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Choosing Your Outfits for Fall Photos (Chicago Edition)

Monday, September 15, 2025 | By: Scarlett Photography

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Choosing Your Outfits for Fall Photos (Chicago Edition)

Quick Take 

  • Start with neutrals (cream, camel, oatmeal, taupe, espresso, navy) then add one or two autumn accents (rust, burgundy, forest, sage, ochre).

  • Coordinate—don’t match. Build around one “hero” outfit and layer supporting textures.

  • Prioritize fit, movement, and texture over busy patterns.

  • Expect Chicago weather swings; plan light layers and closed‑toe shoes.

  • Keep accessories minimal; think elegant, not fussy.

Textured Blazers in timeless colors 

QUICK SEARCH for textured blazers ready to ship fast!

 

GET THIS ONE!

 

 

Alakuoti Girls Fall Long Sleeve Dress Floral Ruffle Flower Girl Formal Party Holiday Midi Dresses with Belt 5-14 Years

ORDERED THIS FOR MY 6 YEAR OLD!

 

 

Check out more girl's fall dresses

 

STOP IT!  I just found this for on sale!!!  And how perfect will this denim jacket be layered over this dress! 

 

The Children's Place Baby Toddler Girls Basic Denim Jacket

Denim Jacket

 

Kid Toddler Girl Fall Dress+Cardigan 2 Piece Floral/Plaid Sleeveless Dress and Cardigan Set 2-14Y

Love this too!  2-14Y, but I would pair this with the denim jacket above.

Dress with cardigan

 

Women's Suede Belt

LOVING Suede this fall and I need to get this belt!  

Women's Suede Belt

Check out these fall outfits below!

Here are some great fall colored dresses for moms.

  

Green Flowy Dress        Burnt Orange Dress

These are affiliate links, which means if you purchase any of these items, I get a small commission.

 

 

 

For something a little more fitted.  This sweater, dress is beautiful and still allows for fun movement throughout your session.  It has great reviews too! 

Cream Sweater Dress

 

CLICK HERE TO SEE FITTED FALL DRESSES FOR MOMS

 

 

Lucky Brand Women's Baley Ankle BootAmazon Essentials Women's Lace-Up Combat Boots

 

FALL BOOTS! MY FAVORITE!

 

Personally, I plan to wear high-waisted medium/dark wash denim, with a lighter sweater like this - I plan to size down since it's a more comfy fit -  so it's short enough to do a light tuck into the high waisted denim and so it's not frumpy for photos.

 

 

Comfy, light sweaters

 

I am not an affiliate for Rag & Bone, but my favorite denim are these!  I am not one who thinks all denim is created equal and this is one closet staple I will splurge on.  But I also think it's hard to find good denim online - you really need to be able to try it on!  But I am a little curvy and these compliment me so well and our comfortable.  They don't stretch out much as you wear them and the color is timeless.  The length is PERFECT for me at around 5'7.

Flexi Sofie Wide-Leg Jean image number 3

https://www.rag-bone.com/p/flexi-sofie-wide-leg-jean-WDD24F2952FUWI.html

 

Keep reading for even more advice on making sure your entire family looks fantastic for your fall photos.

The 2025 Fall Outfit Palette: Elevated Neutrals + Layered Autumn Tones

 

Neutral foundations let faces and connections take center stage. Add color depth with one or two seasonal hues.

Foundations (neutrals): cream, ivory, oatmeal, camel, taupe, greige, navy, charcoal.

Accents (autumn): rust, copper, terracotta, cinnamon, burgundy/merlot, forest, sage, mustard, steel blue.

 

What Not to Wear 

  • Loud logos, neon, or tiny high‑contrast stripes (can “strobe” on camera)

  • Ill‑fitting, too‑tight, or too‑baggy clothing

  • Oversized smartwatch bands or bulky keys/phones in pockets

 

 


 

Coordinate, Don’t Match

  1. Choose one hero outfit (often a dress or knit in a textured neutral).

  2. Pull 2–3 complementary colors from that piece.

  3. Build supporting looks using solids + textures (knit, rib, corduroy, linen blend, suede).

  4. Repeat colors sparingly across the group to create cohesion.

Avoid identical outfits or everyone in plaid—visual rhythm > uniformity.

