Not sure what to wear on dinner dates? Well you’re not the only one.

Tackling Challenge 5 is a bit tough, because much of it has to do with personal style, comfort levels, where the date is taking place and with whom. (First date with a new person or date 126 with your significant other?) So there’s no one-size-fits-all-answer.

That said, I’ll do my very best to help you navigate this (sometimes) tricky event. First I’ll start off with some suggestions and then provide you with a few outfit examples that’ll hopefully trigger some ideas for your next big night out.

Challenge 5: Dinner Date


Suggestion 1: Look and Feel Amazing

I’m going to assume that a dinner date is just that – a date. And regardless of how long you’ve known or have been with this person, a date is a date. And you should look and feel amazing. So wear something that accomplishes that.

Also, make sure that you’re comfortable in whatever you choose. And that you won’t have to worry about wardrobe malfunctions. Nothing’s more distracting than you fidgeting or fussing in your clothes.

Suggestion 2: Turn on Your Sexy

What woman doesn’t like to feel a little (or a lot) sexy? Especially on a date.

That said, it doesn’t have to be overt. Everyone’s definition of sexy is different. For some, putting on some sexy lingerie does the trick. For others it might be showing a little extra skin, wearing something silky or lacy, or putting on a pair of killer heels.

The most important thing is that you feel like the hottest hottie you are. Confidence on a date is everything.

Suggestion 3: Complete Your Look

Yesterday I wrote about accessories and how they pull your whole outfit together. I also mentioned hair and makeup and how they can make or break what you’re wearing. All three of these, together, complete your look.

Don’t go through all the trouble of putting on the best of your best and have it all fall apart at the very end.


Example 1: Little Black Dress

I’m a huge believer in dressing for dinner – no matter where I go. What could be easier than throwing on a little black dress, a pair of heels and a few accessories. Instant outfit!


Example 2: Romper

Not a huge fan of dresses? Rompers are another super easy way to throw an outfit together. Some are dressier than others, so choose and build your look accordingly.


Example 3: Skirt and Blouse

Skirts and blouses provide a ton of flexibility and options (the mixing and matching possibilities are endless) while still maintaining a “dressed” look.


Example 4: Pants and Blouse

Pants and blouses (or shirts) provide the same flexibility and options as the skirts and blouses example above. Make your look as dressy or casual as you’d like.


Example 5: Jeans

Not up for being overly dressy? You can still create a fabulous look with jeans. Consider where you’re going and choose your accompanying pieces accordingly. Finish off your look with fab accessories, some hair and makeup and you’ll be good to go!