plans. Always do a bit of research on the restaurants, venues, or other date night stops in advance, and opt for flattering fits and styles, plus materials and fabrics that'll allow you to look as good as you feel.


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