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Style Lessons from a Favorite Outfit

April 16, 2024

Are you team Outfit Repeater or team Never the Same Thing Twice? I’m definitely a major outfit repeater. I find something I enjoy wearing and I have to force myself not to wear it again the very next day. And in my book there’s absolutely nothing wrong with that. I definitely have enough clothes in my closet, however, to mix things up. So I usually do wear different outfits throughout the week. But when I came across a new favorite outfit recently, I decided it was time to take a few notes and learn some style lessons. Here’s what I learned.

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If something’s worth repeating it’s probably also worth examining a bit. If you have a favorite style formula, shirt, style hack, set of jewelry, etc. that you like to wear on repeat, it’s smart to ask yourself, “Why do I like this so much? What is it about this thing that resonates with me?”

Lessons from a Favorite Outfit
jeans (more economical option) // button-up shirt (more economical option) // sandals // belt // shoulder bag (more economical) // necklace // bracelet // earrings

Now this is not the same thing as being in a rut. When I’m in a style rut I do indeed find myself wearing the same things over and over, but I’m generally a little miserable about it, too. In my experience, a style rut has me wearing similar things over and over because I’m tired of my clothes, they don’t fit my lifestyle, I’ve made bad purchases or the things in my closet no longer fit my body.

But in this case I’ve come across a very casual outfit that feels amazing on me, looks pretty good (in my humble opinion) and truly makes me happy. Can you relate? If so, maybe consider that outfit as I talk through a few style lessons I’ve learned from a favorite outfit.

Lessons from a Favorite Outfit

Style Lesson 1 Learned from a Favorite Outfit

Style lesson number one is simply that lifestyle rules. We talk a lot here about dressing stylishly, being abreast of the current trends and knowing how to dress your body type and proportions. But truly, having plenty of outfits in your closet that really work for your real lifestyle? That’s where the magic begins! For more reading on this, check out Define Your Style for Your {Real} Lifestyle. It’s part of our Define Your Style…Refine Your Wardrobe style series.

My real lifestyle is super casual. Most days I’m at home working from my home office, puttering around the house and maybe getting out to run a few errands or meet a friend for lunch. And that’s okay. So my closet needs to reflect that. This favorite outfit definitely works for my real lifestyle.

Style Lesson 3 Learned from a Favorite Outfit
jeans (more economical option) // button-up shirt (more economical option) // sandals // belt // shoulder bag (more economical) // necklace // bracelet // earrings

Style Lesson 2 Learned from a Favorite Outfit

I don’t have the bandwidth anymore for clothes that aren’t comfortable. That’s all-important lesson number two. Remember, comfortable is not a style angle. In the style series post entitled How to Define Your Personal Style we talked about using three style angles to define your style. But I encouraged you there not to use the word comfortable as one of your style angles. That’s because comfortable isn’t a style; it’s a setting, a situation, an event.

Lessons from a Favorite Outfit

If you use comfortable as a style angle you’ll shop through the lens of comfort instead of style, and you’ll end up looking frumpy, tired and a little worn out. Instead, shop through the lens of three true style angles – words like elevated, elegant, sporty, boho, romantic, classic, timeless, preppy, minimalist, etc. – and you’ll actually build a closet that has style oozing through it!

That said…as I shop for clothes that are classic, elevated and effortless (my three style angles) I insist that every item I add to my closet also be comfortable. So while comfortable isn’t one of my style angles, it is a gatekeeper of sorts. Make sense? Lesson learned? I’m done with uncomfortable clothes, shoes and accessories. And there are plenty of beautiful garments and shoes out there that are both stylish and comfortable.

Color Sets the Tone
necklace // bracelet // earrings

Style Lesson 3 Learned from a Favorite Outfit

The next lesson learned from a favorite outfit is that my jewelry collection needs to reflect and work with the clothes in my closet. Building a jewelry collection can be a little tricky. For some reason in the past I tended to just buy baubles that struck my fancy with little regard to how they would work with my clothes. Can you relate?

Style Lesson 2 Learned from a Favorite Outfit
necklace // bracelet // earrings

Honestly, this is something I just hadn’t even thought about much. But in recent years I’ve been slowly trying to fill my jewelry box with pieces that really resonate with my style and also promise to work nicely with my necklines and the colors in my wardrobe. These new Julie Vos pieces are some I’m going to be wearing on repeat!

Style Lesson 4 Learned from a Favorite Outfit

A set of cognac accessories will elevate every casual outfit like nothing else can. That’s the next lesson I learned from this favorite outfit. Well, actually I already knew this one. But this cheerful print shirt and jeans combo is a great example of how cognac sandals, belt and shoulder bag (more economical) can really take a casual look to the next level.

