September Fall Outfits: A Month of Style

As the lazy days of summer give way to the crisp embrace of autumn, September emerges as a month of transition – not just in nature but in our wardrobes. The ninth month of the year brings a unique sartorial challenge: how to dress for days that begin with a chill, warm to a summery embrace, and then cool again as evening falls. It’s a time when the fashion-forward must be prepared for anything, from lingering summer heat to the first whispers of fall’s cooler temperatures.

The Art of September Dressing

September is a month of contrasts, and your wardrobe should reflect this. It’s a time to embrace layering, play with textures, and gradually introduce autumn’s rich, warm colours while still holding onto the lightness of summer. The key to mastering September’s style lies in versatility and preparedness.

As we journey through the month, we’ll see a gradual shift from summer’s light, breezy fabrics to the more substantial materials of fall. Early September may still call for shorts and sundresses, while late September might require cosy sweaters and waterproof jackets. This transition offers a unique opportunity to get creative with your wardrobe, mixing and matching summer and fall pieces to create practical and stylish looks.

In this article, we’ll explore 60 outfit ideas – 30 for women and 30 for men – that span September. We’ve got you covered, from sunny days perfect for outdoor brunches to rainy afternoons ideal for museum visits. Each outfit is designed with the day’s weather in mind, ensuring you’ll be comfortable and chic no matter what September throws your way.

So, let’s dive into a month of fall fashion, exploring how to dress for every occasion and September’s weather conditions. Whether you’re heading to the office, enjoying a weekend getaway, or running errands around town, you’ll find inspiration for both seasonally appropriate and effortlessly stylish outfits.

