Good, Better, Best: A Guide to Layering

Nov 27, 2023

I started this blog in 2008 to provide guidance to the thousands of Capitol Hill staffers who needed to dress for professional jobs on government salaries.  Over 15 years of blogging, some questions have proved eternal — the best tights, what to wear to a formal event, makeup tips for women who don’t want to wear makeup, etc.  But one of the most commonly asked questions is how to get good at layering and styling clothes.

This weekend, Sarah said something on Instagram that felt so true, “I hate styling and love to just wear clothes.”  Lord, if I didn’t feel exactly the same.  So if you’re with us in this boat, Good, Better, Best is the feature for you.

Good // A great pair of jeans and a striped shirt are a do-anything, go-anywhere outfit.  The plane.  Casual Friday.  The in-laws for dinner.  Shopping on Saturday.  The combination just does it all.

Here, I started with these Paige Anessa wider leg cropped jeans with a raw hem.  On me, with a 31.5 inch inseam, the jeans are ankle length.  Your mileage may vary.  But they also make a similar full length version.  Need a more affordable choice?  Try these from Out from the Kloth.

After that, I added this great, $17 turtleneck in an easy black-and-white stripe.  For splurgier version, try this one from Bergdorf’s. Plus-size? Eloquii has you covered.

Better // This outfit from Atlantic-Pacific has been living rent free in my head since she first posted it five (?) years ago.  I love the look of a turtleneck sweater in a chunky knit layered over a thin, striped tee.  Push the sleeves up, and it just makes the look more polished and more interesting.

To achieve that same vibe, I added this great sweater from LL Bean (also in petite and plus).  I love the subtle, waffle texture on the yoke.  They also make a wonderful casual option with a funnel neck and drawstring ties.  The J.Crew Factory top gives you the same cable knit vibes in a sweatshirt.

From there, I added my absolute favorite boot of all time.  I cannot say enough good things about these Blondo Tamera boots.  I wore them basically every day of winter 2023.  The thick bottom sole makes them comfortable, and gives you traction.  Even though they had a heel, I could walk the whole Capitol, climb stairs, hike to a restaurant, and push Sloane through the grocery store and never feel a thing.  Ah-may-zing.  They’re also waterproof, and come in four chic colors.  Of all the things I bought in 2023, they are — without a doubt — top five.  Maybe top 3.

Finish off this look with an easy earring.  I love the relaxed look of these $52 enamel hoops from Wolf & Badger. If you’re not familiar with W&B, they’re a department store for independent brands.  They always have well-priced, unique items.

Best // To complete the look, I thought about a green, boucle overcoat.  Then, I thought about a mustard blazer or top coat.  But I settled on this olive leather jacket from Whistles because it had the cool, but understated, look I was going for.

For a more relaxed look, I like this bomber jacket on sale at Athleta.  I also really love this notched lapel cropped blazer as a topper.  It gives it a modern, Gen Z vibe that’s still approachable.  Also, if you’re in the market for a leather jacket, Madewell’s is 60% off today.

Add to this a cool pair of sunglasses and a sharp bucket bag for that laid back, but work appropriate style.  As for the hair, I would wear it up so that it’s not competing with the turtleneck neckline.  And for the makeup, I would keep it simple and fresh with a bit of berry or rose lip color and a hint of mocha shimmer on the lids.

{this post contains affiliate links that may generate commission for the author}

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  1. MXJ says:

    Yessss. This is the type of post I love! Thank you!

  2. Cait says:

    When you buy clothes do you size up/down with these outfits in mind? For this outfit I’d prefer the striped shirt to be pretty tight-fitting, but for regular wear I’m more comfortable with a looser fit, so I’d really need 2 shirts- one for layering and one for not. Same with the moto jacket- I’d prefer a tailored fit, but would need almost a full size larger to fit over the sweater here. But that seems to defeat the point of buying versatile pieces. Do you typically decide whether it’s for layering or not when buying a piece, or do you sometimes buy things in multiple sizes?

  3. Danielle says:

    Love this type of post! Look forward to more.

  4. Shannon says:

    I agree about the styling. I just can’t seem to pull some of it off, like the tucking-in sweater thingy. Ugh! Love these outfit ideas though.

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