The 13 Best Back-to-School Trends According to Top Chicago Bloggers

The 13 Best Back-to-School Trends According to Top Chicago Bloggers

Chicago fashion bloggers Dana Weiss of “Possessionista” and Jena Gambaccini of “Chi City Fashion” offer their tips for sending kids to the top of the fashion class with those 13 back-to-school trends (and three don’ts!)

1. Comfort is King

“I think fall 2016 back-to-school is really about comfort and casual,” says Weiss. “It’s just about being cool and not looking like you tried too hard.”

Marcus Striped Pullover Sweater by BB Dakota, $89, Juniper Boutique
Marcus Striped Pullover Sweater by BB Dakota, $89, Juniper Boutique

2. Vest in Show

“Everyone says it’s all about layering, and it is, but fall 2016 will be great because there are so many more options now to layer, like with really cool vests,” says Gambaccini.

Tucker + Tate Reversible Faux Shearling Vest, $48, Nordstrom
Tucker + Tate Reversible Faux Shearling Vest, $48, Nordstrom

3. Supersize

Oversized cardigans are always a fall staple because they’re easy to throw on over an outfit and instantly create chic layers, and this fall is no exception.

Splendid Girls’ Wrap Cardigan, $38, Bloomingdale’s
Splendid Girls’ Wrap Cardigan, $38, Bloomingdale’s

4. Turn Up the Volume

“It’s fun to experiment with layering by adding volume and texture, and it’s my suggestion for transitioning from summer to fall,” says Gambaccini.

Stella McCartney Appliquéd Tulle Dress, $152, Barneys New York
Stella McCartney Appliquéd Tulle Dress, $152, Barneys New York

5. Flannels Forever

“There’s a lot of [fashion] influence from Seattle and Canada right now, so shockingly, we’re seeing flannels tied around the waist again,” says Weiss.”

Kendall & Kylie Button-Down Plaid Flannel Shirt, $37, PacSun
Kendall & Kylie Button-Down Plaid Flannel Shirt, $37, PacSun

6. Dare to Flare

Step away from the skinnies! Flared and wide-legged pants are a fun jean alternative, and this trend is back in full swing for the fall.

Treasure & Bond High Rise Skinny Flare Jeans, $99, Nordstrom
Treasure & Bond High Rise Skinny Flare Jeans, $99, Nordstrom

7. Velvet

“I wouldn’t say you should wear a full velvet back-to-school outfit at the end of August, and it can read a little more holiday,” says Gambaccini. “But people are doing a good job of finding a way to make it not so holiday and incorporate it into everyday life.”

Silence + Noise Tavi Crushed Velvet Cropped Tee, $34, Urban Outfitters
Silence + Noise Tavi Crushed Velvet Cropped Tee, $34, Urban Outfitters

8. ’90s Vibes

“You’ll see a lot of ’90s inspiration,” says Weiss. “A lot of laid-back flannels and plaids.”

BDG Shannen Plaid Button-Down Shirt, $69, Urban Outfitters
BDG Shannen Plaid Button-Down Shirt, $69, Urban Outfitters

9. All the Right Puff

“A few designers this season revamped the puffer coat, which is kind of neat, especially in Chicago where everyone has that basic puffer coat and it’s 100 percent for practicality and not style,” says Gambaccini. “I think something like that will trickle down to back-to-school.”

Isabel Marant Etoile Reversible Celia Puffer Jacket, $730, Barneys New York
Isabel Marant Etoile Reversible Celia Puffer Jacket, $730, Barneys New York

10. Sporty-Chic

Luxury sneakers and athleisure sportswear are summer trends that aren’t fading anytime soon.

Ella Tank, $63, Londo Mondo
Ella Tank, $63, Londo Mondo

11. Add on Inches

“For back-to-school you can’t show your stomach, so we’re going to see two-piece outfits of crop tops and shorts in the summer transition into a flowy pant and slightly longer shirt,” says Weiss.

Ralph Lauren Girl's Two-Piece Striped Top & Skirt Set, $38, Saks Fifth Avenue
Ralph Lauren Girl’s Two-Piece Striped Top & Skirt Set, $38, Saks Fifth Avenue

12. Layer Up

“The best thing to do is always layer,” says Weiss. “If you take a tank top and jean shorts you wear in the summer months, and then throw on a longer flannel, you’ll extend it into those warm weather fall days.”

Wool Blend Pea Coat, $495, Burberry
Wool Blend Pea Coat, $495, Burberry

13. Jump for Joy

“Schoolgirl jumpers were on the runways for fall 2016, sort of that sleeveless dress that you wear with a turtleneck or t-shirt underneath to go into fall/winter, and it works well for back-to-school,” says Gambaccini. 

Topshop Patch Pocket Denim Pinafore Dress, $68, Nordstrom
Topshop Patch Pocket Denim Pinafore Dress, $68, Nordstrom

Bonus: Trends that don’t make the grade

Crop Tops

“From a practical standpoint, we live in Chicago. I think that crop tops are going to fade into the back,” says Weiss. “For the colder weather, between not being school appropriate and weather appropriate, we’re not going to see crop tops.”

Lace-up tops

“Lace-up tops have been super popular, but I’m not sure in a year from now if people will still be wearing them,” says Gambaccini. “I think they’ve been really overdone. If I’m sick of them, I’m sure other people are too.”

Skinny Jeans

“I definitely think we’re seeing a move away from skinny jeans and toward these wider legged pants and flares,” says Weiss.


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