Cognac Accessories are an Instant Outfit Elevater
sandals, belt and shoulder bag (more economical)

Trust me. This works every time. My three accessories don’t match exactly. But they’re pretty close. Soon I plan to share a post all about building accessory sets. No, your shoes, belt and handbag don’t have to match or be the same color. And sometimes I prefer it that way, as in this blog post where I combined ivory and black accessories. But during the spring and summer, my favorite accessories for casual outfits are cognac. Lesson learned!

sandals and shoulder bag (more economical)

Style Lesson 5 Learned from a Favorite Outfit

When you see a beautiful piece in the colors you love…buy it! Obviously there are some caveats to that lesson. But for this gal who tends to stick with her neutrals, I’m learning to lean in to color a little more. Yes, I’m all for having your colors analyzed and wearing the ones that suit you best. And once you’ve done that, I’m even more for narrowing down your color palette so that you can build a cohesive closet. But once those things are done, it’s smart to look for some beautiful pieces in those colors that bring you joy. You don’t need many, but you do need a few. These are the ones you’ll enjoy wearing over and over!

jeans (more economical option) // button-up shirt (more economical option) // sandals // belt // shoulder bag (more economical) // necklace // bracelet // earrings

Do you have a favorite outfit or two that you’re wearing on repeat? I encourage you to take the time to ask yourself why. Remember, if it’s worth repeating, it’s worth investigating a little. You may learn a few style lessons that help you put together additional outfits you love just as much!

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Blessed for My Day

None of us enjoy being disciplined by an authority. I’ve only been pulled over by a police a couple of times, and both times were for running stop signs. Or rather, rolling through them. You know how that goes, right? You acknowledge the stop sign, but fail to completely stop. You figure you’re being safe enough, checking both ways before you proceed. But honestly, you didn’t obey the sign. You didn’t stop. Yeah, that was me. (A long time ago, mind you!)

By nature I’m really a rules follower. So getting pulled over and issued a ticket hurt me on so many levels. I don’t like being told I’ve done something wrong. But honestly that’s the wake up call we need sometimes. Otherwise we continue to do the thing that is not right but that we have been getting away with. If God has called you out for something and it gets all over you…I get it. It’s uncomfortable, embarrassing, a little humiliating. But it’s for our own good. Trust your Good Father. He knows what He is doing.

It is for discipline that you endure; God deals with you as with sons; for what son is there whom his father does not discipline? But if you are without discipline, of which all have become partakers, then you are illegitimate children and not sons. ~ Hebrews 12:7-8

xoxo, Kay
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8 thoughts on “Style Lessons from a Favorite Outfit

  1. What a good point I hadn’t thought of before. I am going to give it some thought on an outfit I am gravitating towards and why! That will probably help me with my settling on my third style angle. I have two for sure and not sure about third. It has already helped me with some clothing purchases!
    Thanks, Kay

  2. Loved this post, Kay! I have been working on defining my wardrobe since all of us started this new outlook. I finally made an appointment, like you suggested, with the manager of our Talbot’s here in Boise. I told her I wanted to develop a truly workable style for retirement. I have a base in indigo and white, she had everything ready. She taught me how simple it was to add jackets, tops and, pants in casual cuts, and fabrics. She also threw in a couple of casual skirts, so I could see how easily everything I purchased could be dressed up or down and be used for many different occasions. I wanted to purchase everything,of course, but we settled on the perfect few. Can’t wait for your posts on accessories sets. Thank you so very much for all the helps you give us, Linda

  3. I never put too much thought into what I was buying or wearing. That said I have a small amount of clothes I’ve never worn with tags still attached just sitting there taking up valuable space. And making it look like I’ve got more than enough clothes. I have really learned a lot from this post. Thank you.

  4. Kay, that blouse so looks like you! One of my favorite choices from all your selections! The pink lipstick is so lovely and brings out the pink in the shirt. Enjoy your visit with your daughter and granddaughter.

  5. It really is a good thing to know why you like something, and also why you don’t like some things so you can do a better job just buying what really suits you rather than winding up with a bunch of stuff you don’t use! I’m trying to understand this because I want to keep my clothes simpler but more effective – I have things that I might only wear once a year, not enough to earn their space in the closet. Regarding BFMD, those things that hurt us instruct us, according to Benjamin Franklin. I got pulled over with my children years ago when I was in a hurry to get them to school for turning left on a “pink” turn signal i.e., almost red (I still think it was yellow, but I wasn’t the boss of the situation, LOL). Anyway, my young son burst into tears because he thought I was going to get arrested and go to jail – not the best way to start the school day!! It wasn’t exactly my heavenly father giving me a warning, but it worked just the same – I like to think I’m a better driver as a result and that’s hopefully good for anyone around me.

  6. Kay, I think I will be repeating wisteria purple this summer-your sweater and shirt combo had me looking at this with Talbot’s, and I went with the denim jacket and shell in that color. Thank you!

  7. Team outfit repeater here. More correctly, team outfit formula repeater. When I find a formula that works, I wear it on repeat. Additionally, I think along the way, I’ve learned many of the same lessons you mentioned.

    I love what you said about comfort not being a style angle, but a gatekeeper. That made perfect sense!