30 Ways to Upgrade Your Style This Fall

30 Ways to Upgrade Your Style This Fall

A wardrobe challenge for you to try

By Megan Collins | Last Updated: Nov 1 2017 | 2 min read

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

style upgrade, style update

Day 2: Dress up a plaid shirt

Day 3: Bust out your favorite leather jacket

Day 4: Opt for grey jeans over blue

Day 5: Relax in “fancy” sweats

Day 6: Wear a bold print

Day 7: Make monochrome pop in a bright color

Day 8: Dress up a shacket

Day 9: Dust off your favorite vintage tee

Day 10: Layer a denim jacket under a sport coat

Day 11: Top your hoodie with a topcoat

Day 12: Mix two textures

Day 13: Wear the most expensive thing in your closet

Day 14: Trade your sport coat for a leather jacket

Day 15: Wear your burliest boots with a suit

Day 16: Wear head-to-toe winter white

Day 17: Dress down a suit for Casual Friday

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

Day 19: Sport your favorite bright sneakers

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

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

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

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

Day 24: Sport your best athleisure for Black Friday

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

Day 26: Break out a Fair Isle sweater

update style

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

Day 28: Elevate your parka

Day 29: Try wearing denim head-to-toe

update style

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



I started Style Girlfriend to help guys look, feel, and act their best.