We all do it. Everyday. Sometimes under more pressure and with more limited freedom than others. But pretty much every day, each of us wakes up, eventually walks into our closet or stands at our dresser, and gets dressed.
For some, this process is fun and exciting. For others, it’s dreadful and stressful and disappointing. And for still others, it’s a non-starter. It means nothing. And likewise, the way we present ourselves probably reflects whichever method to which we’ve prescribed.
As a disclaimer, I wear yoga pants. Often. When I’m working from home, rest assured I decline every video conference invite and suggest over the phone meetings instead. At home, I don’t often dedicate much time to fancying up my outfit or makeup.
When I’m at the office, however, I always put forth a meaningful effort ensuring I look pulled together and presentable for the day. Like it or not, I will be judged for the way I present myself. Hopefully I’m not being judged for the things I can’t control. But, if I show up at the office looking like a slob, my colleagues will probably assume I treat my work the same way I treat myself… like it doesn’t matter.
Meaningful effort doesn’t have to mean large amounts of time, especially if you develop a couple favorite outfit formulas that work for you. We can discuss outfit formulas in another post. Today, I thought I’d share a bit about the evolution of an outfit when I get dressed in the morning and how I arrive at my final combination before heading off to my office.
Step 1: Check the weather
Particularly because I live in the city and walk to work, knowing the weather for the day is imperative to making functional style choices. Will it be wet? Windy? Cold or hot?
It’s not atypical to check the weather a couple times each morning just to be sure I know what’s coming in the morning and what to expect on the commute home.
Step 2: Take a look at the calendar
Got a big meeting that day? Blazer. A low-key day of pounding through work? Cardigan and pants. Casual Friday? Jeans. You get the picture.
Step 3: Pick an item to work around
Start with something from the categories noted in Step 2. Is it the blazer, the jeans, the cardigan? What’s on the style agenda?
Head to that section of your closet and pick one, whatever strikes your fancy (unless, maybe, you wore it yesterday).
Side note: If your closet is an unorganized mess, stop here. It’s time to declutter, reorganize, and just get that mess in order. It will make a world of difference, I promise! Seriously. A messy closet full of pieces you hate will drive you nuts and destroy any attempts you make at an enjoyable (or at least bearable) streamlined morning style session.
For a little help, check out my Simple Approach to a Wardrobe Edit. After you decide what to let go, you can even make some money cleaning out your closet. There are lots of ways to do it, but I think this way is the easiest and least stressful way to pad your bank account.
If you need a little more motivation and direction to clear out the clutter, check out Marie Kondo’s books The Life Changing Magic of Tidying Up and Spark Joy. I appreciated both but found Spark Joy to be more tangibly helpful. Check out the single, simple tip I took away from Spark Joy that made a huge difference in the organization of my things.
Now that your closet is tidy, head to the section you noted. Blazers. Jeans. A cardigan, etc…
If you choose jeans, you may need to go back to step 2 and pick a second piece as well. Cardigan? Blazer? Blouse? What are you feeling?
Hold up the item against another section you’d pair it with. For example, hold the blazer up against your collection of tops that could go under the blazer. What looks good? What feels right? What makes you excited to put it on? Maybe you have a Pinterest board all about Blazers that you can search for inspiration? (If not, I do and you can check out and follow mine!) You’re welcome. 🙂
Step 4: Finish the outfit
Now with one half of your outfit determined, head to pair the other half. Chances are your selection may be a bit more limited now that it has to match pieces you’ve already chosen. Rest assured, limitations are helpful. They help make decisions less overwhelming and spark creativity. It’s true. Even Biz Stone, co-founder of Twitter agrees, and he’s had some pretty extraordinary creative success.
Step 5: Next up, shoes
Consider the weather, how much walking you’ll be doing, if the occasion requires fancier heels or more casual flats, and what the heck you feel like sporting. Toss them on.
Step 6: Take a look in the mirror
If you don’t own a full length mirror, it’s probably worth buying one. You could also snap a photo with your phone using the timer function if you’d rather not own the mirror. But you probably need to take a look at how the whole thing fits together. Lots of wrinkles? Make your legs look short? Too sloppy? Who knows. But if something doesn’t feel right, consider what’s not working. Then switch it.
Step 7: Create a lookbook (optional)
If you want to create a cheat sheet of sorts, write down or take a picture of the outfit once you’ve decided on one you like. Create a lookbook of your own that includes maybe 10-15 outfits. After three weeks of doing this each day, you’ll have a whole list of looks you can rotate that work for you, and you don’t have to think about what to wear until next season.
This is a little like the Get Your Pretty On Style Challenges. Alison does the heavy lifting of creating a catalog of outfits for you, remixing several pieces. Either way, having a reference guide to look back to can be super helpful and prevents you from having to recreate the wheel every morning. Why would we do that?!
To step away from the theory, I wanted to share an example of my experience going through these steps one morning not long ago.
Steps 1, 2, & 3: After checking the weather and going with my gut instinct, I knew I wanted to wear pants. I also didn’t have much on the agenda for the day, so I didn’t need anything overly fancy.
I only own three pairs of work pants, so I started with a slim selection (great!). Remember how constraint breeds creativity?
I chose navy pants because I could tuck this cropped style into a pair of boots for my cold, winter commute to work.
Step 4: I held those navy pants up against the section of blouses and tops I have, landing on this blue floral one. With these together, I knew I wanted to try a monochromatic look. So I started with this option above. (I don’t own navy shoes so nude flats proved best in order not to mess with the monochromatic vibe.)
Step 5 & 6: I snapped a few photos for the blog (or looked in the mirror if you’re not a blogger – haha) and checked out the final look. The cropped pants in combination with my flats made my legs look short.
Modifications: I changed my shoes, opting for heels, to lengthen my legs. Better.
But I still didn’t like the cardigan. It felt sloppy, despite having just ironed it. I knew a blazer would provide a more structured, pulled together feel. I pulled out a blazer that matched.
I found a look I liked!
Lastly, I did another check of the weather. It felt warmer than I had initially expected. I didn’t need to wear my heavy winter boots I had planned to don over my pants, but it wasn’t warm enough for exposed ankles. I exchanged the heels for a pair of boots (also in a similar color as the previous shoes, so not to throw off the color scheme that satisfied me).
I wouldn’t normally wear pants and flat boots to a big meeting at work. But this day, I had a couple small meetings with peers and a lot of time at my desk. The boots would work just fine for traditional business casual.
So this is it. This was what I ended up with after four iterations of the outfit derived from my initial idea.
Putting together a great outfit doesn’t have to be too time consuming every day. This may seem like a lot of work, and it did take me about 10-15 minutes to get to my final version. But having a style routine that works for you and makes you feel great will likely take at least a bit of upfront investment. That could be three weeks of putting together a style “lookbook” day by day. It could be spending 10 minutes every morning following a few steps to find what’s right for that day. Who knows. But just like anything in life, finding a perfect routine or consistent success and proficiency in anything doesn’t just happen. It takes a bit of effort either in planning or in execution (maybe both).
All that said, I don’t want to be a downer and propose that feeling great in what you wear to work has to be hard or prohibitively time-consuming. But a little effort in planning and paying attention can go a long way.
Cardigan – August Silk | Blazer – JCrew Factory | Pants – JCrew Factory | Blouse – Banana Republic (Easy DIY modification) | Flats – Cole Haan | Heels – Target | Boots – Aerosoles