Quick hit style tips: Weekday leggings but make it cute

Outfit inspo, but make it realistic.

(Psssst hit “play” above to hear my voice recording of this post!)

Today’s OOTD: Wore to drop-off, on a run/walk, to pick up and swimming lessons. Leggings and sweatshirt c/o (both run TTS, I got smalls in the leggings but a medium in the sweatshirt because I like room in sweatshirts), very old striped sweater but lusting after this version from Sezane, Bombas socks (try code JESSKEYS21), Kizik sneakers c/o (run TTS for me! Try my code JESSKEYS15 to see if my Kizik discount still works!), baseball cap, Clare V Grande Fanny and bag strap.

Gooood morning!

How is your week going so far? My mom is visiting this week from Oregon (she’s here until Saturday) and I’m excited that she’ll be spending Halloween with us! June is being Chase from Paw Patrol so our stint of darling halloween costumes that I get to choose is now over. It was a good… 2 year run?

I was so happy to see our first Substack group chat kick off with some great content requests! I’m not sure why I was surprised to see that “easy casual style tips” was one of the most requested topics–but it’s one I am HAPPY to elaborate on, it got me thinking about simplifying in general–and that it has dawned on me recently that the best way to make life better/easier/more meaningful in any way is just…SIMPLIFY.

Simplify everything. (Good god, especially MOTHERHOOD. That’s another topic for another day.) Less activities, less STUFF, less googling about milestones, less toys, less feeling like I need to entertain my kid, less caring about how much or what she’s eating or whether me doing this or that is going to bite me in the ass later or have long term effects.

Just LESS OF IT ALL.

And know what? I think that’s a good rule to apply to getting dressed, too.

Less trying to fit a square peg into a round hole, less feeling like I “should" wear “real clothes” and like part of me should be sad or embarrassed about the fact that I wear leggings most days of the week. 😂

So I thought I’d share some thoughts on how to make your weekday outfits just a little bit better. SIMPLY.

Nothing here is rocket science, but the little things add up to make you feel a lot more pulled together.

And I think a lot of us are in this phase of life where comfortable outfits are just where it’s at–and that’s something that should be embraced. But also, it doesn’t mean “giving up” on feeling stylish either!

As Paisleigh said in the chat, “my mood is so much better when I’m in a comfy but also classy outfit” and I could not agree more. (Now of course, there are times I fully embrace working from home dressed like an absolute gremlin, but a few too many days of that can really be a shot to the old self esteem!)

P.S. Come over to the chat and weigh in with what content topics you’d like to see here on Substack! ♥️

If you’re also in a constant rotation of leggings and workout wear, and want to know how to make your outfits a little more pulled-together, today’s post is for you!

How I make my casual weekday (er, leggings) outfits just a LITTLE bit more stylish:

1. Add an unexpected extra layer:

One of my most utilized style tips as someone who now generally lives in leggings most days of the week: pairing “non athletic elements” with an otherwise “athletic” outfit is an easy way to make it look less “I came straight from the gym” or “I couldn’t bother to get dressed” and more like, “I meant to do this.”

The easiest way I’ve found to do this is to add a third layer. (My friend Anna always talks about this too!)

This could be a jacket, vest, or simply just a sweater tied around your shoulders.

In this instance, it’s a chunky striped sweater thrown over my shoulders. (The one I’m wearing here is very old but I am lusting after this version from Sezane.)

Is a sweater thrown over a sweatshirt redundant or a cute accessory? Who is to say? 😂 But I think draping a sweater around your shoulders instantly makes you look like a rich lady and as you know, I like to lean into the Nancy Meyers wannabe lifestyle so here we are.

(Added bonus: Moms who don’t wear your favorite sweaters for fear of getting juice or milk or spit up or whatever all over them–here’s a way you can still work them into your outfit with less risk!!! 🙃 It’s harder to barf on something tied around your shoulders amiright?)

It also adds texture, it adds contrast, and of course, a little warmth. (It’s practical, I swear.)

As the weather gets colder and you’re pulling on your blazer or oversized coat (speaking of, I just ordered this Mango one I got last year in a second color I love it so much. Perfect layering coat. You can see my whole latest Mango order rounded up here.), I love the look of layering a sweater on top of that, too, for a very “posh street style” look without actually trying that hard.

