Summer to Fall Transition Outfits | A Complete Guide

Lulus Fall Transition Outfit

The seasons are changing, and it’s time for our style to change with the weather. However, during those few delicate weeks where summer has begun to fade but fall isn’t yet here in full force, it can be tricky to know what to wear and how to transition gracefully within seasons. Fall transition outfits are actually some of my favorites to put together, because I love being able to get a few final wears out of my favorite summer pieces while breathing new life into them through some autumnal touches.

If you find yourself struggling with knowing what to wear in the days before the new season hits full force, don’t worry – I have you covered. I have so many different transitional outfit ideas for you to incorporate into your day to day style, and I’m excited to show you how much fun the summer to fall transition can be. If you’ve been looking for some inspiration, keep reading for my best tips to make the seasonal transition an effortless one, along with my recommendations for the pieces that are essential during these in-between days.

Fall Transition Outfit


Do you feel like you’ve lost your go-to looks as the air has begun to take on a chill? Keep reading for my top swaps to keep you looking your best, no matter how unpredictable the weather may be.

LAYER YOUR Summer Dresses

I’m always a little sad when it comes time to move all of my summer dresses to the back of the closet for the season. As we transition to the fall, I like to get a little extra wear out of my summer dresses by layering them. It’s such an easy transition to make – just throw your favorite sweater overtop the dress and pair it with a closed-toe shoe like ballet flats, and you’re good to go!

There are so many options for different styles, too – you can go for a sportier look by pairing the dress with a denim jacket and some sneakers, or you can go more elevated with a chic blazer and wedge bootie or pump. You can even carry your dresses even further into the cooler months by layering more heavily with a thicker coat, full boots, tights, and scarves.



Who says shorts have to stay tied to the summertime? While I tend to pack away my beachy linen shorts and ratty denim shorts once the autumnal months hit, that doesn’t mean there aren’t still days where I want to make shorts a part of my look. Instead, I lean towards leather shorts, or shorts that are deeper tones reminiscent of fall. You can pair these with some great neutral pieces – I like to add a bit of texture to the top to accentuate the fall feel – and finish the look off with any range of shoes, from stylish sneakers to slingback sandals.


BASIC Button Down

Whether it’s a shirt or a dress, we all have a button down in our closet. I love button downs because they’re so versatile and easily styled, no matter the season. For the summer to fall transition whether it’s a shirt or a dress, keep things simple and grab a light layer to wear over top, and pair it with the shoe you’re most excited to pull out for fall – I’ll be grabbing my favorite booties.

If your button down is a shirt, pair it with jeans or a cute fall slack – remember, wider pants are in right now, so pull yourself away from your skinny jeans and go for a looser fit.

Summer To Fall Transition Outfit
Transition Outfit Fall

WE LOVE Long Sleeve Dresses

Dresses are one of my favorite things to wear because you know that you’ll look put together, but you really don’t have to think that much through when styling the outfit. Long sleeved dresses are perfect for the fall transition outfits because they’re warm enough to keep most of the chill off without needing a ton of external layers. You can just pair your favorite dress with a great pair of boots – tall or ankle – grab a shoulder bag, and be ready to go!

The further you get into the season, the more you’ll find yourself reaching for another layer to keep with you, just in case – for the evenings, I love a trench coat. After all, a trench coat and boots? What could be more stylish?



Business casual looks are some of my favorite fall transition outfits to style. I like to keep my summer tank tops out for this very reason – a well-made, stylish tank layers perfectly underneath a blazer for a look that keeps you cool without being too chilly. Plus, fall is the prime time to shop for great pants for the office, as stylish trousers are everywhere. The wide leg look is still super popular this year, so now is the time to invest in some great pieces to keep you looking chic every time you head in to the office.



When it comes down to it, the key to the perfect transitional outfits is simple – layers are your friend. Whether it’s a skirt and tights, a dress and a leather jacket, or a cardigan over a tank, layering is the best way to bring your summer items into the first weeks of fall amidst the transitional weather. 

Oftentimes, the best looks are the most basic. I like to build on my favorite summer tank top by pairing it with a great pair of jeans, layering a sweater overtop, and adding some summer sandals as a final touch. Accessorizing with a neutral toned bag is a great way to bring the look into the fall season as well.

Fall Transition Outfit Lulus


The transition from summer to fall doesn’t have to be daunting. It’s far easier than you might think to transition your wardrobe to the cooler weather, and the time in between seasons should be a fun experimentation, not stressful! Here are some of my top tips for easy ways to make the switch seamless.


You already know that layers are the way to go when trying to put together the perfect fall transition outfit, but don’t feel like you just have to throw a sweater on every morning. Experiment and play – remember, some of the in between days are warm enough that you might not even want to wear a top layer all day. Try wrapping a layer around your waist, or tying it around your shoulders. You won’t know what you like unless you try!


The colors that you wear completely set the tone for the feel of your outfit. If you want to emphasize the fact that you’re transitioning your clothing to fall, make sure that the colors you’re wearing reflect that. Fall is the season of earth tones, of deep greens and browns and burnt oranges. Incorporate burgundy or great neutrals that really make you feel like autumn is here. And while you may be hesitant to go for darker colors while the weather is still warm – I know, darker colors can be brutal in heat and humidity – if you specifically aim for breathable fabrics, you’ll stay cool while still looking autumnal.


Let’s be honest – in some places, the early months of fall don’t feel much different temperature-wise than the summer months. If you find yourself still stifled by the heat and can’t bear the thought of adding a layer to your look, pull out the autumnal accessories instead. Great neutral or earth-toned bags are a perfect touch to any look, and you can begin to transition your makeup to the autumnal color palette before you start pulling on the sweaters. You can even wear fun fall hair scarves that give you that seasonal touch while also subtly keeping your hair off your neck in the heat – a win-win!


The easiest way to slowly begin bringing fall into your wardrobe is to wear more denim. A great pair of jeans or a denim jacket can pair perfectly with any of your favorite summer pieces as a gentle way to head into the new season.


Even if you aren’t ready to make the jump to boots yet, simply switching your sandals for a closed-toe shoe is a great first step to heading into the fall season. And with so many adorable flats on the market right now, who can complain about that?

Lulus Fall Transition Outfit 1
Lulus Fall Transition Outfit


Still not sure where to begin? Here are a few of my favorite pieces for the summer to fall transition.

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