Easy Transition Outfits: From Summer To Fall In 2020

Switching up your style game for each season can be complicated, and the transition outfits from summer to fall might be the most complex. In fact, we think putting away your summer looks and converting your everyday outfits from lightweight summer styles to heavier autumn pieces might be one of the biggest fashion challenges we all face.

This goes doubly so if summer seems to be dragging on forever when you’re craving cooler temperatures, apple cider, and colorful leaves. That said, you can easily get yourself out of the dog days of summer – style-wise, at least – by switching things up while still putting together looks that are appropriate for your current climate and weather.

Transition Outfits from Summer to Fall Tips

While we all probably aren’t going outside as often as we usually do this fall or dressing up as much as we normally do, it’s always fun to mark the changing of the seasons with some new ensembles. You don’t have to spend a lot to accomplish this goal, and you may be able to shop your closet as well.


* indicates required

Working on transitioning your wardrobe for fall? Here are some of our favorite ways to mix things up when we’re simply bored with our summer clothes.

transition outfits from summer to fall tops fountainof30
Madewell Texture & Thread Front Knot Jacquard Top, $39.50 and Anthropologie Natalie Cowl-Neck Cashmere Sweater, $168

Alter Your Color Palette

One of the simplest ways to make your outfits feel fresh for the new season is to switch out the color scheme; for instance, instead of wearing pastel blue, try something in marine blue or navy. Moreover, rust or burnt orange can be substituted for brighter citrus oranges (we love this side tie tee from Madewell and the Natalie cowl-neck sweater from Anthropologie), and deep purples and forest greens are definitely more autumnal than their pastel or bright counterparts.

Transition Outfits tips suede jacket fountainof30
Anthropologie Westley Sueded Jacket, $118

Play With Texture

Most summer pieces are lightweight and breezy, with either smooth and sleek textures (think silk or polished cotton or technical fabrics) or purposefully wrinkled like linen. On the other hand, fall clothes tend to have more variety and plushness, with textures like tweed, flannel, corduroy, suede, and velvet. One quick way to signal “autumn” with anything from a basic tee and jeans to a lightweight dress is tossing on a jacket. We particularly enjoy this drapey Westley suede jacket from Anthropologie. The rich olive shade is perfect for fall!

Transition Outfits summer to fall scarves fountainof30
Century Star Women’s Stylish Warm Tassels Soft Plaid Tartan Scarf, $10.99 | Century Star Century Star Women’s Fall Winter Scarf Classic, $9.99 | Inaini Pure Mulberry 100% Silk Square Scarves, $15.99

Swap Your Scarves

Adding a scarf or choosing a different one can update an entire outfit, even if everything else is the same. And if it is still too hot to think about wearing a scarf around your neck, consider tying a scarf on your handbag, using a scarf as a headband (pro tip – to keep a hair scarf in place, wrap it around a plain headband of your choice to keep things in place), or tying one around a ponytail or messy bun. These two Century Star scarfs in soft plaids or classics available via Amazon are ideal for layering, and this bold orange Ilnaini scarf (also from Amazon) would be great as a headband or hair tie.

Transition Outfits substantial handbag fountainof30
Botkier Highline Large Leather Tote, now $138.60 Reg. $198.00

Choose A More Substantial Handbag

Instead of lightweight straw or raffia totes or light-colored fabric bags, go for something more structured made of leather or vegan leather. We adore this rich burgundy tote from Botkier and it could easily change the tone of almost any outfit.

Transition Outfits summer to fall tights fountainof30
SPANX Women’s Tight-End Geometric Tights, $34

Add Some Tights

While a pastel maxi dress would be incongruous during pumpkin spice and apple cider season, some of your summer dresses and skirts – think solids and dark florals – can be worn well into fall by adding tights. Of course, basic black tights will always have a place in our hearts, but textured tights or patterned tights can be fun as well. These plaid Spanx tights can be paired with a variety of things and the black on black windowpane plaid pattern is very flattering.

Transition Outfits booties and slides fountainof30
Frye and Co. Jacy Chelsea, $83.40 and Steve Madden Forever Chain Pointed Toe Mule, $89.95

Change Up Your Footwear

Instead of strappy sandals, try some booties, mules, loafers or smoking shoes. These all can pair well good with midi dresses, shorts or crops, and any number of things. We’re big fans of these rich brown Frye & Co booties if you like chunkier styles, and these Steve Madden slides (particularly in the teal crocodile or the leopard print) for a more delicate look.

Shop Summer To Fall Transition Outfits

Do you change your color palette or style with the seasons beyond what is necessary to handle the weather and temps? How and when do you decide to make the shift? Let us know in the comments or in our Growing Younger Facebook group!


–Jacqueline Zenn

You may like to read more of Jacqueline’s fashion posts like How To Sell Your Clothes And Accessories Online and How To Decide If An Online Purchase Is Worth It.

This post contains affiliate links which may give us a commission at no additional cost to you.

Are you following Fountain Of 30 on Facebook, Twitter, Instagram and Pinterest? We’ve got lots going on, so join in on the fun! Subscribe to our newsletter here. You don’t want to miss a post and we promise not to bug you to death. We also started a Facebook Group called Growing Younger for women to discuss everything good and bad about being over 40. Be sure to listen to Lauren talk about all things anti-aging on the new podcast “Beauty is a Bitch!

Please pin!

fall 2020 transition outfits fountainof30

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.