A Complete Guide to Summer to Fall Transition Outfits

Even though the weather is still summery, most of us are already daydreaming about fall. It’s without a doubt my favorite season to dress for, but the transitional weeks can feel a little wobbly when it comes to what to wear.

Transitional style is something I’ve only come to enjoy in the past few years. I used to think I needed to start from scratch, but I’ve found the key is tweaking summer favorites to make them feel fresh and practical while giving a nod to autumn.

With that in mind, I put together this transition style guide to help you navigate the shift with a little more ease. See below for summer to fall transition outfit ideas, tips for creating your own transitional looks, and a list of wardrobe essentials for this time of year.

fall transition outfit with sweater, tank top, and jeans

Summer to Fall Transition Outfits

Here are six transitional looks that will allow you to feel both fall like and comfortable in the current weather.

Shorts Swap

I love to swap out my linen shorts and cutoffs for leather, khaki, or fall-toned shorts this time of year. Pair them with a knit tank, which lends more of a fall feel than a cotton one, and finish the look with sandals or low heel booties and a lightweight blazer.

The Extra Layer

I wear something similar to this on repeat in September because it’s as simple as adding a layer to a favorite summer look. Start with relaxed straight jeans (I love these), a tank, and sandals, then layer a thin cashmere sweater or cardigan over your shoulders. If you’re looking to refresh your sweater collection, I shared a few of my favorite brands for knits here.

Long Sleeve Dress with a Boot

Dresses are bar none the easiest to style in transitional looks. A seasonal shoe (ankle, mid-calf, or knee high boots) and bag is all you need to set the fall tone. Long sleeve dresses work especially well, but you can layer a sleeveless dress under a moto jacket or blazer to pull the look together and keep warm.

Layered Summer Dress

Knit dresses have grown on me in a major way and this one turned out to be one of my best purchases all summer. Dresses like this transition easily with a layer and closed-toe shoe. Go casual with sneakers and a denim jacket, or style it for work with a blazer and pump like I did here. You could take this concept further into fall with tights, knee-high boots, and a heavier layer.

Button Down or T-Shirt Dress

I think it’s safe to say most of us have a button down in our wardrobes, whether in the form of a shirt or shirt dress. To give either a dose of fall, layer a pullover (worn properly or draped over your shoulders) and grab some booties. If you’re working with a shirt, pair relaxed denim with an inseam that hits just below the top of the shoe.

For the Office

Wide leg, bootcut, and trouser-style pants are still trending, and the great news is they’re incredibly easy to style for early fall business casual settings. Try pairing yours with an elevated tank and a belt. The sleeveless top gives a fresh feel, but layers well under a blazer.

summer to fall transition outfit with flat mules

How to Transition Your Summer Outfits to Fall

When you’re considering what to wear in a summer to fall look, there are a few areas of focus that help tell the between-season story in a practical way.

1. Opt for Darker Colors

Colors communicate the season, and moodier hues like burgundy, rust, black, and camel scream fall. Look for breathable fabrics to keep you comfortable in lingering heat. I shared a few trending hues in the fall 2022 trends guide.

2. Incorporate Layers

A lightweight layer such as a denim jacket, anorak, blazer, cardigan, or cashmere sweater will be your best friend for transitional looks. Play around with the styling until it feels right to you. Try it draped over the shoulders, worn properly with the sleeves rolled up, tied around the waist, etc.

3. Swap Your Shoes

Sandals work in any of the looks above, but at some point it feels right to transition to closed-toe shoes. Mules, ballet flats, and loafers offer the simplicity of sandals without exposing the toes. Sneakers and low- to mid-shaft boots are great fall transition shoes as well.

4. Accessories in Fall Tones/Textures

Swapping in autumnal accessories, like suede and leather bags and darker hair accessories, belts, and scarves, bring a fall feel front and center without adding heat. A darker nail polish is also an affordable way (I love this color) to hint at fall.

5. When In Doubt, Denim

Jeans are the first thing that comes to mind when I think fall style. I covered fall 2022 denim trends here, but you can style almost any pair with summer favorites (tank tops, white tees, summer blouses) and fall accessories for a transitional look.

Fall Transition Outfit Checklist

As promised, here’s a summer to fall transition wardrobe checklist. These are 11 pieces to audit your closet for that help summer looks flow into cooler weather.