Jessie Loves: Styling Tips From My Childhood Self

And everything I'm adding to my fall wardrobe.

I feel like a lot of my life has been a journey back to being the person I was in kindergarten. There are so many similarities between who I am now and who I was in Ms. Looney’s class at Flagg Street School in Worcester, MA — a little bit shy, artistic, only wanting to hang out with my girlfriends (no boys!). And my style, too. For as long as I can remember, nothing has made me more excited than picking out an outfit that feels like a true expression of me.

I did not grow up in a family that particularly valued fashion. I had to be very creative to put together things that I loved. I did have a stylish Grandmother, Bama, with little size 5 feet and a closet of ball gowns she let me clomp around in whenever I wanted. But back home on Berwick Street, I wore mostly hand-me-downs from my brother.

My grandmother Bama

I think it must be the humiliation of having to wear my blue Snoopy bathing suit to ballet class or my brother’s “Maurice the Pants Man” corduroys to softball practice that turned me into a fashion designer. Or the fact I wasn’t allowed to have Barbies. Or that I became a Girl Scout wearing those same damn cords while everyone else had on the official Brownie uniform.

When I look back at old photos, I see the same me staring back. And I see so much of the stylistic through line of my aesthetic even then. Here are six fall styling tricks from my childhood self, and everything else I’m adding to my seasonal wardrobe.

1. Ballet Flats

Here I am as a “Little Doll In A Toy Shop” for my recital at Charlotte Klein’s dance studio. I was bored in my tap/ballet class, I faked being sick a lot of the time. It was endless shuffle ball changes and pliés. My sole purpose for being there was getting a brand-new pair of ballet flats each semester (and a little bouquet of flowers after the recital). For our performance they spray-painted the soft pink leather with metallic silver paint. This meant a new pair every time a class session started. Worth the pliés.

Ballet flats continue to have a huge moment. I personally think ours are the best. They are so soft — I wanted them to feel exactly like my little ballet shoes, only with a leather outsole so you can wear them around everywhere.

If you look closely, this photo’s a lesson in staying true to yourself, too. Zoom in and you’ll see my bulky underwear drooping down inside my tights. Each recital it was pleading and begging from the adults that I not wear underwear with my costume and tears from me because I just could NOT do it. It felt so weird, gross and uncomfortable. I’m still the exact same way and can’t stand to not be covered up.

I’m wearing our Liz Fleece, Molly Jean, and Leonie Flat

2. The Mix

This is one of my favorite photos. It’s a bit blurry because it’s from a group photo of me and all my aunts and uncles and cousins on my grandparents’ front porch. I see the same face and the same style. I’m wearing a hand-me-down sweatshirt from my brother who had just been to sleep away camp — Camp Takota. And a turtleneck (and I’m sure corduroys). But I’ve got a pretty, frilly clip in my hair.

I still love that tomboy/frilly mix. And even though LR can be quite “feminine” and sometimes dressy, my style is most often casual. I love to wear something girly with a rugged workwear pant. That juxtaposition is just so cool to me. It’s not too fancy, not too casual. Here’s a mix I’m loving lately: Our new denim workwear jean, paired with our pretty new tie-front vest and statement bow shoes.

Our Lolo Long-Sleeve, Callista Top, Molly Jean, and Noa Flat

3. Intarsia Knits

I’m very lucky that I have a mom and had a grandmother who were incredible knitters. This sweater was knit for me by my mom. The color palette is so beautiful — cream and navy and maroon. I love it. it was hard to teach me to knit because I’m left-handed but I worked and worked at it sitting on the couch with my grandmother watching “Days Of Our Lives” (she had a crush on Patch) and eventually picked it up.

Our Idris Sweater, Caroline Skirt, and Rachel Loafer

Over the years I became adept at intarsia knitting (where you switch colored yarns in and out of the knitting to create a pattern) and I always appreciate the skill and technique involved when I see an intarsia knit. This fall we have a leopard intarsia cardigan and sweaters and vests with floral motifs knitted in. I love how special they are. Here’s a photo of my mom knitting in the middle of a cocktail party — something I do often.

4. Jellies

I wore a lot of jellies growing up because I thought they were so cool and also because they were quite affordable. Vast stretches of my childhood were spent on my front walkway jumping rope in my jellies. This photo was taken the first time I ever traveled overseas — to Paris and London — in the 4th grade. I was supposed to leave my doll, Kana, at home with my grandmother but I just couldn’t do it. (Late bloomer then, late bloomer still). Back in the day my mother felt it was important to dress up when you went on a plane. I remember that dress so clearly. It was from T. J. Maxx and had a great texture to the fabric and little shoulder pads. It was so ‘80s — including my bangs! I love the jellies most of all and especially the way I wore them with little socks. I want to try wearing our jellies with socks this fall. They sold out so fast, but they’re available for preorder on our site!

Matching in our Rhys Jellies

5. Pops Of Red

I keep putting red into the collection. I can’t stop. Red is my favorite color at the moment. Red from my geraniums, red from our Landon flat and Laney dress. It is a color that pops and makes me so happy and it’s a color that is having a major moment right now.

Our Laney Dress and Landon Flat

6. Layering Sweaters Underneath!

My grandfather always had a Polaroid camera when I was growing up. We loved waving the film around waiting for the picture to emerge. This one is so old it has cracks now. Look at my little frilly sweater underneath a pair of OshKosh overalls.

When we had a party in January, our friend Sjournee was wearing a hooded sweatshirt underneath our fancy big bow dress. I loved that mix. I continue to see a trend of people wearing sweaters in interesting ways — tied crossways on the torso, layered together and worn underneath a dress. I styled my favorite Hey Gang hoodie under our new Lilly dress, and can’t wait to wear it this way all season.

Our Lilly Dress and Heidi Boot

Other Things I’m Loving For Fall:

• I really want to get this oversized Underwater Weaving tote from my friend Erin. It’s so chic and useful.

• This mint camp shirt from Mr. Larkin. I love the brown / mint color combo.

• Our little bustier vest. I love the fabric and the layering possibilities are endless.

• Someone on Reddit (I’m obsessed with Reddit) recommended “vintage Givenchy jewelry” as a search term on Etsy. Some very cool stuff!

• My boot dreams came true with our Heidi. It’s that perfect mix of ‘70s and modern and the color is so versatile. I’m obsessed. I’m going to wear these all year long.

• Loafers with socks. I am excited to try this look. The sock I think should be slightly athletic and chunky. Maybe these socks.

• This triblend hoodie is going to be a staple for me. I’ve worn it with our Lilly dress, and I think it could be cute with a fancy skirt.

…And one thing I hate*:

I’m personally not a fan of an oversized sexy blazer.

*my husband’s suggestion to always include one thing I don’t like at the end. Ha!