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Fall· Fashion

3 Classic Fall Outfit Pairings

Thank you to Macy’s & ShopStyle for kindly sponsoring this post.
All opinions are 100% honest & all items were hand-selected by me.

Mango snake print crossbody

It’s so helpful to have a few go-to outfit combinations for each season that you can default to when you’re feeling uninspired or stuck in a style rut.  I’m all for playing around with trends, but when it comes down to it, at least 80% of your closet should consist of clothing staples – and these may be different for everyone, depending on your lifestyle, the phase of life you’re in & your personal style preferences.

Today I’m sharing 3 fall looks that I believe are always flattering & chic, while highlighting timeless wardrobe essentials that will last for years to come (and won’t be out of style by next year).  Right now, Macy’s is offering a whopping 30% off fall styles + 15% off beauty with code VIP through September 22nd!  This is one of their biggest sales of the season, so it’s a great time to grab those well-made investment pieces you want to add to your closet.

STRUCTURED BLAZER + DENIM

classic fall style

When it comes to fall layers, nothing adds instant polish to denim like a structured blazer.  When you choose a classic color & silhouette, this is a piece you’ll own forever.  The fit is obviously crucial with this type of tailored jacket, but length is equally important – while I love the look of an oversized boyfriend blazer, I think one that hits higher on the hip is the most versatile because it’s easier to pair with skirts & dresses without losing your shape.

This double-breasted blazer reminds me so much of the Veronica Beard styles that I’ve admired from afar – but the price point is so much better!  I found this to run true to size, but if you prefer a looser fit, I recommend sizing up one (especially if you have broader shoulders).  It also comes in a mustard hue & is available in plus sizing here!  Other options to try: this windowpane-print blazer, this classic black blazer, this plaid blazer & this tweed double-breasted jacket.  Here are a few more ways I’d style it for fall:

  • with this graphic tee, these cropped jeans & these sneakers
  • with this black square-neck bodysuit (bought & love!), this snake-print skirt & these booties
  • with this fitted top, this snake-print scarf, these skinny jeans & these over-the-knee boots
  • with this white blouse, these faux  leather pants & these pumps

Bar III Double-Breasted Blazer

Marc Fisher Croc Loafers

polished fall layers

olive buttoned blazer

What I’m wearing:
c/o Bar III Blazer, c/o Charter Club Sweater (similar for less here),
c/o Lucky Brand Jeans, c/o Marc Fisher Loafers, c/o Mango Snakeskin Bag

FLORAL DRESS + BOOTIES

INC Floral Wrap Dress

Sometimes you just need one pretty piece you can throw on & instantly feel pulled together – I firmly believe every woman should have at least one fall dress in her closet that makes her feel fabulous!  When you pick a style in a seasonally-appropriate color & pair it with booties, it’s a no-fail combination that can take you from desk to drinks to Sunday brunch.  I didn’t previously own any long-sleeved options, and I was constantly having to layer cardigans & jackets over my floral dresses for the colder weather.  So, when I came across this faux-wrap dress, I knew I’d found a winner.

The pretty print combined with the ruffle detailing gives it a decidedly feminine feel so I added a black belt, this croc bag and these pointed-toe booties to make it a bit more modern.  To give it even more edge, you could layer this moto jacket on top – and I think it would be easy to carry into the spring when paired with strappy sandals or white boots.  This dress is also nursing & bump-friendly because there’s an elastic waist + a hook-and-eye closure at the neckline.  I found this to run true to size, but if you’re unsure, I would size down one.  Other fall dresses I love include this floral maxi, this snake-print dress, this printed shift & this leopard print wrap dress.

ruffled floral dress

Carlos by Carlos Santana Booties

How to wear booties with dresses

wine floral print dress

INC Floral-Print Ruffle Dress

What I’m wearing:
c/o INC Floral Wrap Dress, c/o INC Belt, c/o Essentials Hoops,
c/o Carlos by Carlos Santana Booties, c/o INC Croc Bag

CHUNKY SWEATER + MIDI SKIRT

fall street style from Macy's

This might be my favorite combination of them all because it’s that perfect blend of comfy/chic + you can easily add tights and a wool coat when the weather gets colder.  The key to keeping a flattering silhouette with this pairing is either choosing a slightly cropped sweater or doing a front tuck so your waist is still defined. I purposely chose a midi skirt that wasn’t pleated or a-line to show you that this can work with many different styles (and because I love the smaller scale leopard print of this one!).

This mock-neck pullover is everything I want in a fall sweater – soft & warm, in a neutral knit with a slightly oversized fit.  I’ll wear this on the weekend with high-waisted jeans, a plaid scarf & leather boots.  If you prefer a slimmer silhouette, I’d swap out the chunky knit for this ribbed sweater (such a pretty color!).  Other midis worth checking out during the sale: this snake-print, this houndstooth print, this floral print & this leopard print.  See all of my top picks in the scrolling bar below!

1.State Ruffled Leopard Skirt

how to wear leopard this fall

1.State Leopard Print Ruffled Skirt

perfect fall outfit pairing

chunky sweater with midi skirt

What I’m wearing:
c/o Embossed Mock Neck Sweater, c/o 1.State Leopard-Print Skirt,
c/o Carlos by Carlos Santana Booties, c/o Mango Crossbody Bag

MY SALE PICKS

SHOES & BAGS

09.13.19 Kimberly

Related Posts

  • Layered Denim
  • Summer WorkWear
  • Cute & Comfy Looks for the Weekend
  • Making the Switch
« Steals Under $35
Cozy Fall Knitwear »
SALES ALERTS

Disclosure

Penny Pincher Fashion is a part of several affiliate networks. This means when you click on links to various merchants on this site and/or make a purchase, this may result in a commission that is credited to PPF. Also, as an Amazon Associate I earn from qualifying purchases. I take the responsibility of recommending products very seriously & will link to items that I personally love.

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