What I Wore — A Millennial’s Guide to Night Out Looks: From a Little Black Dress to Pink Power Dressing, and Much More

It’s one of life’s perennial problems; a loaded question to which there is rarely a straight answer.

You can try to dodge it when somebody asks you, but sooner or later you’re going to have to ask yourself.

“What are you wearing tonight?”

I’ve spent too much time trying to come up with a decent answer. I could, like, learn another language or much-needed life skill if I cared less about clothes. Clearly I don’t, so let’s talk outfit planning.

I’m not really a plan-ahead kind of girl, but having some basic outfit recipes on file has helped expedite my getting ready process.

To be honest, I’ve had full blown meltdowns over having nothing to wear and if you haven’t, congratulations, that’s really chill of you. Everybody else, gather ‘round for some questionable style advice.

A couple months ago, I made my fashion blogging debut to show you all what a week in work outfits looks like to me. This time, I hit the town with five night-out looks. I hope these give you some inspiration or ideas.

The LBD

You can’t go wrong with a little black dress, and this linen mini from Forever 21 is my go-to for casual summer nights. The flattering silhouette and button details make it feel a little special, but it’s simple enough to wear again and again (see similar styles at Free People and Urban Outfitters).

I paired it with some brown suede lace-up heels to dress it up a little and add some color. The nice thing about a LBD is that you can wear it with almost anything and it’ll look fine.

Wear it with a jean jacket and flats during the day, and throw on some earrings and heels for night. 

Sporty Spice

I’m not going to lie: I decided I needed biker shorts after I saw pics of Bella Hadid going to the club in a fun metallic pair by Yeezy. Sadly, I’m not a Hadid, so I went for a more understated black pair of shorts from Bandier.

Still, the shorts feel like a statement themselves, so I kept things simple with a black crop top (F21) and mini backpack (impulse purchase at Target). Honestly, I’m still figuring out how the heck to style these shorties. I think I could do better, but this outfit feels like a good entrée into the world of spandex evening wear.

Shoes are my trusty Nike Air Huaraches. I wish they were dad sneakers (the Hadids have also sold me on this), but I haven’t found the right pair yet. 

Ready to jump on the bike short bandwagon? These are sold out, but here’s another pair from Bandier.

Texas Tuxedo

I love a denim-on-denim look. When it comes to denim, I usually prefer vintage over new. This corset is actually the top half of a denim jumpsuit I purchased from the thrift store and cut in half. (That’s typical of my Frankenstein closet.)

My friend gave me this vintage Gap wrap skirt and I wear it all the time (Asos has a similar one). The shoes are from Shu Deal, a bargain footwear store which deserves its own story. I snagged the Diorissimo saddle bag on eBay two weeks before Dior reintroduced the style on the Fall 2018 runway. 

Pink Power Dressing

This is my personal recipe for nighttime power dressing: suiting, lingerie, and lots of pink. As much as I love this vintage Chanel blazer, it can get a little ‘80s realtor if I’m not careful. I like to wear it with a matching Victoria’s Secret slip and nude pumps for a modern night-out look. I think Elle Woods would approve.

Get the look by pairing your favorite oversized blazer with a pretty slip, or simplify things with a sexy blazer dress.

The Instant Confidence Boost

Do you know those garments that just make you feel good as soon as you slip them on? This Reformation dress (the Gwenyth) exemplifies that feeling to me. I love the delicate green floral pattern and lightly puffed sleeves; the sexy-yet-demure cut.

I paired it with snakeskin Steve Madden sandals, which are so comfy and match-almost-everything neutral. The purse is vintage Gucci from The Real Real and also goes with pretty much everything.