Outfit Inspiration

30 Ways to Upgrade Your Style This Fall

A wardrobe challenge for you to try

By Megan Collins | Last Updated: Nov 1 2017

This fall, we’ve been stocking your closet with layers and sharing tips and tricks to transition your wardrobe for a temperature drop. Now in November, we want to help take your cool weather wardrobe to the next level, with a style update.

Below, we cherry picked four weeks’ worth of looks for the next 30 days. It’s easy in November to fall back on function over fashion; trust us, we get it. We can all use inspiration, whether to add new pieces to our wardrobe rotation or with ideas on how to wear items already in your closet in new ways.

Think of this fun challenge like an operating system upgrade for your fall style.

The best part? You can wear denim every damn day (if you really want to). Take that No Jeans January! And of course, we want to see what you come up with, so be sure to share photos with the hashtag #SGfall30.

Day 1: Wear something orange

photo: GQ

Day 2: Dress up a plaid shirt

photo: The Cut

Day 3: Bust out your favorite leather jacket

Day 4: Opt for grey jeans over blue

photo: E! Online

Day 5: Relax in “fancy” sweats

photo: Just Jared

Day 6: Wear a bold print

photo: Tom and Lorenzo

Day 7: Make monochrome pop in a bright color

photo: Upscale Hype

Day 8: Dress up a shacket

photo: Just Jared

Day 9: Dust off your favorite vintage tee

photo: Levitate Style

Day 10: Layer a denim jacket under a sport coat

photo: Lookastic

Day 11: Top your hoodie with a topcoat

photo: Pinterest

Day 12: Mix two textures

photo: LookLive

Day 13: Wear the most expensive thing in your closet

photo: Instagram c/o Sami Slimani

Day 14: Trade your sport coat for a leather jacket

photo: GQ

Day 15: Wear your burliest boots with a suit

photo: To The Kanye

Day 16: Wear head-to-toe winter white

photo: Oh Anthonio

Day 17: Dress down a suit for Casual Friday

photo: GQ

Day 18: Keep it simple with a white t-shirt and jeans

photo: Daily Mail

Day 19: Sport your favorite bright sneakers

Day 20: Update your basic dress shoes with something..a little more interesting

photo: Instagram c/o Floyd Mayweather

Day 21: Wear something you haven’t worn in at least six months

photo: Vogue

Day 22: Travel to Thanksgiving in style in a sport coat and jeans

photo: D'Marge

Day 23: Wear an elastic waistband (it’s Thanksgiving!)

photo: The Sun

Day 24: Sport your best athleisure for Black Friday

photo: Oh Anthonio

Day 25: Wear a color you haven’t worn in awhile

photo: Celebuzz

Day 26: Break out a Fair Isle sweater

photo: Billboard

Day 27: Wear something summery (for the last time this year)

photo: Instagram c/o Marlon Teixeira

Day 28: Elevate your parka

photo: HollyNolly

Day 29: Try wearing denim head-to-toe

photo: GQ

Day 30: Re-wear your favorite look from the month..you made it!

photo: FashionBeans