Date Night Outfit


Now that I’ve re-entered the world of dating (“I feel like I should send you to Chicago with a warning sign…” -my mother) I’m once again facing the age-old “what to wear?” dilemma. Do you have a go-to date night outfit…? I would love to hear! I usually spend 25 minutes on my makeup (smoky eyes, bold brows…) and all of 5 minutes getting dressed. Most nights I sport a variation of the tomboy ensemble above…

1. Black Blazer – This Helmut Lang number is on my wish list, but I usually sport a sharply cut Club Monaco blazer, always unbuttoned or draped over the shoulders… // 2. Eberjey Bralette – I love itty bitty bras like this… // 3. Tai Stick Earrings – I really don’t wear much jewelry, these little studs are subtle and chic… 4. Linen V-Neck Pocket Tee – I have a drawer full, I think the deep V is sexy, I love the grey and the white… // 5. Black Toothpick Jean – some pairs with ripped knees, some without… // 6. Essie ‘Wicked’ Nail Polish – I know it’s spring, but I like my mani dark… // 7. Rag & Bone Harrow Booties – I’ve worn these just about every day since landing in Chicago. They give me some serious height, but you can walk in them for miles… // 8. (not pictured) a yummy scent like Tokyo Milk’s Tainted Love… //  


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8 comments on “Date Night Outfit

  1. ashley

    loving this! another option is to swap out the tee for an interesting longer top, tunic-y? i dont like the bulk of sleeves under a jacket so i would do a sleeveless longer top with an interesting detail, asymmetrical cut or maybe a silky fabric to stand out against the jacket and jean/leggings. also LOVE the dress over pants thing. works very well with a jacket topper for sure

  2. Catherine

    I’m not dating but this is my go-to going out outfit. It’s perfectly relaxed for bars and if you end up going dancing, you don’t look too try-hard either. I wish I could get away with little lace bras like this though!

  3. Jackie

    Hi Katie! Love that you posted this, because I recently re-entered the dating world as well. I had a similar outfit going on, but one guy told me you can never go wrong with a little black dress – always a winner. As much as I resented him for expressing this, I felt like it was good advice. I try to push myself to be a little more girlie with a flirtie outfit. I think the above is perfect for colder weather, but in the summer I would swap out that tee for a slinky silk spaghetti strap. Just a thought from one single gal to the next :)

    Love your posts! And good luck with dating! (Feel like Chicago would have some solid candidates!)


  4. Lauren

    Love this, Katie! I painted my nails black again last night after forcing a lovely shade of pink on them last week for spring but my heart just wasn’t in it! It’s great to know I’m not the only one! Thank you! Congrats on the move and enjoy every second!

  5. Alison @ Peacoat Diaries

    I love this outfit and have worn variations of it myself, but I think this is the kind of look that is most successful at impressing other women. Other ladies will see you and will totally dig the smoky eye, the sleek lines…but in my experience, dudes don’t necessarily appreciate that kind of stuff. But you have to be comfortable and feel like yourself — so if this is it, go for it!

  6. Kiri

    A cute bra is a must for me. If I am feeling sassy underneath my clothes it gives me that hidden boost of confidence. More important than anything is to have fun. When I met my now husband I had no idea it would be my last first date. I wish I had enjoyed the butterflies a bit more!

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