The 5 Pieces You Need to Transition Your Wardrobe to Fall (+3 Summer-to-Fall Transition Outfits)

Fall is almost here — are you ready?

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This post will show you the wardrobe essentials to take your style from summer to fall, plus cute fall transition outfits.

Though it might seem hard to believe, fall is just around the corner, making now the perfect time to think about how to tackle tricky transitional dressing. After all, we all know that uncomfortable feeling of being either over or underdressed on those in-between days when the weather is too hot for full-on fall outfits, but also too cold for summer ensembles.

So, that’s why today I put together three fashion-forward looks that are perfect for the last days of summer/the first days of fall.

{RELATED POST: How to Wear Your Summer Clothes in Winter}

Simply keep scrolling to learn the 5 must have items for the summer-to fall transition, plus fall transition outfits. Get ready to say goodbye to all of your summer-to-fall dressing woes!

Summer to Fall Fashion Essentials:

Item #1 – Midi-length Skirts & Dresses

I wear midi-length skirts and/or dresses all year round, but I especially love them this time of year.

Midi skirts and dresses are perfect for days when you know it will be both hot and cold. The length gives you enough coverage for mornings that are a bit chilly, but they are breathable and are not too heavy when it gets hotter throughout the day.

If you are wearing a midi skirt or dress in the final-days-of-summer/early-days-of fall, thin and flowy fabrics are a safe bet. When you are getting closer to mid-fall and the weather settles down a bit, you can still wear your lighter pieces with tights or swap them out for thicker fabrics.

Item #2 – Lightweight Sweatshirts

Sweatshirts are a staple in my closet. They are the most versatile item I own, right up there with basic tees and jeans.

Lightweight sweatshirts are perfect for transitional weather. You can just put one on in the morning and then throw it in your bag or backpack when it gets hotter.

The best thing about these sweatshirts is that you just need one in a neutral color to wear with any outfit you want, but you can also have some in bright colors if that’s more your vibe and you want to cover a brighter tee or top. There are so many options.

Item #3 – High-Top Sneakers

Sneakers are my go-to shoe. High-top sneakers, however, are my absolute favorites.

High-tops combine the best parts of a sneaker (flexible and breathable) with the best parts of booties (ankle support and coverage). Also, if you are like me and hate it when you can see your non-cute socks, you can wear thicker or longer socks with them without the socks peeking over the shoe.

A pair of black or white sneakers is probably the best if you want to get the most bang for your buck. You will wear them a lot and they go with everything. Mostly, I reach for Converse (in various colors) but there are thousands of different high-top sneakers that fit everyone’s style and vibe.

Item #4 – Denim Jacket

Leather jackets are my favorite type of jacket. But the ones I wear the most are my denim jackets.

Denim tends to be the type of jacket you can throw on with anything, and it’s a total fall staple. Blue, black or white denim are your safest bets, but right now there are some really cool denim jackets in bright colors, pretty prints or even tie-dye if that’s more your speed.

Personally, I have jackets in blue, red, and black denim.

My favorite denim jacket cut is oversized, especially when the weather is crazy. I don’t like it when I wear one extra layer and I feel my movements are restricted because the jacket is too small.

Item #5 – Wide Leg Pants

Culottes, straight-fit and flare pants have come back in full force this summer. But my favorite type of pants for transitional weather is the wide leg pant.

Wide leg pants come in all shapes, sizes, fabrics, and lengths. They look super cute with crop tops, bandana tops and bodysuits, but also with sweaters, blazers and t-shirts.

Personally, I prefer my wide leg pants either in denim or in a pantsuit type of material. This is because I usually like to be able to dress them up or down with few changes, and with these types you can easily do it if you just change your shoes and makeup.

Also, the wideness of the leg, allows you to wear more types of shoes and higher socks if you get cold in the late fall.

3 Fall Transition Outfit Ideas

Outfit #1 – Summer Dress + Jacket

Fall transition outfit with white midi dress, black converse, black oversized denim jacket

The easiest transitional weather outfit combo is this one! A summer dress and a denim jacket go perfectly together this time of year. Both items allow you to battle the heat, but stay cozy in case the day gets chilly later on.

High top sneakers give this outfit a casual but modern look, but you can dress this look up anytime with booties.

Outfit #2 – Sweatshirt + Wide-leg Pants

An early class or job on campus can be tough to dress for this time of year. This is especially true for the start of fall, when you have no clue what the weather will look like on any given day.

Throwing a sweatshirt over a simple tank top or tee, and adding wide-leg jeans and a pair of sneakers will always be an easy solution and a pretty cute look. I love to reach for this type of outfit when I have no idea what to wear in the morning but want to look cute.

Outfit #3 – Midi Skirt + Sweatshirt + Jacket

Simple, yet put-together. This is the best way to describe the combination of midi skirt with a sweatshirt and a denim jacket. The different fabrics give the outfit some depth and will keep you cozy on the chilliest days this time of year.

What do you think of these fall transition outfits?

Do you have any items you want to recommend me for this type of weather? Which item would you wear? Would you use any of these outfits? Let us know in the comments below!

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