As seen on Pinterest and Pinterest (remember this can be adapted for casual wear too!)

2. Match your top and bottom (monochromatic):

Sounds simple, but can make a big difference! Obviously a matching set is great (like this incredibly soft bubble hem sweatshirt and ribbed leggings from Athleta I’m wearing here) but this definitely NOT a requirement. (NO you do not need to go out and buy anything new! Go through what you already own and assess what can go together!)

For example: I love wearing my chocolate brown Quince boyfriend cardigan with chocolate brown leggings. Or black leggings with a cute black tunic-length sweatshirt (or my black Dudley Stephens Park Slope tunic fleece).

Add your "*third layer* and this combo makes you feel like, “cute casual running errands” you instead of, “I’m late for class and just rolled out of bed” you.

3. Cute socks:

Socks are a bit of a mystery these days (what length do you get if you’re branching out from no shows!?)

I’ll make it easy: the Bombas modern rib quarter socks (their vintage striped socks are also really cute, which is actually what I’m wearing in this photo, but I wear the modern rib quarters more! My Bombas code JESSKEYS21 should get you a discount–fingers crossed it’s still live!) They go with everything from running sneakers (yes, I work out in them!) to regular sneakers to loafers.

This is probably a bit niche, but I also really appreciate that they are a “soft white” color because I wear a lot of tan and often times “white white” socks look bad (almost blueish!?) in contrast.

They hug your feet like literally nothing else and TBH maybe you shouldn’t buy them because then you’ll be left hating all other socks and you’ll be suckered into buying fancy socks for the rest of your life. (Please note that Bombas is a sponsor but they did not pay me to talk about this!! They’re just that good I promise!)

4. Get yourself a couple nice, neutral baseball caps:

I swear by these Amazon baseball caps. (Note I’m actually wearing an Aritzia baseball cap here that I don’t like as much as the Amazon one because I left my beloved tan Amazon baseball cap in South Haven but this reminded me to order another–so just trust that the Amazon is better okay? 😂)

This is my rule for all accessories in general–having a few varying color options of nice hats, gloves, scarves, coats, etc, because there is no quicker way to ruin an otherwise perfectly great look than putting on accessories that don’t go with your outfit and having you look like a 5 year old on the playground.

I love a baseball cap because it covers my dirty hair AND acts as a much-needed accessory to make a regular old outfit look a little more intentional.

(As someone who spent middle school and high school in Arizona and then moved to the Midwest for college, I learned this pretty quickly, and there is nothing I hate more than feeling like I look like a little kid at recess. 😂 Maybe this is just a me thing? But I feel SO much better when my accessories ADD to my outfit, and don’t take away from it!)

5. A great everyday neutral lip color:

It might sound odd to have a go-to lip color for when you’re wearing leggings, but a swipe of Merit’s lip oil in “Marrakech” (what I’m wearing above) always has me feeling a lot more put together and keeps lips so hydrated. (Think moisturizing, not sticky!)

They have tons of great colors, but this one is my favorite. These days, my makeup routine just consists of sunscreen, mascara, and a swipe of this gloss, and I’m out the door.

6. A practical but elevated everyday purse:

When I switched my everyday purse from being a sporty fanny pack to the Clare V Grande Fanny all of my outfits got an instant upgrade, yes, even the athleisure ones!

I am truly obsessed with this bag and everyone I meet (in my DMs or real life) who pulls the trigger on one feels the same. I held out buying it for years because of the price, but it’s easily one of the best investments I’ve ever made in terms of cost per wear. (Also, their customer service is really great. The strap of my first bag mysteriously broke off but they just gave me a brand new one zero questions asked!)

It’s the perfect size, it holds everything you need but isn’t too big, it keeps your hands free, is very lightweight, and I love that you can swap out the strap to create a totally different look with every outfit.

Hope this was helpful and that you have the BEST day and a happy Halloween! ♥️ What are your favorite tricks to elevating your everyday outfits?

xoxo

Jess

P.S.S. Wanted to make sure you caught Mango is running 30% off right now. They are a hidden gem for fall/winter stuff in my opinion–here’s what I ordered!