Outfit Inspiration

30 Ways to Upgrade Your Style this Fall

Upgrade your look for cooler weather

Fall officially begins tomorrow, and as the temperature continues to drop, it can be hard to know what to wear. Loads of light layers? A wool sweater with swim trunks? Trust us, we get it.

We’ve been stocking your closet with fall sweaters and jackets, and now it’s time to inspire you with some full-on cool weather lewksWe can all use outfit inspiration from time to time, whether that’s ideas on how to incorporate new pieces to our wardrobe rotation or new takes on wearing the items buried in the back of the closet. So below you’ll find a men’s fall style challenge for 2018, with outfit ideas for the next thirty days.

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

via Esquire UK

Day 2: Break out your favorite bomber

via Scout Sixteen

Day 3: Opt for black jeans over blue

via Sneaker VI

Day 4: Get your fleece on

via Daily Mail

Day 5: Wear a bold pattern

Day 6: Sport a plaid shirt

via One Dapper Street

Day 7: Make “sleaze style” work for you

Day 8: Keep things simple with a t-shirt and jeans

via Chubstr

Day 9: Go monochrome

via Esquire

Day 10: Mix dress pants and a leather jacket

via Isaac Likes

Day 11: Camouflage a casual look with a topcoat

via Getty

Day 12: Try (just try) a hip pack

via Oh Anthonio

Day 13: Wear the most expensive thing in your closet

via Getty Images

Day 14: Add a stripe

via Levitate Style

Day 15: Flash some ankle in cropped pants

via Teen Vogue

Day 16: Two words…White. Jeans.

via TrendStyled

Day 17: Just wear a suit

via Getty

Day 18: Wear a color you’ve never worn before

via Bright Bazaar

Day 19: Sport your all-time favorite sneakers

via Nice Kicks

Day 20: Free day! Wear a double-breasted suit *OR* some tie-dye. Your call.

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

via @thebigfashionguy Instagram

Day 22: Sport a sport coat

via Harper’s Bazaar

Day 23: Try a pair of joggers (if you haven’t already)

via The Idle Man

Day 24: Wear a fabric you’ve never worn before

via The Gentleman Blogger

Day 25: Pull on a turtleneck

via Menswear Dog

Day 26: Wear something summery (for the last time this year)

via Men’s Style Pro

Day 27: Invest in a “statement” coat

via The Idle Man

Day 28: Go head-to-toe in denim

via Notoriously Dapper

Day 29: Wear something *super* outside your comfort zone

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


Still feeling overwhelmed? SG can help

If you’re ready to upgrade your style but dread the thought of shopping for new clothes…consider having Team SG shop for you! We’re obviously biased, but clients tell us the personalized online shopping lists we make for them are total game changers!

Let us rescue you from shopping fatigue and sartorial apathy. We can promise the kind of personal attention and care that will make you feel like the best version of the awesome guy you already are! Ready to seriously improve your closet and your confidence? Give us a shout.

> Get more style and dating tips from SG HQ