Outfit Planning – The Secret to Looking Good

It’s one of those things they don’t talk about, but the most fashionable people I know all plan their outfits in advance!  We all want others to think we are effortlessly stylish, but the truth is, looking put together requires a little thought. Want to look great in five minutes flat? Outfit planning is a stress-free way of making sure you feel great about your look every day

Maybe it seems a little “extra” to be planning your outfits for the week when your big plans are to hit Target and the sandbox.  But this isn’t about being unnecessarily fussy. What is it about?

  • Avoiding decision fatigue
  • Making your mornings easier
  • Being less frazzled
  • Feeling great about yourself

The real time suck: Indecision

I don’t think anyone would argue that putting clothes on is terribly difficult.  It’s figuring out what to wear that’s frustrating.

What pants goes with this top?  

Should I wear a skirt?

Do those fit right now?

Ankle boots or flats?

Screw it.  I don’t have time for this.  I’m staying in leggings. Maybe someone will think I work out.

But wait… if it’s this hard to come up with one outfit, how can you possibly come up with a weeks worth?

That’s where the capsule wardrobe and/or Stylebook come in.

Capsule Wardrobe

A capsule wardrobe is a pretty simple concept. It’s a bunch of clothes that all go together so you can mix and match to your heart’s content, and not have to worry. Every top works with every bottom, and you just switch them around every way you can.  

While this sounds like it could get boring and repetitive, you’d be shocked by how versatile it can be.  With 25 piece you could wear a different outfit every day for over three months.

But more to the point you could get dressed in the dark in 30 seconds and still know you will look good.  

You can design your own in my upcoming course, or if you are the kind of person who is thinking “Just tell me what to wear!” Then you can find clothing recommendations and complete outfits already put together in my capsule wardrobe shop (coming soon).  (If you don’t want to bother cataloguing all your clothes and figuring out how to put things together, that’s the way to go.)


First off, I have no affiliation with Stylebook.  I just love it.

Stylebook is an app that helps you put together outfits and schedule them.

If you’ve ever seen Clueless, it’s Cher’s closet app come to life.

Outfit planning - Cher's closet from clueless
Minus the leopard print. Sadly.

It can be a bit daunting at first to imagine adding all your clothes, but I find it to be a game-changer in terms of making the most of what I already own, scheduling it, and getting a sense of what I actually wear as opposed to what sits in my closet.  

outfit planning with stylebook
One of my outfits in Stylebook. I recommend wearing more than one shoe, for the record.

Sweater – $55 | T-Shirt – $25| Jeans – $99| Shoes – $70 | Belt (thrifted) | Necklace – $29| Earrings – $350

Necklace – $29| Earrings – $350

For me, outfit planning would be nearly impossible without it. Stylebook takes away the overwhelm of looking at my whole closet (and scattered accessories) and allows me to consider one piece at a time.  I can pick out a shirt and scroll through all the bottoms I own to see what I like together. I can see how an outfit looks without having to try things on.

How to get started

While I like to plan my outfits for the week on a Sunday, if you haven’t done it before, and are feeling overwhelmed, just start small.  Choose to have your outfit planned at least the night before two days a week. Try one weekday and one weekend day and set a reminder on your phone to make sure you get it done.  Lay out the clothes the night before and get out your jewelry/shoes/bag etc.

Then each week add another day.  So you could start out by planning your clothes for Wednesday and Saturday.  Then next week do Monday-Wednesday-Saturday etc.

Take note of how what happens on the days you wear your planned outfits.  Just mentally check in once or twice and ask yourself:

Do you look more put together?  

How do you feel about yourself?  

Are you more focused?  

How long did it take you to get dressed?  

The surprise benefit to outfit planning

While I understood why someone might plan outfits, it never occurred to me that I could enjoy it.  But the difference between trying to throw something together in the morning and planning it in advance cannot be overstated.

Rather than staring into my closet in a panic, I take time figuring out what I think looks good together.  I play with accessories and different ways to wear things I already own, and it becomes a fun creative outlet.  And I do all of this from my phone while watching tv rather than making a mess in my room.

Woman looking at her phone planning outfits
Perfect. I’m going to look awesome at Mommy and Me.

You know when you have an event coming up and you know you have a great outfit for it?  Or you just bought an awesome new piece of clothing you can’t wait to wear?

That’s the feeling outfit planning gives you.  You get to anticipate looking great.

I can’t wait for you to get started and see what a change this makes.  It’s absolutely the difference between just thinking about dressing better, and actually doing it!

PS – if you enjoyed this article, please share it on social media!

PPS – It makes sense to clean out your closet BEFORE cataloging things in stylebook or trying to create outfits.  Know what you’re working with!