What to Wear to an Anniversary Party or Dinner

For some people, fashion just doesn’t register. You may have the same uniform of jeans and a t-shirt daily, or maybe you’ve got five different versions of the same outfit in your closet to get you through the workweek.

But rest assured that picking out the right outfit for a special occasion can be a lot of work even for the most devout of fashionistas. So when you’re attending an anniversary dinner or party, what should you wear? Don’t worry, we’re here to help!

Location, Location, Location

Many times, wardrobe decisions will be made for you based on where you plan on going. Look up the venue—whether it’s a restaurant, club, or an event hall—and see if they’ve got dress code on their website. If they require a jacket and tie for men, boom! You’re set. Suit and tie it is, or dress and heels (or nice flats or sandals!) it is.

If it’s the fanciest of fancy, there may be more required. But if a tuxedo is required, you’ll definitely be made aware—besides, how often will that happen? Pretty rarely. What if there’s no dress code specifically listed? Take a look at the pictures on their website. It’s not foolproof, especially if you’re having a party at an hall that hosts all sorts of events, but their site may clue you in to the wardrobe that’s expected.

What to Wear to an Anniversary Dinner

If it’s just the two of you, it’s very possible you’ll be going out to one of your favorite places for dinner, and it may be on the casual side. That doesn’t mean you should treat the dinner like it’s just another night out.

A good rule of thumb for celebrating a special event like an anniversary or birthday is to dial your wardrobe up a notch from what you’d normally wear to the same place. If you’d normally wear shorts, wear long pants or a skirt. Jeans are usually a little too casual for a special occasion, but there may be exceptions to this rule.

If you don’t have clothes formal enough for the evening, there’s no harm in borrowing something from a friend for a day. If you’ll only wear it once, there’s no reason you need to own it forever. Still, when in doubt, for almost every occasion, it’s better to be overdressed than underdressed.

You can also reverse-engineer this by picking out what you’d like to wear—it’s likely you’ll want to commemorate the night with a selfie, at least!—and find a restaurant that matches. If one of you wants to wear their best dress or a suit and tie, you’ve effectively picked how nice a restaurant you’d like to go to…which is not to say you can’t go out for fast food in your fanciest outfits.

It might be fun, especially if the location has special meaning to you and your significant other. The bottom line is that you and your sweetheart should both wear something that makes you special, and helps you mark the special nature of the day.

What to Wear to an Anniversary Party

What if you and your sweetheart are celebrating a milestone anniversary and you’re having a party to celebrate? It doesn’t necessarily make picking out what to wear any easier just because you know it’s a party. The number of people there, the venue, and other factors are better determiners.

If you weren’t the one to plan the party, ask the person who did. In most cases, your significant other did (or “both” of you did and you just weren’t paying attention!). Ask your sweetheart what’s appropriate to wear. They may have a favorite outfit of yours that they’d like to see you in. Or ask what they plan on wearing and pick out something with a similar level of formal or casual. And while it’s not common, people occasionally have themed or costumed anniversary parties.

This isn’t common, and you’ll most certainly find that information out beforehand, but themes and costumes can actually take off a lot of the pressure because you’ll have a clear guide of what’s appropriate (In fact, if you’re still in the planning phases and like to do things a little off the wall, you might want to suggest a theme!).

Still, a party is almost always at least a little bit fancier than just the two of you at dinner, so keep that in mind. You should shave and have a fresh haircut no matter how casual the event, but you’ll want to step it up a little bit for a party.

Take some extra time styling your hair and shine your shoes. You can never go wrong paying attention to the little details. But no matter how fancy the party, make sure you’re wearing something you’ll be comfortable in for several hours.

You and your sweetheart will be the guests of honor, so while being photo-ready is important, you also don’t want to wear something so tight or heels so high that you’ll be miserable the whole night—remember, you’re supposed to be enjoying the night!

It’s Not Just What You Wear…

…It’s how you wear it. It doesn’t matter how fancy or casual the anniversary celebration is, you should treat it like the special occasion it is and wear clothes that are clean, with no rips or stains. (Feel like that’s common knowledge? You’d be surprised.)

And be ready to break out the iron: your clothes should be wrinkle-free, too. If that seems like it’s beyond your abilities, that’s okay. It’s a good life skill to have, but for a celebration, getting it right is actually more important than learning how to do it yourself. A dry cleaner or laundromat will almost always have a laundry service that will be able whip your clothes into shape.

The important thing is to show that you’re taking the celebration seriously. Other than that, be creative, have fun, and celebrate your special day!

Photo of author

Author: Matt Seymour, MSF

Matthew J. Seymour is a dating industry expert with over a decade of experience coaching singles, reviewing dating apps, and analyzing trends within the industry. Matt is a published author with his most recent work “Get More Dates: How to Master Online Dating Apps” that hit shelves in 2023. With a Masters of Science in Finance (MSF) degree from the University of Florida and extensive knowledge of the innerworkings of the online dating industry, Matt frequently serves in an advisory role to some of the largest dating apps on the market. In Matt’s current role with Healthy Framework, he leads the interview team that regularly interviews key dating industry leaders, and leverages his financial knowledge and dating app experience to review and share what singles need to know to get the most out of dating online.