 

 


 

Fabrics & Texture That Read as “Quiet Luxury”

  • Knit sweaters, cable cardigans, ribbed tops

  • Flowy woven dresses/skirts (midi length photographs best)

  • Corduroy, wool, twill

  • Suede/leather accents (belts, boots)

  • Dark-rinse denim 

 


 

Prints & Patterns (Use with Intention)

  • Keep prints small to medium scale and low contrast (ditzy florals, micro-check).

  • Try to limit to one pattern per mini-group; anchor the rest in solids.

  • Avoid logos, cartoon graphics, and neon.  These are not timeless, and for timeless photos, neon is always a no.  

 


 

Fit & Silhouette - Where what looks AND feels good!

  • Choose shapes that allow movement and natural interaction: midi dresses, A-line skirts, soft trousers, straight or tapered denim.

  • Tailoring matters: steamed/pressed pieces look instantly elevated.

 

 


 

Weather‑Wise Layering (Chicago, Late Sept–Nov)

  • Base layer (thin thermal or slip), then knit, then light jacket/coat.

  • Bring neutral outerwear you’re happy to see in photos (wool coat, quilted jacket, trench).  Being super cold is not going to help your child have a good time!

  • Closed‑toe shoes or boots; socks should match pants/shoes.  Feel free to add some personality and fun with these!  But keep it in the same color family as the rest of your wardrobe.

Rain plan? I keep a flexible approach—overcast can be gorgeous. If needed, we’ll choose a covered spot or reschedule according to your contract.

 


 

Shoes & Accessories

  • Boots, loafers, appropriate sneakers, flats, sometimes heels will work but be mindful of your chosen location.  Pro-tip: If you insist on wearing your fave heels, bring slides for most of the walking and you can swap when photographing.

  • Belts, dainty jewelry, hair bows/clips in soft/complimentary tones.

  • Hats (use caution) and scarves are great layering props—we’ll add/remove for variety.

 

 


 

Hair, Makeup & Grooming

  • Skin: natural finish with light powder to reduce shine.

  • Cheeks/lips: wear whatever color you would typically wear- don't try anything new on session day; lip balm for all ages.

  • Nails: clean neutrals are best, but again, whatever you typically do is great.  No chipped polish.  

  • Do your best to keep clothes wrinkle-free.  You can always add your top layers when you arrive to the photoshoot location.  I would suggest putting the final layer on kiddos when you arrive if you plan to give them any kind of food/drink in between dressing and photos. 

  • make sure dad trims those wild nose hairs and cleans up hair/facial hair line before your shoot.  

 


 

Kids & Babies

  • Comfort first—soft layers (knit tights, ribbed leggings).

  • Avoid stiff collars and scratchy seams.

  • Neutral pacifiers/blankets if they might appear.

  • Bring a simple backup outfit just in case!  

 

 


 

Make What You Already Own Work

 

  • Pull 3–4 pieces you love. Build the family palette around them.

  • Swap buttons/belts to elevate basics.

  • Layer a cardigan or trench over a simple dress to add dimension.

  • Monochrome trick: vary texture within one color family for a polished look.

 

Day‑Of Checklist

  • Steam outfits; pack a small kit (lint roller, powder, wipes, hair brush, tissues) If you are photographing with me, I bring a lint roller, wipes, and tissues!).

  • Bring water/snacks that won’t stain clothes or mouths.

  • Remove watches/fitness bands unless you want them in the photos.  

  • Empty pockets (including phones!).

  • GPS the meeting location the night before*

 


FAQs

What colors look best with fall leaves?
Neutrals layered with one or two soft autumn accents (rust, sage, burgundy) photograph beautifully without competing with the foliage.

Can we include our dog?
Yes! Bring a neutral leash/collar and if your dog has long hair - make sure you have them groomed so we can see their eyes.  BRING TREATS and a squeaky toy if you think it will help.  

What if it rains or is windy?
Overcast is flattering. For heavier weather, we’ll pivot to a covered location or reschedule per your contract.

Do you help with styling?
Absolutely. Send outfit photos; I’ll suggest tweaks and finalize a palette.

 


Book Your Fall Session

Petite Fall Sessions (limited, Riverside and Waterfall Glen) and Signature Outdoor Sessions are now open. Availability is intentionally limited to keep the experience calm and personal and keep me from burnout - Holiday/Christmas photos are right around the corner.


→ View Fall Photo Options - Pricing & Availability HERE

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