30 Days of Fall Outfits: How to Shop, Style and Mix-and-Match Your Fall Wardrobe

A good wardrobe is like a machine with interchangeable parts - everything should work together. Below, you can find 32 of my fall outfits as well as my tips on how to shop, style, and mix-and-match your way to amazing fall outfits.

The most challenging part of creating a wardrobe that you can easily mix and match is striking a balance between colorful, neutral, classic and statement pieces. I’ve been overhauling my fall wardrobe - assessing what I owned, shopping for a few new pieces, and figuring out how many outfit combinations I could create. My collection of clothes and accessories is small, but I was able to create over 30 different outfits! Read on to see what I learned.

My Fall Wardrobe
  • 4 long-sleeve t-shirts
  • 4 bags
  • 4 dresses
  • 4 flats
  • 3 sleeveless tops
  • 3 cardigans
  • 3 jeans
  • 3 boots
  • 2 button-downs
  • 2 jackets
  • 2 skirts
  • 2 heals
  • 2 belts
  • 1 cropped sweater
  • 1 leather jacket
  • 1 vest
  • 1 wool trousers
  • 1 pair of black tights
  • 1 scarf

My Everyday Uniform
Uniform

The best place to start is your everyday look. My default look is a pair of jeans, a basic top, boots and usually a jacket or cardigan. It can get pretty boring if all the items are neutrals. This year I focused on incorporating rich colors and prints into my “uniform” to help make my basic outfit feel more interesting. Here’s how you can do the same.

  • Determine your basic outfit: something that feels comfortable and fits your personal style. You most likely already have a tendency to wear a similar look regularly, so start there!
  • Choose a color palette that flatters you (mine is navy, marigold, tan, and burgundy).
  • Stick to one bright color at a time (unless you’re really good at pairing colors).
  • Try mixing a solid outer layer with a patterned layer underneath.
  • Make as many uniform looks as you can and save your outfit ideas inside Stylebook

Search through your closet for items you already own that fit your uniform and color palette. You probably already own a few things that fit your new formula.

STYLEBOOK TIP: Use Stylebook to create outfit collages of all the variations of your everyday uniform, so you can easily reference them when you're getting ready in the morning.

How to Clone an Outfit in Stylebook

Create and save variations of the same outfit with the Stylebook clone tool.

  1. Open the outfit and tap the clone button at the bottom
  2. An editable copy of the outfit will pop up. Tap plus to add items; double-tap and select delete to remove an item from the outfit.
  3. Tap Save when you're done.
Four Ways to Upgrade Your Everyday Outfit
Key Pieces

Everyone needs a few things in their wardrobe that can make any outfit better by adding a bit of personality and polish. Before you go shopping this fall, consider looking for a few standout items that you can wear frequently. Here are some of my suggestions for what to look for.

  • Texture: Seed stitch, cable knit and open-weave sweaters are just a few examples of texture. Leather jackets are also a good way to incorporate texture into a look. They give your outfit dimension and make an otherwise basic look stand out.
  • Shiny Details: Metallic details like a beaded collar accessorize your look without having to add any jewelry! Prevent them from looking too sweet by layering them with edgy items like a moto jacket or tough ankle boots.
  • Colorful Bag: This a really easy way to add a pop of color. Choose a color that compliments your skin tone and your wardrobe palette. Some good bag colors are emerald green, orange, pastel blue, plum and cobalt.
  • Layers: Interesting outerwear layers, like a vest, can help you get twice the mileage out of your outfits. Look for a fit you love in a neutral color so it can be worn frequently. Convertible pieces are always a plus!
My Key Pieces

These are my favorite items in my fall wardrobe:

  1. A classic satchel: I pull this bag out of my closet when I want to look more polished.
  2. Target T-shirts: The Merona Ultimate Tee is the best basic t-shirt. It fits well, comes in a lot of colors, miraculously never fades, and is cheap.
  3. Vest with detachable collar: Since the collar is removable, it's like having two different vests in one.
  4. Plum leather jacket: The leather texture instantly upgrades any outfit, and its knit panels make it as comfortable as a cardigan.
  5. Stylebook: I save all of my fall outfit ideas in Stylebook in advance. I have a great look ready for every day for the rest of the season.
  6. Colorful Bag: When my outfit seems too basic, I add this bag for a pop of color.

STYLEBOOK TIP: Search thousands of major stores with the shop feature in Stylebook. Find exactly what you're looking for by using the keyword search feature, as well as color, brand and price filters.

Shop for Special Items
  1. Open the shopping feature, enter a keyword like “textured” in the keyword box. Select a category like “sweaters”, choose a budget and tap search
  2. From the results grid, tap the item to see details
  3. Tap “Product Info” to get the price and open the product page on the store’s website
Fall Outfit Styling Tips
Monochromatic Outfits

I’m a strong believer in this look. Since I’m only 5’2” I need a little help to look taller and this always does the trick. Two other reasons to try this: It can really make your skin glow if choose a super flattering color AND it’s a no-fail way to mix prints or textures.

