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Outfits in Real Life: Updating an Old Favorite

When I have to get dressed in a hurry, which is every time I try to leave the house these days, I rely on a few basics principles. 

The first is obvious but often over looked: have what you need.

Meaning, have multi pairs of the pieces you frequently wear, so if one (or two!) are in the laundry, you can still put an outfit together.

Second, play with neutrals. You can create a simple but elegant look so easily if you pair neutrals together. Don’t be afraid to mix black and navy or black and tan, grey and brown.

They all go together. 

Finally, work off a base and add layers. I don’t do this all the time but is has proven to be the best way to get me out the door without a lot of fuss. 

Outfits in Real Life: Updating an Old Favorite

That’s just what I did with today’s featured look, while updating an old favorite outfit formula. 

It’s nothing special, but I wore it on Friday for a to Bucks County with Bri and the girls. We stopped at our favorite farm, bought our tree (if you’re local, Bucks County Gardens had a fantastic selection), and grabbed some dinner.

And it was as adorable as it sounds.:)

The weather was mild but chilly, so this layered look was perfect. 

I started with this Amazon Essentials Turtleneck. It’s on sale today for $13. Yes. 1-3 dollars. 

I have it in black, tan, and ivory, in multiples, and wear a large, which gives me a little room. 

They wash well, with no shrinking or fading. 

Then, a pair of fleece-lined leggings.

This pair is also from Amazon, on sale today for $28 (usually $36), and come in a wonderful size range, XS – 3X, with over 20,000 FIVE star reviews. 

Of course, you can wear any legging you like, including a faux leather pair for some interest, but these fleece-lined ones keep you warm and feel cozy. 

For boots, you have a few options. I’m wearing the Miller Water Resistant Chelsea Boot by Caslon at Nordstrom. They are sold out in black, but I know so many of you have them, so here they are “in real life.” 

If you like their look, Sam Edelman has an almost identical pair in black with brown trim in all sizes

You could also wear a pair of flat-knee boots or even a pair of black slip-on sneakers. 

And that’s our base.

Now, there’s currently a lot of chatter on social about how to take the early 2000’s look of a vest/legging or skinny jean/ boot, perhaps the original outfit formula, and update it. 

Styles do evolve, and we want to look current.

So we can do that in a few ways. 

Here, instead of a puffy bright colored vest, we’re working with a slim fitting vest in a rich neutral.

And I ADORE this vest from J.Crew, another best-selling piece you probably already have in your closet. 

The tan (above) sold out, but you can get it in black, navy, and ivory at more than 60% off. Sizes are selling fast. 

Layering the vest over a body-skimming turtleneck, instead of how we used to wear them, over long tunic sweaters or flannel button-downs, is also a bit more current. 

Don’t love a turtleneck? Opt instead for a crewneck sweater. The Quince $50 Cashmere Crew works well here too. 

Then I added a scarf because I always have a chill.

But instead of a heavy blanket scarf, I’m wearing a traditional, oblong scarf looped around my neck and tucked under my vest. 

I’m wearing a splurgy-splurge from Burberry that I bought over 10 years ago. It still looks like new; the quality is incredible. 

For something much less, Amazon has a pretty awesome dupe. 

Back in the day we’d wear our oversized bauble necklaces, maybe layer two of them! 

Today, I’m keeping it simple, with my everyday jewelry,
including our favorite Amazon hoops for $14,

And my best purchase of the season, the Pebble Coach Crossbody.

The one I’m wearing sold out, but this one is in the same leather and is similar in shape and price. 




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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Tracy Gray

Tuesday 29th of November 2022

Love how you put this outfit together. I have several turtlenecks from Amazon and love them!!! Great look-thanks

Megan Kristel

Friday 2nd of December 2022

Thanks so much Tracy! XXX


Tuesday 29th of November 2022

I also like to see you in real life outfits! This one is a winner!

Beth Crawford

Tuesday 29th of November 2022

I really love that you show us the outfits in real life. You are cute as can be and it helps us to see if we have things in our closet that might work. If not we can check your suggestions to see if they have the fit and color we are looking for. Thank you for everything you do to help us get dressed and get out the door !

Megan Kristel

Friday 2nd of December 2022

This is really kind, Beth, thank you xxx