Going on a first date is nerve-wracking at any age, but when you’re in your 50s, things seem especially high stakes.
After all, you’re not getting any younger. Plus, chances are, both you and your date have been around the block a few times when it comes to relationships, and you’re not keen on wasting your time. You want to put your best foot forward and make a good impression, and part of that does come down to how you present yourself. What you wear can make all the difference when it comes to what someone thinks of you, so if you’re unsure what to choose when meeting up with a potential romantic interest for the first time, these are some good rules of thumb to follow.
1. Choose clothes that fit well.
Fit is everything when it comes to looking polished. Wearing clothes that are too loose or too tight can make you appear less put-together. As we age, it’s natural for our bodies to change, so it’s worth investing in tailored pieces or updating your wardrobe to ensure everything fits comfortably. A well-fitted blazer or pair of trousers can elevate your look instantly. If you’re unsure about fit, visit a tailor or try brands that offer sizing for older men. Feeling comfortable and confident in your outfit will show, helping you relax and enjoy the date.
2. Keep it age-appropriate but modern.
Age-appropriate doesn’t mean boring or outdated. It’s about finding a balance between classic style and current trends. Opt for timeless pieces like a button-down shirt, a casual blazer, or a pair of dark jeans. Avoid overly trendy items that don’t suit your personal style, but don’t shy away from subtle modern touches. Adding a contemporary element, like a pair of stylish loafers or a modern watch, can show that you’re in tune with the times without trying too hard. The goal is to look effortlessly stylish while staying true to yourself.
3. Dress for the occasion.
The venue or activity of your first date plays a big role in what you should wear. A casual coffee date might call for a smart-casual look, while a dinner reservation at an upscale restaurant will require something more formal. Dressing appropriately shows that you’ve put thought into the date. If you’re unsure about the setting, err on the side of slightly overdressed rather than underdressed. A collared shirt, nice trousers, and clean shoes can work for most scenarios. You can always adjust your outfit by removing a blazer or rolling up your sleeves to make it more relaxed.
4. Invest in good shoes.
Shoes can make or break an outfit, and they’re often one of the first things people notice. Scuffed or outdated shoes can detract from an otherwise polished look, so it’s worth investing in a quality pair. Classic leather loafers, polished oxfords, or clean trainers can all work, depending on the vibe of your date. Make sure your shoes are clean and well-maintained. Pairing good shoes with a thoughtfully chosen outfit shows that you pay attention to details, which can leave a lasting impression on your date.
5. Stick to neutral colours.
Neutral colours like navy, grey, beige, and white are flattering and versatile, making them a safe choice for first dates. These shades are easy to mix and match, creating a cohesive look that doesn’t feel too busy or overwhelming. That said, adding a subtle pop of colour, like a patterned shirt or a bold tie, can showcase a bit of personality. Just avoid going overboard with bright or clashing colours — it can really distract from your overall look. A balanced palette shows confidence and sophistication.
6. Avoid wearing anything too flashy.
While it’s tempting to dress to impress, overly flashy outfits can come off as trying too hard. Loud patterns, excessive jewellery, or anything too bold can overshadow your personality and make the date about your clothes rather than your connection. Instead, focus on understated elegance. A nice watch or a subtle accessory can add character without being overwhelming. The goal is to look stylish and confident, not like you’re competing for attention.
7. Pay attention to grooming.
Grooming is just as important as your outfit. Neatly trimmed hair, a clean-shaven or well-maintained beard, and fresh breath all contribute to your overall appearance. Even the best outfit can fall flat if grooming is overlooked. Take the time to prepare before the date. A quick visit to the barber, using a high-quality aftershave, or simply ensuring your nails are clean can make a big difference. Grooming shows that you take care of yourself, which is always attractive.
8. Wear fabrics that are comfortable and breathable.
Comfort is key, especially on a first date where nerves might already be running high. Choosing breathable fabrics like cotton, linen, or lightweight wool ensures you stay comfortable throughout the date, whether it’s a warm summer evening or a chilly winter outing. Uncomfortable clothes can make you fidgety or distracted, which might affect how you come across. Feeling at ease in your outfit allows you to focus on the conversation and connection instead of worrying about how you look or feel.
9. Avoid graphic tees or overly casual items.
While casual dates might not require formalwear, items like graphic t-shirts, overly baggy jeans, or worn-out trainers should be avoided. These pieces can make you look like you didn’t put any effort into your appearance, which might send the wrong message. Instead, opt for casual but polished alternatives, like a plain polo shirt or a fitted jumper. These choices strike the right balance between comfort and style, showing that you’ve taken the time to present yourself well.
10. Accessorise thoughtfully.
Accessories can elevate your look, but it’s important not to overdo it. A stylish belt, a classic watch, or a subtle pocket square can add a touch of sophistication to your outfit. Avoid piling on too many accessories, as it can make your look feel cluttered. Choose pieces that complement your overall style and the tone of the date. For example, a leather strap watch pairs well with a casual blazer, while a silver or gold bracelet can add a sleek touch to a dressier look.
11. Check your outfit for details before leaving.
Even the most carefully chosen outfit can be undermined by small details like wrinkles, stains, or loose threads. Taking a few extra minutes to inspect your clothes ensures you’re putting your best foot forward. Little things like ironing your shirt or shining your shoes can make a big difference. Before heading out, do a quick once-over in the mirror to check for any last-minute fixes. These small efforts show that you’ve put thought into your appearance, which can leave a positive impression on your date.
12. Dress for the season and weather.
Wearing the right clothes for the weather not only keeps you comfortable, but also shows that you’re practical and prepared. A lightweight jacket for a spring evening or a stylish coat in winter adds functionality to your look while keeping you appropriately dressed. If the forecast is unpredictable, layering is a smart choice. A well-fitted cardigan or jacket can be added or removed as needed, ensuring you’re comfortable without compromising style. Being prepared for the elements shows thoughtfulness and adds to your overall charm.
13. Avoid overloading on aftershave.
Wearing aftershave can enhance your presence, but too much of it can be overwhelming. A subtle, well-chosen scent adds an attractive touch without being overpowering. A couple of sprays on your neck or wrists is usually enough. Choose an aftershave that suits your style — something fresh and understated tends to work well. Don’t apply too much or mix multiple scents because that can distract rather than enhance your overall look.
14. Let your personality shine through your style.
While it’s important to dress appropriately, your outfit should also reflect who you are. Your personal style is a great way to show your date a bit about your personality. Whether it’s a unique accessory, a favourite colour, or a signature jacket, let your style say something about you. Authenticity is key. When you feel comfortable and confident in what you’re wearing, it shows. Your date will notice the effort you’ve made, while also appreciating that your outfit feels natural and true to who you are.
15. Smile and carry yourself confidently.
The best accessory for any outfit is confidence. A genuine smile and good posture can make any look more appealing. How you carry yourself often leaves a stronger impression than what you’re wearing. Take a deep breath before your date, stand tall, and walk into the room with confidence. When you’re comfortable in your own skin, your outfit becomes part of a bigger picture—one that’s inviting, self-assured, and attractive.
