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31 Transitional Fall Outfits For September To Add To Your Must-Try List This Month


It's not official just yet, but summer is over. But here's a little good news: The pieces you've been wearing on repeat the last few months don't have to meet their impending end just yet. If you strategically cherry-pick a few transitional fall outfits for September, you'll be able to weave those breezy, beach-worthy styles into your not-so-distant future. The key is nailing the September high-low style trick: For every hot-day piece you put on, pair with one that's better suited to low temps.

A tank dress can make it into fall if you add a turtleneck underneath. If you still want to wear sandals and a slip dress, better be sure to add a blazer and tights. And while trends like bright green hues and pearl jewelry aren't going anywhere, they require the balance of a tailored tweed jacket or structured shoulder bag to fit the upcoming season's more serious feel. Below, you'll find 31 fresh outfit ideas to help you navigate the month ahead. You've outgrown the excitement of going back to school, but that doesn't mean you have to give up the joy of learning something new. Plenty of creative ideas to absorb below, and luckily there's no need to cram.

Endless Summer

Transition your summer staples — like sporty sandals — by starting to style them with new season pieces.

Seasonal Stripes

Though you're not obligated to embrace rich fall hues — bold colors are trending after all — a multi-hued print is an easy way to get into the seasonal swing of things.

Fresh Leather

Incorporate unexpected leather (or faux) pieces into your ensemble to transition your look. A short sleeve shirt works solo, or can be layered with a turtleneck underneath.

Dressed Up Denim

Take the fuss out of fall tailoring by styling a blazer with relaxed high-waist jeans.

Mix And Match

Break out the turtleneck early and style it with staples usually reserved for warmer temps — like flip flops and bermuda shorts.

Swim Styling

Don't abandon your swimsuits just yet. Breathe new life into your beach staples by transforming your favorites into tops.

All About Texture

Begin to play with texture by swapping in one or two pieces of clothing that are a bit heavier than your summer wares. A soft coat or slick pair of pants will do the trick.

One And Done

Don't underestimate the power of a great jumpsuit. This simple piece makes getting dressed for work a total breeze.

Embrace The Trench

Classic trench coats are back in action, so find the one hanging in the back of your closet and bring it out anew.

Tights Trend

While printed tights and bold colors are both editorial-inspired options for fall, you can't go wrong with classic black. Style with your transitional dresses and a pair of cool boots.

Classic Cool

Extend the life on your denim cutoffs by styling them with more fall-worthy staples like a blazer and cowboy boots.

Soft And Hard

Add some edge to your light florals by styling with slick patent and chunky black footwear.

All About Neutrals

Neutrals don't have to be boring. Layer slightly-varied colors all together at once for an outfit that has intrigue, but is still on the subdued side.

Balanced Romance

Style your favorite puff-sleeve top with sporty sneakers and relaxed light-wash denim for an outfit that's sweet but not overly so.

All Over White

Ignore the outdated rules about white after labor day and transition to fall with wide-leg pants and a cardigan.

Comfortably Chic

Biker shorts and a blazer are an unexpected combination that looks more polished than you might first assume.

Sheer Details

A sheer top layered underneath your favorite dress or summer tank is a great way to get a jump on transitional dressing.

Scarf Styling

Even if you're not ready to break out a heavy cashmere number yet, you can begin to get creative with your scarf styling.

Chunky Chains

Chunky necklaces are an easy pick if you're searching for jewelry that will pop against higher necklaces and thick knits.

Plaids Please

Shorts, sneakers, and a plaid top or sweater — it's a simple combination that feels just right for September.

Dress And Sneakers

Take a break from boots and style a sporty sneaker with a polished dress.

Keep It Simple

Like the aforementioned trench coat, a simple and sleek khaki skirt is an easy fall staple to help transition your look.

Not-Your-Average Tweed

Put a twist on classic tweeds by swapping in something bright and unexpected.

Shoes First

If you don't want to worry about all the fall layering, you just need to remember this simple rule. Start with a pair of statement shoes and pick a few simple pieces you can wear with them.

Mixed Prints

Don't be afraid to mix and match contrasting prints together. Try staying within the same color story and varying print sizes to keep things simple.

Pop Of Color

If your usual style is a bit more subdued, style your usual navy, black, and neutral pieces with a pop of bold orange or pistachio.

Simple Perfection

To add intrigue to an all-black ensemble, play with texture by mixing in velvet, tweed, or cashmere.

Animal Alternatives

Though leopard, tiger, and zebra prints aren't going away entirely, consider a fresher take on these trends by finding looks in new colors, or with patterns that are a little less on the nose.

Add A Cardigan

Ease your way into sweater season with an easy cardigan you can throw on over a tank.

All Over Denim

Mix and match denim hues for a fresh take on teh canadian tuxedo.