Anytime when season changes, it can cause confusion around the right thing to wear. In September, it’s not cold yet, but you may feel a bit chilly – the in between zone that isn’t the easiest to dress for.
The best outfits for September weather should have a simple layering to keep you warm outside, but is easy to put on and take off so that you can switch to a warmer indoor temperature. Underneath the layering, you can wear something either causal like T-shirt and jeans or polished like a long sleeve dress, depending on the occasion you are dressing for.
Table of Contents
The wardrobe staples
Here are the 9 staples for the September weather:
- Suede booties
- Tall boots
- Motor jacket
- Trench coat
- Sweater skirt
- Denim jacket
- Faux leather skirt
- Merino wool sweater
- Midi skirt
- Jeans
With the above chilly weather staples, here is some of the best style ideas on what to wear in September weather. You can use these outfit formulas to create simple yet chic outfits for everyday wear or dressed up looks, anytime its in the 60s outside.
Wide leg jeans
Starting with a classic outfit combination for the September weather you can always count on.
You can pair the jeans with any top in your closet such as a t-shirt (graphic, striped, solid, etc) and complete it with a chic layering piece like a blazer.
Suede booties
The suede booties is the staple for chilly weather in the 60s.
Layering a jacket or sweater over the t-shirt adds just enough warmth to the outfit, without making you feel too hot. Have fun with the layering element of this look. Since you’re wearing jeans and a t-shirt, the layering piece gives you a chance to really showcase your personal style.
Tailored blazer
If you like a polished look, then go with a well tailored outer layer like the blazer, this can take you to any occasion that calls for “smart casual” dress code. If you want a more relaxed look, then swap the blazer with a relaxed fit cardigan.
A simple outfit like this also makes it easy to accessorize. Add a belt, necklace or earrings to elevate the look into a less than basic one.
Trench Coat
This is a classy and simple outfit if it’s 60s outside. The key components are the trench coat and the boots.
Trench coats are always a great choice for September weather, especially if it’s going to rain. But they aren’t only functional for rainy days, because of their lightweight they’re an obvious choice when you just need a light layer.
You have many options for the under layer. Styling a trench coat with a white shirt keeps your look classic and easy to wear. However, if you want to spice up your look, you can swap the white shirt out for a graphic tee, printed shirt, or even a cropped tee.
Cropped pants
For those days when you want a modern twist to your look, cropped pants are perfect! Cropped pants give you the comfort and coverage of long pants.
The slight difference in length really changes the entire vibe of an outfit, though. Since cropped pants are such a big trend right now- it’s a fun option to try this year. Style your cropped pants with a shirt, like a white button down shirt, and a trench coat.
Ankle boots
Boots are a critical element in this outfit. They can keep you really warm in the September weather.
Depending on the color of your pants, you can choose the best colors for your boots. If you are wearing white or light color pants like me, then a pair of beige or brown tall boots are a great option.
Sweater skirt
Sweater skirts are another wardrobe staple for chilly weather like the 60s. They keep you warm, especially when you go with longer length such as a midi or a ankle length, and they’re easy to wear.
To keep the sweater skirt feeling appropriate for the weather, throw on your favorite denim jacket. It gives you that layering element, while still keeping things casual and cute.
Denim Jacket
Adding a simple layer, like a denim jacket, is a great way to transition your summertime outfits into the fall and springtime.
As for the shoes, you can go with anything. If you want a warmer outfit, pair it with tall boots, otherwise, you can also wear this outfit with flats for a comfortable daily look.
Midi Skirt
Motor jacket is another staple for the fall or spring, and they are one of the best options for September weather. The reason is a classic motor jacket is typically made of leather or suede, which is great when it gets colder, but meanwhile they are cropped length so they will not make you sweat.
Midi skirts aren’t just a huge trend right now, they’re also a great skirt style to wear for September weather. The added length can make a huge difference when dressing for the weather that is chilly.
Moto jacket
If you want to wear a shorter dress, you’ll want to pair it with a suede or leather motor jacket to make sure you’re warm enough.
