Clothes are more than fabric; they signal identity, mood, and intention.
Choosing outfits that make you feel attractive, comfortable, and authentically yourself can help rebuild your sense of self-worth after the end of a long-term relationship and project confidence in new dating situations. Whether it’s a sharp blazer, a favorite dress, or a casual look that feels effortlessly you, dressing with intention communicates readiness to step into a new chapter.
Declutter and change up
Clinging to an outdated wardrobe can sabotage your dating mindset. Wearing clothes that remind you of your past relationship, that no longer fit well, or that don’t reflect who you are now can reinforce feelings of insecurity. You might unintentionally downplay your presence or feel like you’re hiding instead of showing up fully.
Dressing should energize you rather than feel like a hassle or a chore. Say goodbye if it’s worn out, doesn’t fit, or hasn’t been worn in the past year. Review clothes that are years old and might not reflect the person you’ve become.
Quality should always take precedence over quantity. You can mix and match timeless basics like a versatile blazer, a pair of jeans, and a little black dress and dress these essentials up or down.
Identify what makes you happy and confident
Think about what makes you feel confident and happy, not only in the context of dating after divorce but also in general. Are you more conservative, edgy, classic, fashion-forward, casual, or a combination of styles? Your closet should mirror your lifestyle and personality.
Add statement pieces and a personal touch
Items like a statement jacket, a funky accessory, or a bold print will lend your wardrobe a unique flair. They add a story to your style, whether it’s a custom-made piece or a vintage scarf from a trip, as long as it doesn’t remind you of your ex.
An organized closet makes getting ready for a date much easier. Arrange your clothes by type – i.e., pants, tops, shorts, shirts, etc. – and then by color.
Comfortable clothes empower dating
Respondents in a recent survey were asked to rate how comfortable they felt on first dates after meeting someone online. Very few respondents said they were “extremely comfortable” on a first date, but 37.7% rated their comfort level as high (4 out of 5), and the result was quite similar for women and men. The rest of the respondents, a majority, rated their comfort level as 3 or below.
The connection between comfort and clothes is worth exploring. Dressing in ways that feel unnatural creates discomfort. When clothing doesn’t align with our true feelings, it creates tension. Evidence suggests what we wear affects our confidence. For instance, flight attendants rated themselves more professional and competent in uniform than in their own clothes, although the job was no different. Clothing helps embody traits like belonging, competence, and confidence, which spill over into dating and affect the potential outcome.
The bottom line
Many women today just want to be comfortable after centuries of painful fashion trends. A late 2024 survey found that 66% of UK women considered fit to be the most important factor affecting their confidence, while over half prioritized comfort over trends.
Another survey revealed that millennial women were likelier than millennial men to put comfort over price. The majority of women said they valued comfort as much as durability and quality, while men valued durability and quality more than comfort by 10%.
Dress comfortably on your first date and any subsequent ones. Fretting over an outfit that’s too tight, too loose, or otherwise ill-fitting takes away from being present and mindful, and it can sabotage the date despite your good intentions.