Here are three ways to pull off a monochromatic outfit:

  • One print item + one solid item in the same color
  • Two solid pieces in different shades of the same color
  • Two print items (with different-sized patterns) in the same color

Note: When wearing a head-to-toe monochrome look, it’s best to wear some neutral accessories

STYLEBOOK TIP: Search for specific colors of clothing while creating your outfits in Stylebook.

Create Outfits by Color
  1. Start a new outfit, tap the plus, and select the magnifying glass on the top left
  2. Choose your search criteria, like a color.
  3. All items that fit your search will appear in the bottom preview bar
Layers

I love knit dresses and layering is a great way to make sure I can wear them all fall and winter. One of the most versatile pieces in my closet is a T-shirt dress from Athleta, which is super soft and has waist definition, which I love!

In early fall/end of summer, you don’t need to wear any outer layers. A light jacket with a belt underneath works for days when it’s chilly in the morning but reaches summer temperatures in the afternoon. An oversized cardigan worn with with a belt on top for waist definition is ideal when it starts to get chilly. You could also add black tights to this outfit. When it’s freezing, wear a thin, long-sleeved t-shirt under the dress, a large cardigan over the dress, thick black tights, and a warm vest.

Styling

The proportions of an outfit and how your body is visually divided by the horizontal lines in your clothing are just as important as the clothing items that you choose. Below are some techniques to style well-proportioned looks that define your waist, elongate your legs, and narrow your hips.

  • Half-tuck: When you’re wearing a long vest or cardigan over a t-shirt, half-tuck your shirt. This will make the proportions of your outfit look more flattering since it brings the horizontal hem of your shirt above the widest part of your hips. If you feel like your outfit might look a little sloppy, try half-tucking your top and add a belt to see if it helps.
  • Waist Belts: Wearing a short jacket or sweater over a dress is a favorite combination for many but it can look a little shapeless. Wear a belt around your natural waist to redefine your shape. Try it both under and over your outer layer. I find it works better on top of sweaters or under jackets. Just make sure you don’t belt it too tightly!
  • Long + Short: Knit maxi dresses are comfortable, like wearing PJ’s outside of the house! After early fall has passed, you’ll need additional layers to stay warm. Don’t worry - it can be done! Whatever outer layer you choose, make sure it is short in length. Try cropped jackets, sweaters or even tank tops. This will draw the eye up and make your legs seem longer. This rule also applies to long vests and cardigans. If the outer layer is long, make sure the inner layer stops at your waistband. Wearing two long items at once has a tendency to look sloppy.
  • Crop Tops: Cropped tops are actually a lot more useful than they initially appear. Look for styles that hit just below the belly button and then wear them over a button-down shirt or a flowy silk tank. Let the bottom of the top underneath peek out below the bottom hem of the crop top. As with the maxi dress, this will give you a more defined silhouette.

STYLEBOOK TIP: As you get styling ideas, save them in the notes of your Stylebook outfits.

Save Styling Notes
  1. Select the outfit you’d like to add notes to
  2. Tap the notes icon in the bottom left
  3. Type your styling advice in the free-form notes field and tap Save
Shopping

When I’m shopping for new pieces, I do a lot of planning. Good planning results in buying items that fit well and match the clothes I already own. It seems like a lot of work but at the end of the day I’m way more satisfied with my wardrobe - and I've made fewer purchases that I regret! Here are the steps I take:

  1. Notice a wardrobe gap and determine what type of item you need to fill it
  2. Start to look for inspiration online
  3. Do a broad search for that type of item want within your budget
  4. Narrow down your choices and add the items to your Stylebook wish list
  5. Sign up for sale emails and alerts via ShopStyle
  6. If it’s possible, try on your favorite options at the store
  7. Narrow down your choices, then purchase your favorite item
  8. Bring the item home and try it on with your actual clothes - with the tags on, just in case
  9. Keep it, if it works well - or return it if it doesn’t fit your wardrobe

When I’m getting ready to make a purchase, I ask myself the following questions:

  • Was I planning to buy this type of item?
  • Do I already own something similar?
  • Can I use it in at least three outfits?
  • Does it fit well?
  • Does the color look good on me?
  • Does it fit my budget?

  • Knits: Cotton t-shirts and maxi dresses get a lot of wear so you want them to look great. Unfortunately, they can sometimes wear out faster than you want them too. I recommend shopping for these at Target. They consistently carry a few different styles that come in a lot of colors and their shirts miraculously don’t fade.
  • Bags: Buy the best handbag you can afford, because you’ll use it so often. And always look at sales. I set up sale alerts on my favorite brands and stores like Kate Spade, Neiman Marcus and Nordstrom. I never pay full price, and I always get a bag I love in my budget.
  • Leather Jackets: Nordstrom consistently has really great choices for under $500.
  • Denim: I buy skinny jeans from the GAP and since they frequently have sales, I just wait until I get a 40% off coupon. I splurge on bootcut jeans from True Religion because they magically make my legs look long.
  • Gym Clothes: Athleta has really cool casual jackets that don’t look like gym clothes. These are amazing because you can wash them in the machine and they still look fantastic.

NOTE: Posts in the Style Guides series include affiliate links to some of the products discussed.

To suggest a Style Guide topic, tweet to @stylebookapp.


GET THE APP
Download Stylebook
The closet organization app for the iPhone and iPad


Read More Style Guides