5 Dressy Casual Fall Looks

Dressy Casual Outfits for Fall
Keeping with the series of 5 Go-To Outfits at varying levels of casual to dressy, today I’m showing 5 Dressy Casual Fall Looks.  We started with five outfits you could wear for weekend or errands.  We followed with five outfits that I call “put together casual” which are outfits that are still casual but a step up from the weekend looks and things I’d wear when hanging out with adults (i.e. not doing tons of movement like wrangling kids and hours of errands).  Today’s looks are “dressy casual.”  They’re far from semi-formal and still mostly involve jeans, but they’re sharper than outfits in the previous posts.
SIZING INFO: I’m 5’6″ and usually S/M or 6/8 in clothes, 8.5 to 9 in shoes.  All sizing details for pieces are in “Shop the Look” sections below.
Maroon Swing Dress + Plaid Blanket Scarf + Booties + Tote
Plaid Blanket Scarf + Tan Booties + Maroon Swing Dress + Brown Bag + Jord Watch
Maroon Swing Dress + Tan booties + Brown Tote + Plaid Blanket Scarf + Jord Watch
First is a comfy casual dress that is dressed up a little with a scarf and booties.  If it’s too hot for a scarf, wear a statement necklace instead and you’ll have the perfect mix of dressy casual.
My maroon dress is from last year and is back again HERE.  Please note these dresses tend to run short, so try ordering Tall sizes if you’d like more length.  I found a very similar second option that is only $14.99, is longer at 38″ inches, and has pockets!  See it HERE in tons of colors.
This scarf is a favorite from past seasons and can be found in a lot of places.  There’s one for $13.99 HERE!
Shop for the Look:
Dress: Old Navy (exactalmost exact–longer with pockets)
Scarf: c/o ModCloth (almost exact)
Booties: Nordstrom (exact–wearing 8.5) 
Watch: c/o JORD (exact)
Bag: c/o Lily Jade (exact
black swing dress + leopard scarf + tan booties
black swing dress + leopard scarf + tan booties
black swing dress + leopard scarf + brown booties + cognac bag
This is the same outfit formula with the exact same dress in another color.  It’s definitely a go-to formula and works like a charm!
Shop for the Look:
Dress: Old Navy (exactalmost exact–longer with pockets)
Scarf: Nordstrom (exact–only $19)
Booties: c/o Sole Society (similar–only $32 with good reviews)
Bag: Nordstrom (exact)
Watch: c/o JORD (exact)
Tan Cardigan + White Blouse + Black Skinnies + Leopard Flats + Gold Earrings
White Blouse + Tan Cardigan + Black Skinnies + Gold Earrings + Gold Necklace + Leopard Flats
Tan Cardigan + White Blouse + Purse + Black Skinnies + JORD Watch + Gold Necklace + Leopard Flats
I often wear jeans with a cotton tee and a cardigan, but with a few tweaks you can sharpen up that combo.  Wear a non-cotton blouse instead, and add pointy toe flats to combat the droopiness of the cardigan and blouse.  Finish it off with jewelry!
Shop for the Look:
Top: Nordstrom (exact–wearing M)
Cardigan: Old Navy (exact in other colors; similar)
Jeans: Nordstrom (exact–wearing size 6)
Necklace: c/o Dear Mushka (exact)
Watch: c/o JORD (exact)
Shoes: Nordstrom (similar)
Bag: Nordstrom (similar)
Earrings: c/o Nickel & Suede (exact)
Black Blouse + Bootcut Jeans + Leopard Heels + Black Bag + Gold Necklace
Bootcut Jeans + Black Blouse + Gold Necklace + Black Sunnies + Leopard Heels
This is a similar idea to the outfit above, with almost the exact same top except it’s the shorter version in a different color.  Instead of skinny jeans I went with bootcut jeans and a low pointy toe heel.  I love the difference bootcut jeans and heels can make in stepping up an outfit!
Shop for the Look:
Top: Nordstrom (almost exact, almost exact but long version)
Jeans: Nordstrom (exact–wearing size 8)
Shoes: Sole Society (similar, similar
Bag: c/o Sole Society (similar)
Necklace: c/o Dear Mushka (exact)
Watch: c/o JORD (exact)
Sunglasses: Urban Outfitters (exact)
orange floral print dress + navy cardigan + tan suede boots
orange floral print dress + navy cardigan + tan suede boots + leather accessories
orange floral print dress + tan suede boots + navy cardigan + tan accessories
Another dress look here, but compared to the pajama swing dresses in the first set of outfits, given this dress’ material, it could be dressed up more.  To dress it down I paired it with an oversized cardigan, but you could also use a denim jacket.  Finish it off with suede boots!  And BTW, I got my suede boots last year but they are still in stock on Amazon in my exact color HERE and a very similar color HERE.  They run narrow, IMO.
Shop for the Look:
Dress: c/o ModCloth (exact–wearing size M)
Cardigan: H&M (super similar)
Boots: Lucky Brand (exact, exact in similar color)–I wear 9.5
Belt: H&M (super similar)
Bag: Nordstrom (similarsimilar)
Watch: c/o Daniel Wellington (exact)
Earrings: c/o Nickel & Suede  (exact)
Red Orange Lace Top + Dark Skinnies + Nude Pumps + Tan Clutch + Statement Necklace
Red Orange Lace Top + Tan Clutch + JORD Watch + Statement Necklace + Skinnies + Nude Pumps
I recently showed this outfit, but I just love it so much!  A lace top (of any color), jeans, heels, and a statement necklace is one of my go-to dressy casual outfits.  It’s so easy and works every single time!
Shop for the Look:
Top: ModCloth (exact–wearing M)
Jeans: Nordstrom (exact–wearing 4)
Shoes: Target (updated version)
Necklace: Nordstrom (almost exact in rose gold)
Clutch: DSW (similar)
Watch: c/o JORD (exact)
Some of these might work for a meeting where you need to look more put together, and some of them may work for a daytime party or girl’s gathering.  Try one for your next dressy casual event!
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  • Reply
    Savvy Southern Chic
    November 2, 2017 at 1:38 pm

