The Brook Taverner Journal

What to Wear When Proposing?

Finding the perfect person you want to spend the rest of your life with isn’t always easy. Sometimes you fall in love with your primary school sweetheart and ask them to marry you right after graduation. Other times you have to wait, searching for the one through a sea of prospects who are just not quite your happily ever after.

When the time finally comes for you to get down on one knee and say those four special words, it’s important that you’re completely ready. Not only do you need to know exactly what you’re going to say and have the right ring, but you also need to make sure you’re wearing an appropriate ensemble for the occasion.

So, how do you choose the right thing to wear when you’re proposing? Here are a few tips that will help make your sartorial decisions a little easier.

What to Wear to Propose

The truth is, where you plan to propose greatly affects what you wear. If you’re outside-the-box thinker, you may not be able to wear a traditional suit and tie to your proposal. Let’s take a look at a few different scenarios and the attire that works best for them.

Proposal Scenario 1: The Restaurant

One of the most traditional ways to propose is in a nice restaurant. Maybe you’ll hide the ring in a glass of champagne. Maybe you’ll get down on one knee right before the desert arrives.

At a restaurant, the first thing to remember are to never hide the ring in food. If they can’t see it, they’re likely to swallow it. Second, don’t suddenly spring a nice restaurant on the one you’re proposing to. If you’re taken them to nothing but fast-food places for the last five years, they’re going to be suspicious. Build up to the proposal.

When deciding what to wear at the restaurant, consider the dress code as well as what you’ve worn to restaurants like this before. If you normally wear a black men’s suit with a pair of oxford and a tie, she won’t be suspicious that you’re wearing one this time. If you normally wear a pair of chinos and a tee, however, her internal alarm is going to go off.

Dress as you normally do when you go on a date to a nice restaurant. You can touch up the details a little, changing the pattern of your suit jacket or trading in a tee shirt for a dress shirt, just don’t make too many changes.

Proposal Scenario 2: Destination Proposal

If you plan on proposing to your one and only and you’d like to dress to the nines for the occasion, consider asking her to meet you someplace or having someone else bring her to you. Since she won’t see you before this time, you can dress the way you like. We recommend going all out in men’s suits. You can even wear a tux if you want to.

For this situation, make sure she’s wearing something that will compliment your outfit as well, just in case the two of you decide to do something together after the proposal. If you’re wearing a tux, for instance, you can tell her that you’ll both be attending a black-tie charity event. This will help ensure she dresses for the proposal in such a way that compliments your attire. If she doesn’t have a dress in her wardrobe that will work for such an occasion, make sure you tell her well ahead of time so she has time to pick out the dress she wants and be prepared for the event.

Proposal Scenario 3: Country Life

There are so many different ways you can propose to the one you love. If you both love the country, you can ask her to marry you at the top of a mountain after a long hike, on the back of a horse after a beautiful ride through flowery fields or even in the middle of nowhere over a picnic meal on the grass.

For these types of proposals, a suit is a bit much. Instead, embrace your country roots and consider wearing tweed. A tweed jacket over a dress shirt, along with a pair of trousers or jeans provides a smart, yet casual look ideal for country proposals.

What About Her?


No matter where you want to pop the questions, always make sure you think about how she’s going to look, as well as yourself. Today, most couples take pictures after their proposals and post them to their social media sites online to let everyone know about the happy event. Someone may even be willing to take pictures for you while the proposal is happening.

While pictures are important, she isn’t going to like those photographs nearly as much if she looks grungy or like she just left the gym and didn’t have a chance to change her clothes yet. Let her know that something is going on (without giving away the fact that you’re going to ask her to marry you) so that she is ready and dressed. She doesn’t have to look perfect, but it’s going to be important to her that she looks nice.

In addition, you need to think about her and her possible reactions to the proposal. You may have it planned on the beach, but she only wore high heels instead of sandals. You might be planning to drop to one knee at the exact spot you first saw her, but because it’s outdoors she doesn’t want to take a walk with you to that location. She’s too cold, and she didn’t bring her jacket with her because it clashed with her clothes. Be prepared for anything to happen.

Are you ready to say those important four words that will change your life forever? Make sure you’re wearing the right clothing when you propose. The right attire will inspire happy, beautiful memories you’ll talk to your children and grandchildren about for years to come.

By Brook Taverner