Why I Keep Wearing the Same Thing Over and Over Again (and Why That’s Liberating)

I've found that the secret to finding your personal style isn’t more clothes—it’s better ones you never want to take off.

Molly Howard outfit selfies
(Image credit: Molly Howard)

Modern-day fashion—and the way we’re constantly bombarded by it—has become an overwhelming, sometimes exhausting part of our lives. Whether you work in the industry or not, we’re flooded with influence, pressure, and passing trends every single day, through every medium we touch. The avalanche of product can make even the simple act of getting dressed feel paralyzing.

Of course, I know I’m guilty of feeding it: I run a womenswear brand, La Ligne, which makes up most of my wardrobe (as you'll see below). But lately, I’ve realized this onslaught has forced me to get clear about my own approach to style—who I want to be when I get dressed, what really matters, and how I can get there. Here's what I've learned.

If It’s Not Comfortable, It’s Not Happening

For me, comfort breeds confidence. I used to work in finance, and, after a twenty-hour workday, I could barely make it off the elevator before my “business casual” attire littered the apartment of my hallway. (I wanted it off my body.) I have no interest in wearing clothes that I’m acutely aware of all day—falling out of place every time I move, rough to the touch, leaving an imprint on my skin by the time I take it off.

But craving comfort doesn’t mean I want to be in sweats all day. (No shade if you do—try the Colby.) I believe we can be physically comfortable while also, more emotionally, feeling comfortable in the confidence that comes from looking good. And good doesn’t need to mean a full face of makeup or a heel: To me, it should just be thoughtful. Considered. Having a point of view and owning who you are.

That’s why we started La Ligne, to make clothes that fit and flatter, that a woman can weave seamlessly into her life and just feel a little bit better for it. Season after season. Still relevant. Still urgent. Still comfortable.

Find Pieces Worth Keeping

Molly Howard outfits

(Image credit: Molly Howard)

The true test of clothing’s value is its staying power. I don’t invest in anything I know I’ll want to get rid of in a year. Which is why my wardrobe is a well-curated mix of La Ligne, vintage and, sorry, The Row. We don’t need more clothes. We need better ones. The kind you keep, re-wear, re-style, and actually live in.

That said, I make one exception: tees—specifically, vintage and graphic ones, which I buy constantly. At least half my life is spent in Colby Pants and a tee. My favorite tees come from Mothfood, Strike Anywhere (which I buy oversized), Wyco Vintage, Intramural, Front General Store (more for sweatshirts, which I wear in place of a tee when it’s colder), eBay if you have the patience, and Etsy more recently for baby tees. If I’m not in a graphic tee I’m in a solid white tee—hence the names of *our absolutely perfect* Molly Tee and Mol Tee.

Easy, Little Change-Ups Open Up So Many Outfit Possibilities

Molly Howard outfits

(Image credit: Molly Howard)

My go-to outfit can be subtly remixed by swapping the Colby for a straight-fit skirt, like our Lyon or Bianca, especially with our Dianna Agron trench layered on top. All versions of this look are easily paired with City Flip Flops, these Jil Sander flats, or these Dries sneakers in white. (Even though they’re a little too popular for my liking, they’re flat in the front in a way that makes them look good with everything).

A Good Pair of Jeans Goes a Long Way

Molly Howard outfits

(Image credit: Molly Howard)

I do think good denim is probably the most important closet staple. I rotate between vintage finds, our Marilyn, and the Mol. The latter is wildly versatile—it can be dressed up or down, high or low. I always feel safe in jeans, an oversized white button-down (only buttoned in the middle, please), a chic heel, and a good pendant necklace. I have succumbed to (and still crave many) pieces from Lisa Eisner, Dezso by Sara Beltran, Sophie Buhai, Ten Thousand Things, and, speaking of classics, most anything Elsa Peretti.

When the Occasion Calls

Molly Howard outfits

(Image credit: Molly Howard)

When it feels right, I enjoy getting dressed up. I recently wore our new Cora Skirt and styled it exactly as we did on our website, with a Ben Cardigan slightly unbuttoned at the bottom. I felt really put-together but still luxuriated in the comfort of the fabrics. The skirt is 100% cotton, breathable, and soft, and the sweater, like all of our Ben styles (named after my husband), is probably the most comfortable thing I own.

Which brings me to the Ben Polo, another forever style I keep in constant rotation. That and the Lean Lines Cardigan (extremely cute with only the top button done, over a graphic tee) basically live on top of my dresser—I never bother putting them away because I wear them constantly.

I styled this outfit with flats, but it would have been just as cute with these heels (if I owned them). And when the occasion is truly fancy, my first stop is always Desert Vintage. Or Alaïa.

Pulling It Together

Molly Howard outfits

(Image credit: Molly Howard)

The finishing touches to any of these outfits are some well-curated accessories—a little flair, if you will. I own Charvet belts in every color of the rainbow. (If you’re in Paris, go there before you see the Mona Lisa. The perfect belts… and shirt, slippers, boxers, cufflinks, and on and on. My happy place.) They’re also my top men’s gift recommendation.

When it comes to bags, I go very classic or slightly kooky—and I mostly go to The Row. My most-used work bag is the Park Tote. For the weekend, when I’m chasing my child around the city, it’s the Banana Bag. The 90s Bag, which barely fits my phone, is for nighttime. All of these are both refined and luxurious, and I feel elevated when I use them. But I get more joy from my vintage Fendi Baguettes and anything leopard print.

I could do this all day, but I’ll close with these—my true bliss, soon to be yours, too.

Molly Howard
CEO and Co-founder of La Ligne

Molly Howard is the co-founder and CEO of La Ligne, the New York–based womenswear brand known for its modern interpretation of the timeless stripe.