(Outfits Of The Month)

Get Ready For Fall By Trying Out These Cute Looks

Kick-off the season in style.

Anne Laure Mais on Instagram

September is high up on a fashion aficionado’s list of favorite times of the year for seeking sartorial inspiration. For those who reside in New York, London, Milan, or Paris, simply stroll around your city during fashion week to see the impeccable street style ensembles IRL. If you’re located elsewhere, not to worry: the cool temperatures allow for genius layering techniques — so take notes of the creative ideas you come across as you’re out on the town. And of course, don’t forget to join in on the fun, too — get ready for the upcoming season by assembling cute fall outfits over the next 30 days.

This month is all about stocking your wardrobe with the biggest fall 2021 trends. According to shows like Etro and Versace, expect to see plenty of printed party pants out and about (not to worry, they won’t be hard to miss). Plus, contemporary brands like Hosbjerg and Gimaguas are co-signing the trend, too. As for the top half of your outfit, you’ll be happy to hear that the sweater vest craze is only gaining momentum through fall, thanks to fashion girl-favorite labels like Ganni and Rejina Pyo. And now that boot season is upon us, it’s time to think about what styles you want to add to your repertoire. This season, you can’t go wrong with a runway-approved metallic finish or a slouchy silhouette.

Now that you have the 411 on all the need-to-know trends, test drive them with the 30 cute fall looks below — which happen to be perfect for all the excursions you have on the docket this September.

We only include products that have been independently selected by TZR’s editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

Summer Feels

Not ready to let go of the carefree dog days of summer quite yet? Remind yourself of the good times you had over the past few months with this printed top featuring summer photos from Lirika Matoshi.

Transitional Footwear

No need to stash away your sandals under your bed this month. On those warm days, pair them with a button-down and denim and you’re good to go.

Time For A Topper

The key to keeping your summery pieces around for a bit longer is throwing a topper into the mix. For this, a trench coat is a versatile option to have hanging in your closet.

Cabin Weekend Uniform

Have a weekend at the cabin penciled into your fall schedule? You won’t want to forget your plaid flannel shirt. From roasting marshmallows to exploring the local town, you’ll be ready for wherever the trip takes you.

Make Old Feel New

Breathe new life into a vintage blazer but throw a belt over it. Consider skipping pants and sporting the outerwear as a dress. Then, finish off with knee-high boots and your outfit is complete.

Saturday Hike

Yes, you can still wear your athletic bike shorts this month. Team them with an exciting crewneck sweatshirt and you’re all set for a low-key hike or afternoon adventure to the farmer’s market.

Spruced Up Sweats

Since loungewear is the norm these days, try sprucing up your sweats with a luxe cardigan and graphic tee. The outfit will transition your WFH day to evening errands in a pinch.

Sporty Touch

A baseball cap can instantly make a black suit feel less stuffy. Even better: The accessory is ideal for bad hair days or when you’re out of dry shampoo.

A Match Made In Heaven

If you’re active on social media, you already know about the fashion world’s obsession with matching sets. Gett on board with the effortless trend by scooping up a vivid option that can be worn year-round.

Laid-Back Athleisure

Have a tennis match at 5:00 pm and dinner at 6:30 pm? Not a problem. Add on sleek loafers or Mary Janes to a tennis skirt and hoodie outfit for a sporty-chic ensemble.

Punch Of Color

All a white blouse and jeans duo needs is a splash of color via an accessory. A bright pink handbag will do the trick.


Here’s a styling trick you might not have tried yet: Wearing a long oversized top as a dress. Just make sure to wear spandex underneath in case it’s windy out.

Loud Statement

Now that it’s jacket season, make a statement with yours by opting for a cool patchwork style. Style the eye-catching piece with simple khakis and sneakers to allow it to have its shining moment.

Add Some Glitter

You don’t need to wait for the holidays or New Year’s Eve to wear glitter. In fact, a sparkly pair of boots add just the right amount of pizzaz to a neutral ensemble.

Impactful Details

Don’t underestimate the impact an oversized collar can have on an outfit. Layer it under a pared-back jacket and all eyes will be on the cool detail.

Funky Flare

Flared jeans are having a huge moment, so consider adding the funky silhouette to your denim lineup. Style the bottoms with everything from chunky loafers to simple white sneakers.

Western Vibes

Welcome to the season of fringe. Embrace the quirky trend by investing in a fringe jacket this fall. Pair the western outerwear with an animal print trouser for a surprisingly chic combination.

Clogging Around

Whether you love them or not, clogs aren’t going anywhere. If you’re not keen on the traditional wooden silhouette, give a leather or rubber iteration a go.

No-Fail Combo

A dress and sneakers outfit is a great duo to have at your disposal in case you’re simply at a loss on what to wear. Add on some dainty jewelry and you have an outfit ready for just about an activity,

Have Some Fun

Fashion shouldn’t be overly serious, so try having some fun with your fall ensembles by playing with mushroom and floral printed pieces. The more quirky symbols you add into the mix, the better.

Easy One-Piece

ICYMI: A bike-shorts bodysuit is a must-have piece this season, according to fashion girls. As it turns out, they are the perfect layering piece for a blazer or long jacket.

Grocery Run Chic

Grocery shopping while you’re half asleep? You can keep on your cozy boxer shorts for the occasion. To make them appropriate for outside the house, throw on a crewneck sweatshirt and chic clogs.

Party Pants

If you feel like you’re falling into a fashion rut, a pair (or two, or three) of printed pants are exactly what you need in your life. You’ll instantly brighten up every room you walk into.

Minimalism At Its Finest

An all-white ensemble is always a good idea, even after Labor Day. For those who love a smidge of color, slide on a bright heel or bootie.

Wedding Season

Chances are your weekends are filled with weddings this month. Arrive at the event in a chic striped number, like Christopher Esber’s iteration below. It certainly won’t be a one-time-only look.

Bring Out The Leather

The moment you’ve all been waiting for is here: leather season. Styling-wise, you can’t go wrong with pairing black leather trousers with a coordinating turtleneck.

Classic Combo

When in doubt, throw on your go-to white tank and jeans pairing. But instead of strappy sandals, pull out your favorite fall boots to make the outfit cold weather-approved.

Updated Accessories

Take cues from the Copenhagen Spring/Summer 2021 runways and swap your glitzy necklaces for a silk scarf. The easy styling technique really packs a punch to a simple cardigan and skirt getup, as displayed below.

Canadian Tuxedo 2021 Edition

Ah, an oldie but a goodie — the Canadian tuxedo. Give the signature style a 2021 spin by opting for slouchy separates.

Back To Dressing Up

Miss the feeling of throwing on a dress or skirt? Change that by bringing out a luxe midi skirt, even if you aren’t planning on leaving the house. The bottom makes for a comfortable alternative to your work trousers.