TL;DR: Ripped or shredded jeans, sky-high stilettos, graphic T-shirts, crop tops, TikTok or Instagram beauty trends like extremely heavy or overly sparkly makeup are examples of poor choices.
Reentering the dating pool can be unsettling. You’re not as young and carefree as you were in your 20s, and the dating world is a different place. If you’ve been single for some time, you’ve probably received a pile of unwanted dating advice. The pressure to look young pushes people in their 40s or 50s toward trends that prioritize youthfulness over authenticity or comfort.
Instead of embracing styles that reflect their personality and life experience, many feel compelled to adopt clothing that mimics younger generations, fearing that age-appropriate attire might make them seem undesirable or out of touch. This anxiety can lead to awkward or inauthentic fashion decisions that undermine confidence rather than enhance it, creating a disconnect between personal identity and outward appearance.
When trying too hard becomes obvious
Ripped or shredded jeans may be trendy among younger people, but on an older adult, they can come off as trying too hard or appear out of place, especially when paired with garments like crop tops or graphic tees.
Some older women might opt for sky-high stilettos, thinking they add glamour, but they often sacrifice comfort and practicality, drawing attention for the wrong reasons.
Mimicking TikTok or Instagram beauty trends like over-contoured faces, bubble braids, or pastel-colored hair can appear unnatural on mature skin and features.
Wearing flashy, overly sparkly tops or makeup that’s more suited for a nightclub can seem like an attempt to cling to a younger party persona.
No need to turn back the clock
Overreliance on fashion trends is a common pitfall of dating after 40, as if dressing like you’re in your 20s will magically transport you to that decade. It won’t, and what’s more, there is no need. Once one realizes how much they have learned and how far they’ve come, avoiding dating pitfalls after 40, like dressing like a much younger person, will get much easier.
Confidence is definitely an issue for many of those reentering the dating pool, as the likelihood of a positive self-image seems to decline with age. Around half (50.6%) of 16-24-year-olds often worry about what others think of them, according to a recent survey. This percentage goes up to 80% for those aged 35-54 who said they didn’t feel confident, especially in their appearance. Finally, just 10% of people over 45 think they are attractive, leaving a whopping 90% that don’t.
Society is paradoxically obsessed with maintaining youth, considering aging is probably the most natural and inevitable part of life. The pressure to look younger is sky-high; we are bombarded with images of wrinkle-free, flawless people at every turn. Why are people vulnerable to the pressure?
We want to feel, not only look young
Aging brings resilience and wisdom but also challenges like loneliness, grief, and a shifting sense of identity. As children grow up and relationships evolve, many find themselves reevaluating their life purpose and coping with new emotions. We want to feel young and carefree again, and efforts to appear youthful reflect this deeper need.
Instead of focusing on appearance, it may help to shift attention to other dating pitfalls that also need to be avoided, such as an unwillingness to try new things, being deceptive about one’s identity, and going for someone who’s like an ex. Embrace original dating ideas like an evening at the aquarium: unique dates are excellent icebreakers and a great way to find out more about someone than chatting at a restaurant or cafe.
If you’re going to use dating apps, you might be tempted to use an outdated picture or leave off important information from your profile. It’s as true as ever in 2025; you can’t connect with someone genuinely if you aren’t honest. There’s always a reason why your ex is your ex. If a potential partner is displaying similar behavior to a previous one, take measures to keep history from repeating itself.
