30 cute fall outfits to wear every day in September

September is high on a fashion enthusiast’s list of favorite times of the year for 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 IRL ensembles. If you’re located elsewhere, don’t worry: the cool temperatures allow for awesome layering techniques – so take note of any creative ideas you come across while in town. And of course, don’t forget to have fun too – get ready for the season ahead by putting together some cute fall outfits over the next 30 days.

This month, it’s all about stocking your wardrobe with the biggest trends for fall 2021. According to shows like Etro and Versace, expect to see a lot of printed party pants (don’t worry, they won’t be hard to miss). In addition, contemporary brands like Hosbjerg and Gimaguas are also co-signing the trend. When it comes to the top half of your outfit, you’ll be happy to hear that the cardigan sweater craze only picks up steam in the fall, thanks to girl-favorite brands like Ganni and Rejina Pyo. . And now that boot season is upon us, it’s time to think about which styles you want to add to your repertoire. This season, you can’t go wrong with a runway-approved metallic finish or a loose silhouette.

Now that you have the 411 on all the trends you need to know, test them out with the 30 cute fall looks below – which are perfect for any excursion you have on the schedule in September.

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Summer feels

Not yet ready to give up the carefree heatwave days of summer? Remember the good times you had in recent months with this printed top with summer photos by Lirika Matoshi.

Transitional shoes

No need to store your sandals under your bed this month. On hot days, team them with a button-down shirt and jeans and you’re good to go.

Time for a Topper

The key to keeping your summery pieces a little longer is to toss a garnish into the mix. For this, a trench coat is a versatile option to hang in your wardrobe.

Weekend cabin uniform

Do you have a pencil cottage weekend in 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 wherever your journey takes you.

Make old feel new

Breathe new life into a vintage blazer, but throw a belt on it. Consider skipping pants and wearing the outerwear like a dress. Then finish with tall boots and your outfit is done.

Saturday hike

Yes, you can still wear your sports bike shorts this month. Pair them with an exciting crewneck sweatshirt and you’re ready for a low-key hike or an afternoon farmer’s market adventure.

Revivified Sweatshirts

Since loungewear is the norm these days, try refreshing your sweatshirts with a luxe cardigan and graphic tee. The outfit will make the transition from your day from the WFH to the evening races in the blink of an eye.

Sporty touch

A baseball cap can instantly make a black suit less stuffy. Better yet: the accessory is ideal for days of bad hair styling or when you run out of dry shampoo.

A match made in heaven

If you are active on social media, you are already familiar with the fashion world’s obsession with matching sets. Get on board with the trend effortlessly by picking up a lively option that can be worn all year round.

Relaxed athleisure

A tennis match at 5:00 p.m. and a dinner at 6:30 p.m.? No problem. Add stylish loafers or Mary Janes to a tennis skirt and a hooded outfit for a sporty-chic ensemble.

Color punch

All a white blouse and jeans duo needs is a pop of color via an accessory. A hot pink handbag will do.


Here’s a style tip you might not have tried yet: wear an oversized long top as a dress. Just be sure to wear spandex underneath in case it gets windy.

Aloud statement

Now that it’s jacket season, make a statement with yours by going for a cool patchwork style. Wear this eye-catching piece with simple khakis and sneakers to let it have its moment in the spotlight.

Add glitter

You don’t have to wait until the holidays or New Years Eve to wear sequins. In fact, a pair of sparkly boots adds just the right amount of pizzazz to a neutral ensemble.

Impactful details

Don’t underestimate the impact an oversized collar can have on an outfit. Wear it under a clean jacket and all eyes will be on the cool details.

Awesome rocket

Flare jeans are having a big time, so consider adding the funky silhouette to your jeans line. Wear the bottom with everything from chunky loafers to simple white sneakers.

Western ambiance

Welcome to fringe season. Embrace the offbeat trend by investing in a fringed jacket this fall. Pair western outerwear with animal print pants for a surprisingly chic combination.

Clogging around

Whether you like them or not, clogs aren’t going anywhere. If you don’t like the traditional wooden silhouette, try a leather or rubber iteration.

Safe Combo

A dress and sneakers outfit is a great duo to have on hand in case you are unsure of what to wear. Add some dainty jewelry and you have an outfit ready for just about an activity,

Have a little fun

Fashion shouldn’t be too serious, so try to have fun with your fall outfits by playing with mushroom and flower print pieces. The more original symbols you add into the mix, the better.

An easy piece

ICYMI: A bicycle body shorts are a must-have item this season, according to fashion girls. Ultimately, they’re the perfect layering piece for a blazer or long jacket.

Classy grocery run

Shopping for groceries while you are half asleep? You can keep your boxer shorts cozy for the occasion. To make them appropriate outside of the house, don a crew-neck 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 is just what you need in your life. You’ll instantly illuminate every room you enter.

Minimalism at its best

An all-white outfit is always a good idea, same after labor day. For those who like a splash of color, slip on a shiny 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 the Christopher Esber iteration below. It certainly won’t be a one-off look.

Bring out the leather

The moment you’ve all been waiting for is now: leather season. Style wise, you can’t go wrong pairing black leather pants with a matching turtleneck.

Classic Combo

If in doubt, put on your white tank top and jeans. But instead of strappy sandals, pull out your favorite fall boots to get the outfit approved for cold weather.

Updated accessories

Take inspiration from the spring / summer 2021 catwalks in Copenhagen and swap your glitzy necklaces for a silk scarf. The easy styling technique really packs a punch in a simple cardigan and skirt as shown below.

Canadian Tuxedo 2021 Edition

Ah, an old but a goodie – the Canadian tuxedo. Give the signature style a 2021 touch by opting for loose dividers.

Back to dressing

Do you miss the feeling of putting on a dress or a skirt? Change that up by bringing out a luxe midi skirt, even if you don’t intend to leave the house. The bottom is a comfortable alternative to your work pants.

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