If summer is for showing off how great you look without a lot of clothing, fall is for demonstrating what you can do with your wardrobe. It's time to burrow into your oversize fuzzy sweaters and wear the same pair of blue jeans Monday-Friday. (But every outfit will look different—we promise!) Fall fashion means figuring out how to layer without looking like an overstuffed penguin and revisiting your favorite transitional-weather gear, from chunky ankle boots to classic trench coats. We're going to show you how to easily recreate 20 cute autumn outfits, as seen on the streets. Read ahead for some quick styling tips and shop similar pieces to get started on your fall looks.
In the summer, sleeveless dresses and tops are your go-to for beating the heat and getting sun-kissed shoulders. Come fall, though, maxi dresses with sleeves will be your BFF because they'll provide coverage once the temperature dips. You can style your maxi or midi with a denim jacket and a pair of boots.
Shop similar: Tory Burch midi dress, $478
There is a small weather window for when you can wear your summer clothes with fall pieces, like a good 'ol bootie, without your outfit looking weather-confused. Take a tip from Aimee Song and go for that head-to-toe black look, her floral booties add a cute touch. Or, try a bright summer dress with a moodier pair of booties.
In the early days of fall, all you need is a blazer to keep warm in the early mornings and after sunset. Find one that will match with your Monday through Sunday outfits or do the opposite and invest in that one statement piece. Either way, blazers works well with all your transitional weather pieces, from a pair of jeans to skirts.
Shop similar: Industrie Africa blazer, $575
Start embracing your winter whites as soon as the air feels crisp and a chill sets in. To break up the neutral look just a tad, insert a print. Camille Charriere went for the classic polka dot, which tied in nicely with her snow white sweater and booties but still stood out as the main attraction in her outfit.
When you have on a statement coat, you can wear sweats underneath and no one will bat an eye. Now's the time to show off your favorite glossy trenches and teddy bear-inspired shearling jackets. A good fall coat is one investment piece you shouldn't skimp out on.
Shop similar: Ainea vinyl trench coat, $178
Autumn's cooler temps mean you can finally break out your new leather pieces. Buttery soft leather will always be in, whether it's a shirt, dress, or even jumpsuit. Nanushka is one of the brands that does this best, so investing in a piece from the label is a must.
Shop similar: Nanushka faux leather shorts, $391
Instead of buying another pair of black skinnies, think outside of the box and choose a deconstructed pair. The crisscross button design is wearable and not a dramatic change to your wardrobe (for those who are more trend-wary), yet it still adds a level of coolness to your sweater or t-shirt.
Shop similar: Agolde crisscross jeans, $218
Give your beloved button-down shirt new life on the weekend with a shimmery skirt, like this sequin number. You'll look instantly dressy for whatever going-out plans you have. If your office dress code is more lax, you might even be able to get away with this look come Monday morning.
Shop similar: House of Harlow 1960 skirt, $51
Fall officially signals the start of denim jacket weather. (Even if you've been wearing yours around the office because #airconditioning.) To breathe new life into your look, incorporate a shimmery, metallic top. Street style star Andresha Debourg went the extra mile with two different colored shiny pieces for a fancy-but-dressed-down vibe. Tie your ensemble together with a pair of sneakers that match your top.
Shop similar: Mother denim jacket, $211
One way to dress for tricky transitional weather is with layers. To wear your summer pieces—like a linen jumpsuit—into the fall, slip a thin turtleneck sweater underneath. Weather-permitting, you can skip the jacket altogether.
Shop similar: H&M ribbed turtleneck, $15
If summertime colors are all pinks and yellows, then fall calls for muted tones like burnt orange and rich burgundy. You'll soon find that brown and orange hues are just as versatile as black or navy. Don't be afraid to mix and match various prints in these shades, like the ladies on the left.
Shop similar: Wales Bonner knit shirt, $278
A foolproof way to make your summer slips fall appropriate is with a lightweight cardigan. The cover-up gives offers that extra warmth, necessary since spaghetti straps don't exactly provide you with much coverage. I recommend having a taupe or beige option that will go with everything in your closet.
Shop similar: Fendi cardigan, $1,690
Not ready to trade in your lace-up sandals for suede ankle boots yet? I feel ya. Luckily, in the early weeks of autumn, you can still wear open-toe sandals or woven espadrilles without flirting with hypothermia. Style your summer shoes with your favorite long-sleeved T-shirt dress or a cozy fall sweater and jeans.
Shop similar: Banana Republic t-shirt dress, $33
Here's an idea for a fresh way to style your most-used piece of outerwear: Leave it unbuttoned, wear it slightly off one shoulder, then roll up your jacket sleeves to expose the sleeves of your shirt. To keep the coat on, simply belt it. This slightly disheveled, but effortless fashun look will make everyone on the streets do a double take—in a good way. Plus, now your cute top won't be hidden under your trench coat.
Shop similar: Seventy Venezia trench coat, $208
My favorite fall combination is a dress over jeans because I'm not a fan of tights (sorry, Kate Middleton). They always rip! This simple combination ensures you can wear your Free People summer dress and your fall jeans without picking favorites. When it comes to what kind of denim you should wear underneath, go for a straight or slim fit with a cropped or frayed hem for extra style points.
Shop similar: Levi's jeans, $119
Plaids are always in for fall/winter. An unconventional way to work this classic print into your outfit is with an accessory, like this Les Petits Joueurs handbag. Caroline Daur added some color to her all-black ensemble by toting around a plaid bag and topping it all off with blue sunglasses and a red lip.
Shop similar: Pamela Munson bag, $185
Find a good pantsuit set and you're good to go for any work event or fancy dinner party. The two-piece look is so easy to wear (I like to layer a crop top or tee underneath) and you can rock it with sneakers, mule pumps, boots, or flats. Best of all, you can wear the coordinates separately or together, like this Fashion Week attendee did.
The cool, but not muggy, temperatures in the fall make it possible to wear things like a sweater dress and not suffer a heatstroke. Instead of accessorizing with a belt, strap on a waist bag to highlight your midsection and to break up the look. While this fashionista chose a pair of sparkly boots, you can trade in booties for sneakers or a cool Everlane glove heel.
Shop similar: Free People sweater dress, $99
The shearling jacket is a good in-between option for days when you can't wear a leather jacket (it's too cold), but you also don't want to wear a down coat (it's not really winter yet). Two years ago, I found the best one at Forever 21, which I wear over and over with jeans and boots—simple. The jacket shields me from the wind and keeps me warm, though I don't recommend wearing it in snow storms: the shearling gets wet and crusts over.
Shop similar: AllSaints biker jacket, $770
Pause! Don't pack away your summer skirts yet. You can rework them for fall in several easy steps: 1. Find a sweater thin enough to tuck into your skirt, 2. Wear a pair of tights underneath your skirt, 3. Style with the ankle or knee-high boots of your choice. Top with your favorite transitional jacket and, voilà! Your skirt is now ready for #OOTD photos at the pumpkin patch.