HELP, DELIVERED:

What Should I Wear This Season?

By: Caitlin Madden

Is it winter? Is it spring?

I always say that spring is my least favorite season. Which, when I think of it, seems crazy. The flowers are blooming, it’s getting warmer, staying light outside later, and you can finally emerge from winter hibernation. What I have realized is, when I say I loathe spring, my disdain comes from never knowing what to wear.

Throughout my life, one of my biggest pet peeves has been not dressing appropriately for the weather. It used to drive me up a wall when my little brother would wear basketball shorts in the middle of January in suburban New Jersey, or when my Californian college classmates would wear faux fur coats on a 62° day in NYC.

So, when springtime comes around and I find myself in a sweater and boots on a warm afternoon, it is my fashion nightmare. It’s that weird in between warm and cold weather where you can put on a jacket and go to work, but by lunchtime you’re sweating. My wardrobe seems to be the wrong mix of fabrics, colors and overall vibes for this type of weather.

If I’m going to have any chance of rehabilitating my relationship with spring, I think I have to start with my outfits.

I need pieces that transition from one season to the next – sometimes all in the same day.

Luckily, I work at Free People.

Sabine Articulated Shirt

TRANSEASONAL TOPS

There is no wardrobe staple more versatile than the button-down shirt. Wear it layered under a jacket or a sweater on colder days, or on its own when it warms up. Our new favorite style, the Sabine Tailored Shirt, has a slouchy silhouette that feels totally on-trend for spring and can be worn under or over so many things.

ADD (OR SUBTRACT) A JACKET

When it comes to transitional jackets, we love choosing fabrics that provide some warmth but still feel light and airy. While denim jackets are a spring staple, we also gravitate toward suede and quilted styles that wouldn’t look too out of place on a winter’s day. Liner coats with a little bit of puffiness or oversized shirt jackets make perfect picks.

We The Free Zazu Reversible Liner

Nocturnal Patterned Cardi

SPRING-ISH SWEATERS

This type of weather is where the cardigan really gets her flowers (sometimes literally). Choose a lightweight fabric and it can double as a shirt, or you can layer something underneath then tie it around your shoulders if it gets warm. For pre-spring, going with a lighter color or a fun floral print helps a sweater feel a little less tied to winter.

DO-IT-ALL DRESSES

My dresses sit in my closet all winter long just waiting for it to be their turn again, and while this time of year feels a little too soon for baring leg– an easy midi is the perfect compromise. This one from our free-est collection is lightweight and layerable in a body-skimming, t-shirt inspired silhouette that essentially turns your dress into a wardrobe basic.

Good Feels Slim Midi

We The Free Jam Session Relaxed Capri Jeans

AWKWARD LENGTHS, ALWAYS

Not ready for full-on shorts yet, but ready to switch up your jeans? Awkward-length bottoms are our favorite transitional trend. These just-below-the-knee styles are cooler than the average capris with a wide silhouette that pairs well with tall boots when it’s cooler or sandals and sneakers when it warms up.

UNDERNEATH EVERYTHING

We can’t talk about transitional dressing without mentioning the layers we lean on for every outfit. Our Intimately FP collection is always our first stop when putting an outfit together, and when we’re talking about outfits that might have a little midday transformation, the foundation is extra important. Start your look with a lightweight long-sleeve that looks great layered up or all alone.

Big Love Rib Long Sleeve

Toggle Poncho

PONCHO AND GO

Hear me out: a knit poncho might be the perfect winter-to-spring topper. It’s cozy yet flowy, covered but not too much, and super easy to slip on and off. It’s an over-everything layer that strikes the perfect balance needed for those not-hot-but-not-cold days. Long live the poncho!

HEAD-TO-TOE TRANSITIONAL

One of my biggest issues with spring dressing is shoes. I’m over my boots, but not ready for exposed toes, and don’t want to only wear sneakers. This is where clogs and mules come in. They’re more spring-forward than a sandal, but just as effortless and they go with pretty much everything. Not into a clog? You can always add socks to your favorite footbed sandals!