As homecoming season approaches, the air buzzes with excitement, anticipation, and the high-stakes challenge of crafting the perfect proposal. While determining the answer to “what do guys wear to homecoming” is important, figuring out the best way to ask someone to be your date for the evening is what matters most. Whether you’re going for humor or romance, here are some tips from Men’s Wearhouse to ensure a memorable moment.
1. The Classic Sign Ask with a Stylish Twist
Poster board signs are part of many hoco proposal ideas for good reason—they’re personal, photo-friendly, and give you space to show off your sense of humor. The secret to getting that enthusiastic “yes!” you’re hoping for lies in pairing a clever message with an outfit that looks intentional rather than thrown together.
A crisp button up dress shirt in a solid color provides a perfect backdrop for your sign, while chinos in navy or khaki keep the look polished but approachable. The clean lines won’t compete with your poster’s message, and you’ll look put-together in all the photos your family and friends will inevitably post. Consider rolling your sleeves slightly for a more relaxed vibe, and choose shoes that are comfortable for standing around. You might be holding that sign longer than expected.
2. Personal Themed Proposal
Building your ask around something meaningful creates an instant connection and shows you’ve been paying attention. Whether it’s a reference to a movie you both quote constantly, a song that always comes on when you’re hanging out, or a memory from your regular coffee shop, personal touches make proposals memorable.
Your outfit should complement the theme without looking like a costume. If you’re referencing a specific movie or show, subtle nods work better than full character cosplays. A sport coat in the right color or a graphic tee can tie into your theme while keeping you looking sharp.
Consider where you’ll make the proposal and the expectations for homecoming vs. prom proposals. Homecoming tends to be laid-back with more room for creativity compared to prom, giving you more freedom to experiment with themed approaches. Use this flexibility to come up with a hoco proposal that feels like “you.”
3. Match the Fit to the Ask
With some creativity and planning, you can use your outfit to pop the question. This option is great for guys who prefer to let their style do the talking. A graphic tee with the perfect message or an embroidered message on your jacket can turn your outfit into the ask.
Balance is vital with outfit-based proposals. If your shirt carries the message, keep everything else understated. Well-fitted jeans, clean sneakers, and subtle accessories let your proposal shine. Alternatively, you might use homecoming accessories for guys, like a creatively customized tie or pocket square, to spell out your message.
4. Foodie Proposals They Can’t Resist
Food-based proposals tap into everyone’s love for their favorite treats while providing a fun prop to work with. From donut boxes with custom messages to pizza deliveries with special instructions, edible proposals often become the most talked-about asks of the season.
Make sure your outfit complements the casual, fun nature of food proposals without looking sloppy. A Henley or polo shirt paired with chinos strikes the right balance between relaxed and thoughtful. Avoid anything too formal. You want to match the playful energy of surprising someone with their favorite snacks.
5. Group-Ask Game Plans
Coordinating group proposals builds excitement and eliminates the pressure of individual asks. When everyone’s involved, the energy is infectious. Your outfit coordination can range from subtle color matching to full theme coordination, depending on your group’s style.
Deciding what to wear for group proposals requires some careful planning. Choose a unifying element—like the same color shirt—and let individual personalities shine in other outfit elements. This approach allows each person to maintain their personal style while creating visual cohesion in photos.
6. Romantic But Not Cringe
Romance doesn’t have to include over-the-top gestures that make everyone uncomfortable. Thoughtful romantic proposals focus on genuine connection rather than grand spectacles. A handwritten note, her favorite flowers, or a meaningful location create intimacy without the awkwardness factor.
What you wear for a romantic proposal should reflect your sincerity. A button down shirt in a soft color paired with well-fitted dress pants shows you’ve made an effort without trying too hard. Avoid anything too casual or excessively formal. You want to hit the sweet spot that says “I care” without screaming “prom proposal in September.”
7. Seal the Deal with Confidence
Your proposal’s success depends more on your confidence and authenticity than on elaborate planning or expensive outfits. The best hoco proposal ideas are those that feel genuine, show thoughtfulness, and reflect both personalities. When you feel good about how you look, that confidence translates into a more compelling proposal.
Homecoming is about celebrating your school community and having fun with friends. Your proposal sets the tone for the entire experience—from the anticipation leading up to the dance to the memories you’ll create together. Choose an approach that feels true to who you are, and don’t be afraid to show your personality.
For more guidance on putting together the perfect hoco proposal look, learn more about chinos or discover men’s suit accessories to look and feel your best for the big dance.