What to Wear for a Fun Night Out on the Town

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Date night, girls night out and other evening event fashion and outfit ideas, especially for women over forty!


I had so much fun putting together this post. It is definitely a bit outside our normal over forty/conservative-ish fashion parameters but the hardest time to figure out what to wear can be with evening or special events. Most of us have some sort of a daytime uniform like cardigans, jeans and boots in the fall, or a sundress in the summer but an event in the evening can be the great unknown.



I timed this post intentionally since I am heading out to my high school reunion this weekend.  I have been putting together outfits to pack, texting with my high school girlfriends about the dress “code”, and doing way more online shopping than I usually do in honor of this weekend. For some of you, the thought of this kind of event probably makes you break out in a cold sweat, but I was fortunate to have gone to a great high school with a really close group of kids. I still get together every fall with my eight besties from high school (see our pic below at a Virginia winery last fall, that’s me in the crazy long scarf!) and much of our class is still in some sort of touch. My high school was a smaller public school just outside Washington DC in Arlington, which makes for a fun location to get together every decade to catch up.

Our event is taking place in a bar, so it’s not too dressy unlike other reunions. I actually didn’t feel pressured to find anything special to wear but I had fun going through my closet to put some outfits together for the sake of this post and for packing purposes. Being in the ‘middle of life’ as I like to say, fashion can be kind of a gray area, but I think something like this is a great time to wear something fun.

The outfits I picked are definitely a little edgier than I’d probably wear in my quieter, smaller town, but I think they are perfect for a city night out. There are plenty of similar events–a concert, an evening work event, a business trip, even holiday parties that these elements would work perfectly for. Really they are just basics put together in a way that takes them up a notch or two. None of the elements are expensive and all are things that can work with other pieces at other times.


black top   | snake print pants |  similar boots |  purse |  earrings |  necklace

I actually haven’t even picked an outfit for either night — so please let me know which one of these you all like the best in the comments! Above is one of my top two contenders. I did splurge a bit on these snake print pants because they are SO in style this year (though now they are on sale!). I figured if you can’t wear pants like this for this kind of event, where would you? They are so fun! I paired them with a simple black silk top since the pants are enough of a statement. I love them with the gray accessories, these are such great basics that I have gotten so much wear out of. A sidenote is that I haven’t shopped at Express in years but found them (the tops and earrings came from there) to be a great resource for ‘night out’ clothing, I guess have been missing out!


top  |   jeans  |   purse   |   booties (similar)  |   belt |  necklace or here

This is outfit is my other top choice.  I feel like I’d be really comfortable wearing this. I recently splurged on these jeans and have to say how much I love them. AG Jeans are expensive but they are so comfortable it’s not even funny. I went with a straight leg this time instead of skinny which is different but I think it will be great with boots this winter. You can find AG Jeans on sale here right now too.

OK, which outfit do you like better?


white blazer  |   snake pants   |  similar booties  |   camisole   |   necklace

I think these outfits are a bit dressier than I need to be, but a blazer is a great way to dress up at night. I have gotten a ton of wear out of this basic white blazer and it’s one step up from a cardigan for evening. I paired it with a silk camisole (tons on sale here). Which one do you like better, the snake pants or with the jeans below? I like both!



One more to share that is a no-fail, looks good on all body types, outfit idea for you. This tunic top is one everyone should own, and the leather leggings kick the whole outfit up enough to make it a great night out outfit. The top is long and loose so it hides a multitude of sins, and the tighter legging style pants paired with heels will elongate your legs.



leather leggings |  roll tab tunic |   bralette  |  shoes  |   necklace

For a little more night time look I just added this crystal necklace (my birthday gift from Christy! She has such good taste doesn’t she?)  and a bralette under it. I mean I wouldn’t wear this outfit to grocery shop but to a nice restaurant or a work party, this would be a great option.

Also, I would wear a leather jacket over an outfit like these (I’ll probably wear my black one) but this one is a great deal right now. 

Here’s a quick rundown of all the links. I will try to post some actual pictures on IG stories of these outfits on (and what I picked to wear) but let me know what you think! You can shop sources below~



small-amy-new-headshot-summer-2016-2 copy

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  1. I need a couple new Holiday outfits that can be dressy casual and these are all fabulous options. I love them all. I think I like the snake pants outfit for the reunion as #1 then the black wrap top and jeans as #2. Have fun, can’t wait to see the pics.

  2. Love your posts! I think the link to the teal tunic top is broken. It’s cute and I’d love to see where to buy it!

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