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This time of year is among the most challenging with regard to styling, in my opinion. The weather from late August to early October is unpredictable throughout most of the country, so there’s no way you can confidently pick a date and say, “that’s exactly when I’m going to start wearing my fall outfits.”

Enter transitional styling. Between-season summer to fall outfits are made possible by a small handful of “hero” pieces that either keep you cool while looking a little more autumnal or easily layer so that you can adjust quickly as the temperature changes. 

Below, my summer to fall transition essentials and outfit ideas for styling them now and later.

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Denim Jacket

This is truly a year-round staple, but I lean on it most heavily as my layer during early spring and early fall. Wear it over a maxi dress with booties in October or with chinos, a tee, and sandals in September. You truly can’t go wrong. I recommend a denim jacket with a slightly oversized fit, which is ideal for cooler temps so you can wear heavier layers underneath. This is the denim jacket I own; it’s a crowd favorite and fits true to size.

Long Dress

Having a one-and-done midi dress or maxi dress during the transition months can be really helpful. Even summery dresses are easy to create transitional outfits from. Fall-ify a summer dress with knee-high boots, booties, and sneakers. You can throw on a blazer or trench coat if it’s especially chilly that day. I love this sleeveless slip dress by Cuyana; you could wear it now with heels or flats and later over a turtleneck or underneath a cozy sweater.

Ankle Boots

When the temperatures are too mild for sandals and not cold enough for a full-on fall outfit, I’ll wear ankle boots with some of my summer pieces. I love neutral booties with denim cutoffs and a short sleeve tee, but they look just as great with white jeans, a silk cami, and a lightweight blazer. It’s also trendy to wear boots with dresses of any length right now.

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Outfit Details: MKT Studios Blazer (old, similar here and here), James Perse tee, Vince shorts, Veja sneakers, Rebecca Minkoff crossbody bag

Cardigan

Probably the number one rule of a transitional wardrobe is to incorporate layers. Cardigans come in all shapes, weights, and sizes, so whether you live in a cold climate and already need a chunky cardi or will be wearing lightweight cardigans until January, there’s something for everyone. I personally like lightweight cashmere styles that can be layered over (thin) knit sweaters and tees. Vince makes my all-time favorite cardigans, but they can be pricey. Here’s where I’d look for great cardigans on a budget.

Ankle Jeans

The perfect pair of transitional jeans needs to check a few boxes: versatile color, flattering fit, and easy to wear with a wide variety of shoes. Skinny jeans in an ankle-length cut will fit inside knee-high booties, show off ankle boots or heeled sandals, and work well with flats and sneakers. A few of my favorite brands for transitional denim are Madewell, FRAME, and Everlane.

Blazer

I didn’t start wearing blazers until several years ago, and I honestly have no idea why! Given that a blazer is made in a flattering cut, they are one of the most fall-appropriate layering items out there and SO versatile. I’ve seen them styled with a tank top or t-shirt, shorts, and slingbacks for late summer and love that look. Although, my favorite early fall fashion look with a blazer has to be with loafers, faux suede leggings, and a long sleeve blouse. I just ordered this under $50 plaid blazer from H&M.

Shop the Key Transitional Pieces

Summer to Fall Outfits

A few transitional summer to fall outfit combinations using the pieces above as a base layer to get your creative styling wheels turning.

• Slip dress + cable sweater + loafers
• Blazer + ankle jeans + sandals
• Cardigan + short sleeve tee + midi skirt + sneakers
• Long sleeve dress + ankle booties + hat
• Denim jacket + white jeans + blouse + mules

There you have it! These summer to fall outfits and pieces should make it easier to mix and match your summer wardrobe with your fall fashion favorites. While they didn’t make my top list of essentials, other great transitional items to include are a trench coat, leggings, a faux leather jacket, a button-up shirt, a jumpsuit, and a handbag in a fall color.

For more fall transition outfit ideas, make sure you’re following me on my social media channels: Pinterest (here’s my street style board), Instagram, and LIKEtoKNOW.it.