Which socks and when?

Your Stylist breaks it down

Has a newspaper article ever rattled a generation of women like that NYT piece on millennials and their no-show socks? Doubtful. What started as TikTok teasing in 2020 exploded into a full-on generational clash. Suddenly, millennial women - already spending a fortune to look younger - were spiraling: “Wait… are my socks aging me?”

We weren’t ready for this. I’m here to help. Let’s get into it.

A guide for today’s letter. Screenshot for later!

Shorts:

Let’s start with an easy one; sport shorts - the answer is YES! A cute sock is a great addition:

Athleta windbreaker $159 / Daily Drills shorts $96 / New Balance 408 $84 (size down half size)

Alex Mill jacket $225 / Buck Mason shorts $88 / Reeboks $89

Denim Shorts:

The plot thickens. It’s a yes for hemmed denim, but generally a no for cutoff denim, which is too beachy for a sock and shoe:

What a difference a sock makes! If you’re wearing cutoffs, stick with something summery like boat shoes Frame shorts $198 / The Great sweatshirt $175, Sperry boat shoes $99

It’s a yes for hemmed shorts:

pics via Pinterest

Dresses:

Styling dresses (or skirts) with socks depends on the length of the dress - too long, and you’re instantly too covered up. Hard NO:

Bagel wondering who would make this choice?!

A maxi dress requires a sandal or if you’re doing a sneaker, no sock. Xirena dress $225 love this and it has pockets - wearing small / J Haller sandals $525

Maxi dress + sneakers done right via Kendall Jenner

Midi length skirts show enough skin that socks make it cute and not heavy Suzi Kondi skirt $375 size small / Soldout NYC tank $85 / Reebok sneakers $85 / Amazon socks $11

A closer look at the socks - the rolled top means they and won’t squeeze your ankles or leave a sock mark

Socks + Cropped Jeans:

Peekaboo! I see your socks. A thoughtful way to elevate your look is matching your sock to your shoe - black socks/black sneakers is an easy place to start:

Ozma sweater $218 / Joes jeans $99 size up I’m wearing 28 / Adidas Spezial $110 (jacket is old from Source Unknown)

Plot twist: It’s mid July, 90 degrees in the shade. You need to wear jeans because sometimes you just have to. But socks?! Absolutely not. You’re so grateful for the wind on your ankles you’ll take a breeze wherever you can get it.

Ozma tank $138 / Joes jeans $220 / Adidas SL72 $100

And just like that, we’re back where we started: a millennial woman and her no-show socks. But hopefully now you’ve got the intel to choose your socks (or not) with confidence. You’ve got this.

xo

Abby