What to Wear When Proposing: How to Pick an Outfit for You and Your Significant Other

You’re proposing? That’s exciting! You want everything to be perfect, of course. You’ve got the perfect place in mind, the perfect oval-shaped engagement ring and a photographer hidden. You’re probably already full to the brim with butterflies. The last thing you want is a bad outfit in a photo that you’re going to have forever. If you (or your significant other) need some outfit help on this big day, hey, no worries. That’s what we’re here for. Let’s go over a couple of general rules first.

Element of Surprise

If you buy your significant other an outfit and plan out some unique and special activity, there’s a decent chance they’ll get the hint. If that doesn’t bother you, great. If it does, well, you’ll have to get creative. Maybe get their friends involved. It’s gonna be tough, we won’t lie, but not impossible if you’re wily enough.

Source: shutterstock.com/Syda Productions

When Should You Propose?

Ah, the age-old question: Should I propose before or after dinner? Well, propose whenever you like, especially if dinner isn’t on the table. As a general rule, though, you want to propose sooner rather than later. If you go on a three-hour walk before proposing, you both will be wildly antsy and your outfits won’t be nearly as on point. Propose early and then take plenty of time with just the two of you to decompress after the pictures.

How to Pick Out the Perfect Outfit

You have to pay attention to more than just what looks good, though that definitely is a factor.

Where Are You Going?

If you’re proposing on a mountaintop, don’t buy your girlfriend a ball gown, ya know? Seems obvious, but you want to make sure you’re both dressed for the occasion. Proposals over dinner require a different outfit than proposals at the park. This is the first and probably most important thing you need to consider.

What Will Stand the Test of Time?

Leave those hammer pants on ice. Err toward classic and timeless. Your zoot suit is never coming back into fashion. Stop it. Go simple and dress toward the formal end of whatever the situation dictates. Also, leave the Apple watch at home. Wearable tech does not age well, and we guarantee that photo will look dated within a few years. Wearable tech isn’t hammer pants, but it’ll eventually look like it. You want both your outfits to lean toward classic and away from trends.

Make Sure They Look Good Together

This should be obvious, but the last thing you want is to look like you’re going to two separate events. Sure, both your outfits look awesome, but if you look like you’re going to the Kentucky Derby and he’s headed on an international flight, those pictures will turn out less than ideal.

Source: shutterstock.com/Prostock-studio

Play It by Ear

The element of surprise with planned outfits can be tough. One way to get around this is to have a few outfits of your own ready to go. It’s not unreasonable that your significant other sends you an outfit photo. Maybe you get a friend in on it who relays the outfit to you. Once you know what they’re wearing, you adjust your outfit accordingly and, boom, coordinating proposal outfits.

The caveat here: This may not be a great idea if your significant other is stylistically challenged.

You Don’t Need to Buy New Clothes

In fact, you might not want to. If you pick out a whole new outfit that you feel awesome in, then disregard this advice. This isn’t as much of a concern for the stylish and adventurous. If you have a more conservative style or just aren’t as talented at creating outfits (no shame in it), then a whole new outfit may not make you feel confident. Go with something you know instead of something new that you don’t feel like yourself in.

How Will You Hold the Ring?

This should go without saying, but you need to be able to fit a ring (or ring box) somewhere in your outfit. We hear what you’re thinking. No, this is not us giving you a tacit excuse to wear your cargo shorts. In fact, donate those immediately. Stop it.

Source: shutterstock.com/Syda Productions

Just Look Presentable

Up your style 10-20%. You don’t need to hop into your chrysalis and come out a stylish butterfly, but you do want to dial it up a little bit. Maybe put on a watch or some new heels. Go over your basic grooming one more time, especially if you’re rocking facial hair or a hairstyle where you need a cut every few weeks. You don’t need to be James Bond, but you do want to be a slightly elevated version of yourself.

Sure, it’s not entirely about the outfit. It’s about the love you have for each other. However, do you really want to look back on your proposal photos and realize you were wearing the modern equivalent of hammer pants? With just a little bit of work, this can be entirely avoided.