    You have such a great effortless style!

  • Reply
    November 2, 2017 at 5:08 pm

    I’m so excited you showed outfits that did not feature skinny jeans! I love the bootcut jeans outfit and the dresses. Great post!

  • Reply
    November 2, 2017 at 9:07 pm

    Love, love, love your outfits! Sorry if it is a silly question but what kind of socks do you wear when you were your booties?

    • Reply
      Lindsay Sutherland
      November 3, 2017 at 4:18 am

      I don’t know about Audrey, but I don’t wear sock with my booties 🙂

      • Reply
        November 3, 2017 at 7:42 am

        Thank you for sharing!

  • Reply
    Lindsay Sutherland
    November 3, 2017 at 4:19 am

    Love the dress in the two different colors! Same outfit formula but when you mentioned that it was the same dress but a different color I was like oh really? And I had to go back and look at the first dress outfit because I thought these were two completely different dresses lol! Good job!
    Question about the dress shown in two different colors. How does it wash? Did you have any issue with shrinking? Also, did you buy the “tall” size?

  • Reply
    November 3, 2017 at 3:54 pm

    Love that orange dress so much, it’s perfect with the navy cardigan! 🙂

    I like how these outfits have just a little something special to make them a little dressier – I need to get better at doing that with my outfits, I wear casual clothes most of the time!

    Hope you are having a lovely weekend 🙂

    Away From The Blue Blog

  • Reply
    November 3, 2017 at 6:42 pm

    I’m so excited to see a post featuring non-skinny jean outfits! I love the dresses and the bootcut pants outfit. Great post!

  • Reply
    The Gluten Free Guide to Everything
    November 4, 2017 at 2:49 am

    Very cute and stylish looks, I especially like the one with the lace top!

    Marije | thegfguide.com

  • Reply
    November 5, 2017 at 8:46 am

    Love, love, love your outfits! Just curious, when you wear booties, what kind of socks do you wear?

  • Reply
    Natmari's Corner
    November 6, 2017 at 12:00 pm

    The first outfit is so beautiful! You hit the nail on the head when it comes to dressy casual fall outfits. 🙂 You gave me some great ideas.

  • Reply
    Mandi Patel
    November 9, 2017 at 4:53 am

    Hi! I love your style and have basically outsourced the getting dressed part of my brain to you!😜 The only problem I’m having now is that I live in Michigan and it’s REALLY freaking cold here! I have almost everything in your fall capsule, but I’m having trouble staying warm! Could you please do a post on being warm, cute, and simple?!

  • Reply
    December 3, 2017 at 4:19 am

    I loved your bags in all the 6 outfits and the boots. I am a fan of sling bags, what type of outfits do they go with? Are the always used only in casuals?

    • Reply
      Audrey @ Putting Me Together
      December 3, 2017 at 2:42 pm

      Hi Ramya! I’ve only really seen them used in casual outfits, though maybe a really sleek leather one could work in a dressier look? Not sure though, sorry!

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