21 Feb 2024 • • by Amy

How to Style a Button-Up Shirt like Jenna Lyons


It took our marketing manager Amy approximately five seconds to come up with the muse for our latest pattern, the Jenna Button Up Shirt and Dress. That's because when it comes to style icons that know how to rock this look, Jenna Lyons (the one-time creative director for J Crew) is without a doubt at the very top of the list. Known for her signature ability to style up to four layers in a look and somehow not look silly, Lyons is a timeless combination of chic and cool, tough and girly. She never looks overdressed or out of place and yet she always manages to put something together that is totally unique, fresh and unexpected. We couldn't think of a better teacher to show us all the outfits we could make with our new wardrobe of button-up shirts – let's get into it.

One Shirt, But a Great Shirt

An introductory lesson in this styling class: the single button-up shirt, myriad ways. Pair it with a ballgown skirt, satin pants, or just jeans. Button it all the way up or undone to the belly button (one of our favourite Jenna signatures - no bra + sliver of skin = effortlessly sexy). Add a tie, a bowtie, a pearl necklace, or all three! Sleeves can be rolled up and flapping, rolled tightly, or all the way cuffed. The secret is all about balance; not too fussy or too sloppy, you want to look casual, unbothered, and like you just threw this on. Easy, breezy and beautiful. COVERGIRL.

One Shirt Under a Jacket

The sophomore lesson in Jenna Styling University is the button-up shirt under a jacket. The jacket can be a blazer, bomber, vest or leather moto, but the real trick is balancing the pants. Her logic with most of these looks is the perfect blend of casual and formal. If the jacket and shirt are classic or tailored, the bottoms are casual Friday. If the jacket is more unexpected, keep the other layers simple. Again, it's about contrast and most importantly feeling like yourself.

Sweater Over Shirt

Another layering option that shares the same principles as the jacket (a balance of the high/low mix). I love this red carpet look pairing a sequined skirt and statement jewels with what is essentially a novelty sweatshirt. The anchor in all these looks is the simple white collared shirt. Humble, yet totally holding the look together. Flawless!

Short Sleeve Over Long Sleeve

This one is more of an advanced look. Let's call it the AP class of Styling 101. Not for the faint of heart, this takes a little more work but is really all about the proportions. The short sleeve layer on top needs to be roomy enough so you don't look stuffed into your clothes and the neatly buttoned collar makes sure things don't get too messy visually. You can tuck your shirt tails in or leave them out for a break between the top and pants.

Sparkle Over Simple

I put this one in its own category because it deserves special consideration. Probably the hardest look to achieve, the trick here is the play of the materials. The shirt needs to be masculine (think banker) and the sparkle needs to be light as a feather. The style is in the contrast and the effect is so fun.

Don't Try This At Home

Listen, we can't all be Jenna Lyons and I think these last looks really prove why. Not just anyone can pull off tulle, army surplus and animal print fur in the same look, let alone double button-ups. There is a reason she is a masterful stylist and gets paid the big bucks. We bow down. But also DM us if you pull one of these off.

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