Reader Question

I am 47 and started dating again and I am really at loss as what to wear to my dates. I found your suggestions about what to wear on the first, second and third date. I love them. Dresses for date #2 and #3 are perfect for a really nice restaurant, however, I would like to know what to wear if I am going just to a local low key Mexican or Indian restaurant, or to museum. Could you please, suggest something that does not include jeans, since I really don’t like wearing them.

Wardrobe 911’s Style Prescription

There are usually only two reasons for why someone doesn’t like to wear jeans:

1. They haven’t found a pair that looks good on them that they like, or
2. It’s because they are a polished chic kinda gal who doesn’t do jeans

The answer is critical to what my advice to you would be so I’m going to assume the later and style your outfit based on what I know about the gal that doesn’t do jeans.

If you find yourself in a store these days, you’ll be hit with few options for nice pants that aren’t for work.  The casual ones are unfortunately either harem (eek!), sequined (ack!) or frumpy (no!)  — not what you want to wear on a date.

Luckily, there are a few that are hiding in the racks that would work well and one of them is the Theory Enosa knit pant.  It is sleek, thick and comfy yet casual and elegant. Calvin Klein and Diane von Furstenberg also have pants made out of this material this season and it’s a great option to jeans.

Keep it casual with a simple, yet still a tiny-bit-feminine, black ruffle tank.  The ruffles are low-key and will subtly peek out from underneath this hourglass-perfect camel sweater. Add an interesting, bold pearl necklace or a long necklace to create a more casual-elegant vibe.  You’ll definitely want to add some sex appeal with these high-heeled suede booties by Stuart Weitzman (they go to 10.5.)

For other date outfits, check out:

• Movie Date
• Work Lunch Date
• Park Date