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


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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…

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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.)

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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.

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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!