Fashion Tips for Your First First Date After a Long Break

September 22, 2023

Dating after a long-term relationship ends can be intimidating. You may feel out of practice and uncertain about how to dress for a first date when you haven't been on one in years. The good news is that with some planning, you can pick an outfit that makes you feel confident and comfortable. 

Here are some tips on how to choose a great first date outfit after not dating for a while:

Focus on what makes you feel good

The most important thing is to wear something that makes you feel like the best version of yourself. Think about the outfits that make you feel confident, sexy, and ready to take on the world. Avoid anything that's uncomfortable, doesn't fit right, or makes you feel self-conscious. This date is about you - not impressing your ex or anyone else.

Dress for the date activity/setting

Take the date location and activity into account when choosing an outfit. A dressy restaurant may call for a cocktail dress or dress pants; a casual brewery could be jeans and a nice top. Check the weather too - bring layers if it may get cold. The key is finding a middle ground between dressed up and overly casual. You want an outfit that flatters you while still being appropriate.

Skip the temptation to go overboard

It's tempting after a breakup to go for a big makeover, buy a whole new wardrobe, or wear something wildly out of character. But drastic changes can backfire on a first date, leaving you feeling like you're playing dress-up. Go for an enhanced version of yourself instead of a brand new you. Pick flattering basics with a few trendy accents to feel current.

Don't be afraid to ask for advice

If you feel really stuck deciding what to wear, don't hesitate to ask friends (especially those with great style) for their input. Share a few outfit options and ask which they think would be best for the date. A fresh perspective can help you identify the most flattering, appropriate choice.

Accessorize strategically

Accessories are a great way to update classic date looks. A stylish jacket, handbag, jewelry, or shoes can make basic pieces feel fresh and new. Scarves, bold lipstick, or a pop of color in your accessories can also give your look a current vibe.

Feel fabulous under the clothes too

Pretty underthings or lingerie can make you feel sexy and confident, even if no one else catches a glimpse. Treat yourself to some nice bras, panties, shapewear or stockings in fabrics and styles you love. Feeling good underneath can boost your confidence exponentially.

Plan ahead (and have a backup)

To avoid any date day drama, start getting outfits together a few days in advance. Try things on and check the full look in the mirror. If you don't love it, rework it until you feel great. Picking out shoes and accessories ahead of time helps too. And pack a backup outfit in case of spills, stains, or sudden weather changes.

Remember - first date outfit don't have to be perfect

First dates are about making connections. What you wear is far less important than being authentic, laughing, and having fun. The goal is to feel comfortable being yourself. So don't obsess over finding a perfect outfit - a go-to date look you feel great in is more than enough.

Getting dressed for your first first date in years can be a little intimidating, but also exciting! Focus on choosing pieces that highlight your best features, suit the date vibe, and make you feel like the beautiful, confident woman you are. With the right outfit, you'll be ready to make a fabulous first impression and have an amazing time rediscovering the fun of dating.

Here are some examples of great date looks to inspire you:

  • Little black dress with heels and a leather jacket
  • Dark jeans with a silky camisole, blazer and booties
  • Faux suede skirt with tucked in graphic tee and sandals
  • Palazzo pants with an off-the-shoulder top and wedges
  • Fitted sweater dress and tall boots
  • Wide-leg jumpsuit with strappy heels and long earrings

The most important thing is that YOU feel happy and comfortable. So relax, be yourself, and wear something that puts an extra boost in your step. You've got this! Now get excited for a wonderful first date.

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