A Simple Guide for Summer to Fall Transition Outfits

These summer-to-fall transition outfits are so easy, you’ll never struggle with what to wear this time of year again!

It’s almost that time of year when the weather starts to cool down, but it’s not quite cool enough for thick sweaters and cozy scarves. I always find that figuring out what to wear during the transition from summer to fall is a challenge. The day might start off cool, but by noon, you could be sweating. Or one day it’s a comfortable 65 degrees, and the next it’s 80!

I know the urge to throw on knee-high boots and your favorite fall accessories is real, but that might not be the best choice during this transitional time. You don’t want to be stuck sweating in those boots all day! You need layers.

But how do I layer my outfits for the transition from summer to fall? Well, I’m glad you asked. It’s actually really simple. I like to have a few outfit combinations on hand when I’m not sure what to wear this time of year.

P.S. If you need to add to your wardrobe for fall, places like Target and H&M always have affordable options!

Before we get to my summer-to-fall outfits, let’s talk more about getting your wardrobe ready for the upcoming months! 

Summer to Fall Transition Outfits

What month should you start shopping for fall clothes? 

This is kind of a personal question since you may or may not need any additions to your wardrobe for fall. Typically, I like to assess my closet in July. I take a look at all of my pieces and see what needs to be donated or thrown away. If I notice gaps in my wardrobe, like needing a few new white tees, I add them to a list. I like to use my capsule wardrobe checklist to make it easier to figure out what I need each season.

Once I know what I need, I start shopping for new pieces in July and August. This is perfect because Nordstrom always has their Anniversary Sale in July. Their sale is great because you can get discounts on new arrivals for the fall.

Missed the sale? No worries. Nordstrom Rack always has great pieces at affordable prices, and this time of year, they have tons on clearance.

What do you need in your wardrobe for the transition from summer to fall? 

What you need in your wardrobe will vary based on your location and personal preference. Below are some items I like to have because they are versatile and easy to style.

Don’t feel like you need to go out and purchase each item. If you don’t like wearing midi skirts, then skip that piece! This is just a suggestion based on my capsule wardrobe. 

• Summer Dress
• Linen or lightweight Blazer
• Lightweight sweater
• Denim jacket 
• Sneakers
• Graphic Tee
• Plain white tee
• Midi Skirt 
• Denim mini skirt
• Relaxed denim jeans 
• Sandals 
• Booties
• Leather Jacket 
• Long Sleeve Top
• Cozy knit cardigan 
• Something suede (boots, jacket)
• Loafers 
• Romper / Jumpsuit
• Mules 

What are the styles trending for fall?

If I know that I have the basics in my wardrobe, then I will shop for some of the trendier items. Here are a few of the trends that are going to be popular this fall! 

• Classic blazers 
• Lingerie Dressing
• Sequins
• Color combinations
• Faux Fur
• Lace
• Naked dressing (not really wearable. Maybe with something underneath)
• Slouchy bags
• Leopard print
• Loafers (more of a staple)
• Trendy statement belts
• Shades of dark brown
• Pencil skirts

Let me know in the comments if you’d like to see a blog post on any of these trends for fall!

When can I start wearing fall clothes?

Whenever you feel like the weather allows! If it’s still too hot for fall clothes, then try incorporating fall shades. For example, wear a brown floral top with your favorite mom shorts. Or try a dark olive dress with sandals! 

Outfit Transition Ideas for Summer to Fall

Ok, now that we have the basics covered, it’s time for a few summer-to-fall transition outfits! I tried to make these outfits versatile so that you could wear them in almost any climate. If it gets hot throughout the day, you can always take off your cardigan or jacket! 

Denim shorts + Basic tee + Lightweight Cardigan + Sneakers

You already have your shorts from summer. Why not get as much use out of them as possible? All you need to do is add a cardigan and some comfortable sneakers.

Dress + Sneakers + Denim Jacket 

Dresses are a staple in summer. I usually don’t want to think too much about what to wear when it’s hot, so I throw on a dress. There’s no need to pack away your summer dresses when it gets closer to fall. Just throw on a denim jacket and some sneakers for a casual look.

Dress + Boots

Mix something edgy with something feminine for a fun twist. Keep wearing your summer dresses in the fall. Just add a pair of combat boots for an edgy look. If it gets a little chilly, wear your favorite jacket over top.

Jeans + Crop Top+ Sandals

You can’t go wrong with a pair of blue denim jeans, a cute top, and sandals. You can even wear suede shoes in summer. This is an easy look for warmer fall days.

Shorts + Bodysuit + Blazer + Sneakers

A matching blazer and shorts set is such an easy look for fall. If you don’t have a blazer, I highly recommend grabbing one. This set is actually a Target find from last summer. Yes, I am absolutely an outfit repeater. I like this outfit because you can take this formula and apply it to any shorts and blazer combo. It doesn’t have to be a matching set.

Mini Skirt + Booties + Top

As a petite woman, I couldn’t be happier about the mini skirt trend. At 5ft tall, I find it easy to find a short skirt that isn’t too short. If you’ve been wearing a mini all summer long, there is no reason to stop. Just warm it up with a pair of booties and a tee. If it gets even cooler outside, add a denim or bomber jacket.

Jumpsuit + Leather Jacket + Sandals

Jumpsuits are great because they are easy to style. Like summer dresses, you can take a jumpsuit, add your favorite leather or denim jacket, and you’re ready for transitional weather.

Leggings + Graphic Tee + Denim Jacket

If you want to be super comfy but still look stylish, try faux leather leggings. You can bring a jacket with you and ditch it if it gets too hot.

Romper + Booties

Rompers are similar to jumpsuits, but I wanted to give you another option for fall. You can go for long sleeves or short sleeves and just add your favorite jacket on top. If it’s too hot for booties, swap them for sandals.

Mini Skirt + Loafers + Denim Jacket

This outfit is perfect for in-between days when the sun is shining, but it’s still a little cooler. I paired my denim mini skirt with a denim jacket I thrifted and some white loafers. This look is perfect for late August and early September.

Jumpsuit + Sandals + Outerwear

This jumpsuit has been a staple in my wardrobe for years. It is a great transitional piece, and you can easily dress it up or down. When it gets a little chilly, swap the sandals or sneakers for closed-toe heels and add a denim or leather cropped jacket.

Summer Dress + Knee High Boots

At first, I wasn’t sure about black knee-high boots with this cream summer dress, but I actually think it’s unexpected and edgy. If it’s too much of a contrast, a pair of brown boots works wel,l too. As always, you can add a jacket on top for more warmth.

Jeans + Brown Tie Front Top + Sandals

At the end of summer, I love to start incorporating more fall colors, even if the weather is still a bit warm. I’m wearing jeans because it isn’t quite warm enough for shorts, but it’s still too warm for long sleeves. This day was warm enough to skip a cami under the tie front top, but if it’s a little chillier, a cami in the same color would be perfect.

As you can see, these summer-to-fall transition outfits are all about taking your basic pieces and adding layers. It’s really simple, and you can apply this to any seasonal transition.

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