Gap’s Black Flare Jeans for a Casual Date Night Outfit


2016-01-23 12.18.04

Date night! They seem to be few and far between these days. But Sienna’s preschool had an amazing thing last week…PJ movie night at the school so the parents could have a night off! Brilliant. I vote more of these, for reals.

I’d been wanting to try these Gap Black Flares for a while. I was in the store the other day and Sienna was in a fairly good mood (also strapped into the stroller), so I thought I’d try them out. They are good. They are high rise, skinny through the leg and nicely flared. They didn’t have a petite length at the store, so I got regular, but they are really long. I have hem tape on them here, but I’ll have to hem them soon. And I promise it was sunny when we left the house…

2016-01-23 12.15.14

In the light of day my pattern mixing is a little crazy here…but the night before (when I actually wore this) I really loved it. Hmm. I still think it’s ok though and kinda fun/funky. I also think a dressier black shoe would’ve been good, but, ya know…rain. (Btw, see all that green on the ground? It’s mostly moss. I know. I love it here.)

2016-01-23 12.21.47-2

2016-01-23 12.18.40
I was laughing at Sienna being silly around the corner. Goodness, she is spit-fire these days. The joys of approaching 3 years old. Anyone else exhausted from this age? But it’s so darn cute. Nature does this for a reason.

2016-01-23 12.17.20

2016-01-23 12.18.09
And this bag. I think I’ve mentioned it before, but it’s my favorite, you guys. So good. And the sunglasses are Warby Parker and also great. Check them out if you haven’t tried them. I sadly can’t seem to get the prescription just right on their glasses, but am loving their sunglasses.

Outfit Details

HM Blouse with Standup Collar – Not sure why they don’t have the owl print online, but the yellow print with dancers is so cute. I love this top. It’s great with the high rise jeans because it’s not cropped but hits just at the waistline for me, so the high rise keeps things covered.

Gap 1969 Resolution Destructed Black Skinny Flare Jeans – Really good. Even better when I get them hemmed. The resolution jean is supposed to hold up all day and not stretch out. I found that to be true for the 4 hours or so I had them on. Great job, Gap.

Madewell Transport Tote in English Saddle – Best bag ever. A little big for my short frame, but I love it so much I don’t care. It holds everything and holds up so well. The only problem with it is that I stuff it too full! It really is so well made. They also offer the tote in a black/brown combo that I love.

Soft Surroundings Michelle Boots – These aren’t my exact boots, but those keep selling out and these are SO so close. They look really similar.

Warby Parker Madison Sunglasses in English Oak – Love them. They come in a couple of other colors, too.

Religion Eternal Tailored Wool Coat With Leopard Print Panels – My coat is old Topshop, but I love this one from Asos even more! So so cool.

Shop These and Similar Items for Casual Date Night


What do you like to sport on a causal date night? Fun, dressy shoes are tough in winter, but I want to hear it if you’ve figured out some trick. And here’s hoping you get a date night soon, too!



  1. Laura,
    I have been looking for a new pair of booties for a while now. I think your Emu Austrailia boots are just what I am looking for. Ordering shoes online is s o hard. I have only found two reviews one said they run big and the other said they are true to size. How did they fit for you? Thanks

    • Hi Kate! I found them to run true to size, for me. They do move up and down on my foot a bit, but not in an uncomfortable way and they don’t rub or leave blisters or anything. Maybe that means they run a tiny bit large, but I love the fit of mine. Plus, I can easily wear a bit heavier sock when I want with them. I hope that helps you! I wear mine just about every other day, if that also helps. They are the best!

      • Thanks for responding Laura. I ordered them in the smaller size. I am always between a 7.5 & 8. (I live in South Texas so I don’t really wear thick socks.) I got them yesterday and couldn’t be more happy with the way they look. I wore them around the house to make sure they were right. Today I wore them all day and I love them! They will be my new go to boot! Thanks for the recommendation! I have been following Shana for about five years now I think. I love your style. Glad you joined the team.

  2. Nice post! I especially like your printed blouse suggestions. Super cute.

    I had ordered those Gap resolution black flares online and really loved the fit (except I agree the inseam was so looonnnnggg). I did not, however, love the distressing. On my pair, at least, the distressing looked more like stains and I wished they had a more polished look. Back they went. Boo.

    I got the Gap mid rise authentic flare in black at a super after Christmas sale but those aren’t anywhere close to as soft or stretchy (almost more like a twill) so they sort of give me flashbacks of pants I had in the late ’90’s and I haven’t even taken the tags off.

    So…still on the hunt for a happy pair of high waist black flares!

    • Oh no. Yes, these are so soft and comfy. I would say try the Madewell pair above and see. Some of their jeans are a bit heavier fabric and some are soft and more like the Gap jeans. I haven’t tried this particular pair there, but have been happy overall with their quality and they are nice and dark and would probably have the more polished look you are wanting. Good luck and any good finds, let me know! I’ll keep looking, too!

  3. I totally pull out the BCBGeneration glitter booties that Shana featured a couple years ago for flashy cold weather glam. And I ALWAYS get compliments on them. They totally transform jeans and simple top into date night kapow.

Leave a Reply