60 September Outfits for Every Occasion

September 1 (Sunny, 75°F/64°F)
- For Her: A breezy sage green skirt paired with an ivory top makes a perfect ensemble for a late summer picnic in the park.
- For Him: Beige shorts and a light blue polo create a casual yet put-together look for a day of outdoor activities.
September 2 (Sunny, 79°F/64°F)
- For Her: A terracotta jumpsuit accessorized with a coral necklace is ideal for an al fresco dinner with friends.
- For Him: Olive shorts and a grey henley offer comfort and style for a casual weekend barbecue.
September 3 (Sunny, 88°F/70°F)
- For Her: A vibrant floral sundress is perfect for a sunny day at an outdoor music festival.
- For Him: Light khaki shorts and a sky-blue tee make for a relaxed, comfortable outfit for a day at the beach.
September 4 (Sunny, 90°F/77°F)
- For Her: High-waisted mustard shorts and a white crop top are great for a hot day of sightseeing in the city.
- For Him, Breathable grey pants and a forest green tank are ideal for an intense outdoor workout.
September 5 (Sunny, 90°F/79°F)
- For Her: A coral maxi dress with side slits is perfect for a late summer wedding.
- For Him, Navy quick-dry shorts and a light green polo are great for a round of golf on a warm day.
September 6 (Sunny, 91°F/81°F)
- For Her: Teal palazzo pants and an ivory blouse make for a chic office look on a hot day.
- For Him: Stone grey shorts and a pale yellow linen shirt are perfect for a business casual meeting in a non-air-conditioned venue.
September 7 (Sunny, 93°F/81°F)
- For Her: A coral pink romper is ideal for shopping in an outdoor mall.
- For Him: Light beige linen pants and a navy tank top are perfect for a hot day at an amusement park.
September 8 (Sunny, 86°F/77°F)
- For Her: A burnt orange skirt and white crop top, paired with a light wash denim jacket, transition well from a day at the office to evening drinks.
- For Him: Olive Bermuda shorts and a gingham shirt work well for a casual Friday at the office, extending into after-work socializing.
September 9 (Cloudy, 82°F/73°F)
- For Her: A polka dot wrap dress in deep green is perfect for a cloudy day at the farmer’s market.
- For Him, Dark khaki chinos and a maroon polo are great for a wine-tasting event on an overcast day.
September 10 (Cloudy, 75°F/73°F)
- For Her: Rust-colored wide-leg crops and a cream blouse make for a stylish outfit for a gallery opening.
- For Him, Medium wash jeans and an olive henley are perfect for a casual dinner with friends.
September 11 (Cloudy, 77°F/72°F)
- For Her: A navy A-line skirt and soft pink top are ideal for a day at the office.
- For Him, Dark olive khakis and a burgundy tee work well for a casual business meeting.
September 12 (Cloudy, 81°F/70°F)
- For Her: A chambray shirt dress is perfect for running errands or casual meetings.
- For Him, Rust-colored shorts and a patterned white shirt are great for a cloudy day at an outdoor café.
September 13 (Cloudy, 77°F/73°F)
- For Her: Mustard culottes and a black sleeveless turtleneck make for a chic outfit for a theatre matinee.
- For Him: Dark wash jeans and a charcoal V-neck are perfect for a casual date night at a cosy restaurant.
September 14 (Cloudy, 75°F/68°F)
- For Her: A burgundy midi skirt and floral blouse, topped with a trench coat, are ideal for a day at the office that might include client meetings.
- For Him, Navy chinos and a forest green henley work well for a casual Friday at work.
September 15 (Cloudy, 70°F/63°F)
- For Her: Straight-leg jeans and a dusty rose sweater are perfect for brunch with friends.
- For Him: Dark jeans and a light blue button-down make for an excellent casual wedding rehearsal dinner outfit.
September 16 (Cloudy, 75°F/63°F)
- For Her: An emerald wrap dress is ideal for a day of museum hopping.
- For Him: Beige khakis and a deep purple polo are perfect for a family gathering or informal celebration.
September 17 (Cloudy, 75°F/64°F)
- For Her: Olive cropped pants and an ivory top make for a comfortable yet stylish outfit for a day of travel.
- For Him, Stone grey shorts and a rust-coloured tee are great for a cloudy day at an outdoor sporting event.
September 18 (Rainy, 66°F/68°F)
- For Her: Dark wash skinny jeans and a teal sweater, paired with a trench coat, are perfect for a rainy day at work.
- For Him: Charcoal water-resistant pants and a burgundy shirt, topped with a rain jacket, make for a practical yet stylish rainy-day outfit.
September 19 (Cloudy, 72°F/63°F)
- For Her: A navy polka dot dress layered with a mustard cardigan is ideal for shopping or lunch with friends.
- For Him: Rust-colored chinos and a grey henley are perfect for a casual business meeting or networking event.
September 20 (Cloudy, 72°F/61°F)
- For Her: Black ponte pants and a deep purple blouse make for a polished look for a day at the office or an important presentation.
- For Him, Dark jeans and a forest green gingham shirt are great for a dinner date or an evening out with friends.
September 21 (Cloudy, 70°F/63°F)
- For Her: A rich brown midi skirt and cream turtleneck create a sophisticated autumn look for a day of client meetings.
- For Him: Dark olive khakis and a burnt orange sweater are perfect for a fall-themed outdoor event or harvest festival.
September 22 (Cloudy, 68°F/63°F)
- For Her: Medium wash jeans and a burgundy long-sleeve tee, topped with a dark denim jacket, make for a comfortable outfit for apple picking.
- For Him, Rust-colored chinos and a navy polo are ideal for a casual Friday at the office or an informal dinner party.
September 23 (Rainy, 57°F/61°F)
- For Her: Water-resistant olive pants and a mustard sweater, paired with a teal rain jacket, are perfect for a rainy day exploring a new city.
- For Him: Dark wash water-resistant jeans and a burgundy thermal, topped with a rain jacket, make for a practical outfit for a wet day of errands or casual outings.
September 24 (Rainy, 63°F/61°F)
- For Her: Black leggings and an oversized oatmeal sweater, paired with rain boots, are ideal for a cosy day at home or a quick coffee run in the rain.
- For Him: Charcoal water-resistant pants and a forest green fleece make a comfortable outfit for a rainy day hike or outdoor activity.
September 25 (Rainy, 59°F/64°F)
- For Her: Dark wash jeans and a deep purple long-sleeve shirt, topped with a mustard raincoat, are perfect for a rainy day at work or running errands.
- For Him: Khaki water-resistant chinos and a rust henley, paired with a navy rain jacket, are great for a casual business meeting on a wet day.
September 26 (Rainy, 61°F/59°F)
- For Her: Charcoal water-resistant leggings and a deep red tunic sweater make for a cosy outfit for a rainy day at a bookstore café.
- For Him, Medium wash water-resistant jeans and a forest green thermal are ideal for a casual day of indoor activities on a wet day.
September 27 (Rainy, 64°F/54°F)
- For Her: Black skinny jeans and a camel turtleneck, topped with a teal rain jacket, are perfect for a day of museum visits on a rainy day.
- For Him: Olive water-resistant pants and a grey fleece make a comfortable outfit for a rainy day at an indoor sporting event or casual gathering.
September 28 (Rainy, 61°F/57°F)
- For Her: Navy water-resistant pants and a burnt orange sweater, paired with a tan raincoat, are ideal for a rainy day at work or parent-teacher conference.
- For Him: Dark khaki water-resistant chinos and a burgundy shirt, topped with a rain jacket, make for a bright casual look for a rainy business meeting.
September 29 (Rainy, 61°F/61°F)
- For Her: Dark grey leggings and a deep purple long-sleeved dress, paired with a forest green rain jacket, are perfect for a rainy day shopping trip or a casual outing.
- For Him: Dark wash water-resistant jeans and a rust thermal, topped with an olive rain jacket, are great for a wet day of running errands or meeting friends for coffee.
September 30 (Rainy, 64°F/59°F)
- For Her: Medium wash jeans and a dusty blue sweater, paired with a khaki trench coat, make for a stylish outfit for a rainy day at work or evening plans.
- For Him: Charcoal water-resistant pants and a deep green polo, topped with a burgundy rain jacket, are ideal for a casual Friday at the office or an informal dinner on a rainy evening.

Mixing and matching these outfit ideas, you can create a versatile September wardrobe ready for anything the weather might bring. Remember, layering is the key to fall fashion, so don’t be afraid to combine pieces creatively to stay comfortable and stylish throughout the day.