How to Create Easy, Transitional Outfits like a Pro: Tips, Tricks & Hacks

This week, I’m helping you create easy and cute outfits to go from summer to autumn.

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This post will teach you how to create cool transitional outfits to go from summer to autumn.

Autumn is finally here! (Cue the Gilmore Girls intro song.) The leaves are changing and so are our closets.

For a lot of us it’s exciting to finally break out our sweaters, coats, and boots. But the weather is at a point where it hasn’t exactly caught up with our excitement.

That’s where transitional outfits come in, and that’s where we’ll be focusing our attention today.

But, what *is* a transitional outfit?

In the early weeks of fall, we all experience transitional weather. It might be a bit chilly in the morning, hot in the afternoon, and cold at night. It might even rain, you never know.

All these changes make it hard to get dressed in the morning.

A transitional outfit is a look you create to deal with all the different weather possibilities that arise when we go from summer to autumn. These outfits can be tricky to create since, by design, you’re dressing for multiple types of weather at once.

How to Create a Transitional Outfit: Tips, Tricks, & Hacks

Here are some of my favorite ways to be prepared for everything while looking cool:

  • Light layers – Create outfits with multiple, thin layers that you can take on and off through the day as the weather requires.
  • Textures and fabrics are your friends – To keep wearing your favorite summer items, mix them with items made from warmer fabrics and especially textured options like suede, velvet, and corduroy.
  • Simple switches – To create transitional looks, take your summer outfits and make substitutions. For example, add an oversized sweater on top or swap your sandals for boots.

How to Create Transitional Outfits Like a Pro: A Fashion Guide

Jeans + T-shirt, Easy – Outfit #1

One of the most basic year-round outfit formulas is jeans and a T-shirt.

During summer, we usually wear this combo with cute heels, sandals, or flats. In the fall, we can add layers and warmer fabrics.

For the easiest transitional look, let’s add autumnal textures to the outfit and switch our summer shoes for warmer ones.

Here, I started with a black graphic t-shirt and a pair of high-waisted jeans. Then, I added a burgundy, faux-leather blazer. Finally, I accessorized with a black belt and opted for black sock booties.

The great thing about a jeans and tee combo is that it’s easy to make it suitable for cold weather by adding warmer items. While I could have added any blazer, I chose the burgundy for its warm, rich shade that is both very autumnal and very trendy right now.

Trousers + Tank Top, Easy – Outfit #2

One of my favorite outfit formulas is a tank top and a pair of sleek trousers. I think it’s one of the best ways to be comfortable, and it’s easy to take from day to night.

Similarly, this combo is easy to take from summer to fall.

For this example, I started with a simple white tank top. Then, I added black pinstripe trousers. Since I was working with such a neutral base, I added a red, oversized sweatshirt for a pop of color. Finally, for shoes, I chose red and white sneakers to bring the whole look together.

This outfit can look different depending on your style. Personally, I like pops of color in my outfits, but you could go neutral or add a more textured jacket or sweater.

This is obviously best for the warmer days of fall, but it’s a simple formula that you can keep adding layers to as the weather gets colder. The same tips apply: make a simple replacement, either the shoes or the top, add another jacket or overshirt, etc.

Long Cotton Skirt + Sweater, Medium – Outfit #3

Now, what about the items that we specifically love during summer, like our linen pants, cotton skirts, and flowy dresses?

One of my go-to summer looks is a long cotton skirt and a tank top, and it’s simple to transition that combo to fall.

For this example, I made a simple switch to take the outfit into fall. I started with my favorite long, white cotton skirt. Then, instead of a tank top or t-shirt, I layered on a mustard yellow, cable-knit sweater. For shoes, I wore a pair of brown riding boots and accessorized with a matching belt.

The great thing about midi and long skirts is that they look amazing with all types of boots and with warmer tops. And, if it gets even colder, you can wear this far into the fall season by adding a coat and even thermal tights underneath.

Long Dress + Ribbed Top, Medium – Outfit #4

Flowy dresses are also a summer favorite.

To wear these in the fall, you could do the same thing I did with the skirt — add a chunky sweater or oversized sweatshirt and boots. But, there are other ways of layering if it isn’t that cold outside.

First, start with your most comfortable, flowy summer dress. For me, that’s any long, loose cotton dress. In this example, I chose a light pink loose dress I made. I added a green, long-sleeved top underneath. Since this is for the warmer days of fall, instead of boots, I wore a pair of green and pink sneakers.

Any flowy, sleeveless dress can work year-round if you know how to layer. You can wear a t-shirt, a long-sleeved top, a turtleneck, and even a thermal top underneath, and you can layer sweaters, shirts, sweatshirts, and even capes over top.

Mini Skirt + Knit Top, Difficult – Outfit #5

Now, we’re getting to the most challenging items to transition. Among them are mini skirts and shorts, especially if they’re made of a summery fabric.

Let’s start with a mini skirt.

For this example, I started with an off-white, pleated mini skirt. During the summer, I would wear it with floral blouses and bright tops, so I switched it up and added a brown knit top. Then, I put on a pair of brown knee-high boots. Finally, I layered on a brown, oversized blazer.

Again, this is a look for the warmer side of transitional weather, so I’m not wearing tights for this example. As it gets colder, I’d add tights and a long-sleeve top. But for this type of fluctuating weather, I prefer to have layers that I can easily take on and off.

Shorts + Baby Tee, Difficult – Outfit #6

Finally, what’s more summer than a pair of shorts and a baby tee? Especially if they’re linen or cotton.

Again, adding light layers, choosing jewel tones, autumnal fabrics and patterns will take you from summer to fall.

For our final look, I started with a pair of plaid, high-waisted shorts. Then, I wore a white baby tee and layered on a navy-blue cardigan. For shoes, instead of sneakers or sandals, I chose a pair of red cowboy boots.

Plaid shorts work particularly well for transitional outfits. These shorts are burgundy and blue, so they already have an autumnal color palette, but any plaid shorts you have can be styled for fall.

I know red cowboy boots are not for everyone, so brown riding boots or over-the-knee boots would also go with this outfit formula. Personally, I love cowboy boots, so I try to break them out every chance I get.

What Do You Think?

Would you wear any of the outfits? What’s your favorite outfit formula right now? Do you have any recommendations for this time of year? Do you have any styling questions?

Let us know in the comments below!

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