The motor jacket gives you the flexibility to pair this look with a wide variety of shoes such as flats, booties or pumps! There really are a lot of shoe options that can work with this type of outfit – depending on the occasion you’re dressing up for.
Jumpsuits
Jumpsuits are not only stylish, but also perfect for the September weather. If you live in low 60 degree weather, opt for long sleeves to fully cover your arms for those colder mornings and nights.
Tall boots
If you prefer a shorter length, you can still wear a mini (or shorter) skirt when it’s 60 or 70 degrees out without freezing. The key is to make sure you’re adding the right elements in combination to the skirt. I recommend pairing a shorter skirt with taller boots when it’s chilly outside. The added length of the boot covers more of your leg, which is key to keeping you warm.
Camel Cardigan
Layer your shorts with a cardigan will give you a relaxed yet warm outfit, when it’s chilly out. These heavier top layers are going to further assist in transitioning a short bottom to being appropriate for cooler weather.
Merino pullover
A merino wool sweater is a must have when the weather falls to the 60s. Typically these are made of thinner merino wool, which can keep you warm but will not feel like too hot.
Leather skirt
Faux leather or faux suede skirts are a perfect choice to wear with the merino wool sweater for a chic outfit. Of course, you can opt for real leather or suede, if your area is colder. If you live in a warmer area, then a faux leather or suede fabrics are enough to keep you warm.
I suggest styling your sweater in a half tuck into the skirt so your waist and shape isn’t lost in the outfit. This is especially key when you’re wearing a longer, midi skirt.
Complete the look with closed toed shoes, these will also ensure you’re warm enough – September tends to be a bit too chilly for open toed options.
Midi Dress
You can definitely style a dress for September. I suggest opting for a midi dress, the added length gives you a bit more coverage so you’ll be warmer since it’s still a bit on the chilly side. Add a blazer or cardigan over your midi dress for additional warmth and style. If you want to add a bit of edge to the look, you can replace the blazer/cardigan with a leather moto jacket.
Khaki pants
Khahis are very versatile pieces that you can for sure wear in September. For a chic outfit, go with a high waisted khaki pants and pair with a fitted shirt.
Sweatshirt
Sweatshirts are something you can wear year-long, and you can turn them into stylish outfit if you pair them with a shorter skirt!
Varsity jacket
A light weight jacket can come in handy, when the weather is up and down. Go with your favorite color, and pair with a pair of black pants- you are ready to go!
White button down
A button down shirt is a wardrobe staple you can wear any season, and of course you can easily turn them into a September outfit when you pair them with a light weight skirt.
Off the shoulder long sleeve blouse
Off-the-shoulder is a chic design that you can always count on when you want to look feminine, and you’ll love the long sleeve option if you prefer to have your arms covered during the chilly times of the day.
Pastel pants
If you are looking for a warm weather outfit for September, you can’t go wrong with pastel colors! The easiest way to wear these is to put on a pair of wide leg or straight leg pants in light pastel color and pair with a simple top like a white T-shirt.
Long sleeve lace blouse
You’ll love how stylish yet functional a lace blouse is when the weather is in the 60s. Because they are lightweight, they will make sure you won’t be too hot when the sun is out. Opt for long sleeves if you want to keep yourself warm during the chilly hours of the day.
All of these outfits give you a general outfit formula that you can build from to create your own unique outfits. Mix and match different pieces in your wardrobe, that may be similar to what I’ve mentioned above. Even if you don’t have the exact items, I’m sure you have something similar that will allow you to create an outfit that’s just as stylish!
Donna Abrahams says
I love your classy, sexy, proportional style recommendations! Can you tell me if a floor length maxi sweater will ever be fashionable for petite women? I freeze in the wintertime & haven’t been able to find a heavyweight, button up, maxi sweater in years! Of course with covid, I could just wear robes at home & stay safe, but I prefer to be warm when I do need to go out for medical appts. Thanks for any help you can offer!
Chi says
Hi Donna- maxi length almost always work for petites! The key is to choose one that has waist definition (so that it wouldn’t look like a sleep bag on us), and also shows your ankle (always show wrist and ankle when you can)!