“Laid-back classic” styles to wear now and later

Pre-fall pieces from Madewell: plaid blazer, charm bracelet, pearl earrings, lug-sole loafers, color-blocked bag.

I hadn’t been paying much attention to Madewell lately, but some of the new styles I spotted this week have put them back on my radar. The pieces that caught my attention lean into that “laid-back classic” aesthetic that they do so well.

Above: bandana | tee | earrings | jacket | bracelet | jeans | shoes | bag

Pre-fall has always been my favorite fashion season, for a few reasons. First, because the pieces in these collections are often the most wearable in our climate for several months out of the year. The fabrics tend to be lighter, and the cuts a little more relaxed.

And I don’t know about you, but by mid-August, my summer wardrobe feels a bit stale. So I like to keep an eye out for lightweight pieces and accessories that I can wear now to freshen things up, and that will transition into fall.

Longer, relaxed blazers and jackets are still very much on-trend. They add some polish and structure to casual outfits without looking too trussed up. In lighter weight fabrics they’re a great transitional-season option. They can function as outerwear early in the fall (or almost year-round in some climates) or layer under an overcoat later.

Here are a few more options:

I love the look of that color-blocked bag (though it’s also available in solid black and brown) and have pre-ordered it to try. (Ships later this month.) And if I hadn’t just ordered a different pair of lug-soled loafers, I would have jumped on these.

And I’m always on board with an un-stuffy take on pearl earrings. (These are freshwater pearls.) That little charm bracelet coordinates nicely without being too matchy.

I’ll be back on Friday with my travel wardrobe for our upcoming California road trip. And next Tuesday, I’ll be doing an Instagram Live with Manina of Red Leopard. We’ll be comparing travel wardobes (she’s in France, I’ll be in Big Sur). Details to follow…

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  1. Hi! Great post, as usual. I love the Madwell Stovepipe jeans … and they come in tall!!
    The link for the 4 jeans styles doesn’t seem to work.

  2. Thank you for these delightful photos and some very nice options. I can’t open the items you post because of my ad blockers so I always go directly to the site to review them. In this case, I went to Madewell. In the past I’ve purchased many items from them but I have to be honest, if it was not for your depiction and display of these items, I would never have selected them directly from the Madewell site. I completely dislike their format. It feels unwelcoming and almost angry. I know it appeals to a younger shopper but it is not pleasant to review. Your layout is much much nicer. Thank you.

  3. I love the big blazers and your outfit pictured really looks appealing but whenever I try to wear them they add pounds and make me look much heavier than I am. I really don’t know how to fix that. It is a shame because I love the look.

    1. Hi Tina, one thing you might try is to keep the rest of the outfit fairly fitted (not flowy or oversized) and wear the blazer open. Rolling or pushing up the sleeves so wrists are exposed can add some definition. You can also try wearing a column of color underneath.

  4. I just love the items you picked from the madewell site (except the short tee). Classic but fun.
    Will check out their site as some of your other correspondents were not pleased with it.

  5. Do Madewell shoes run narrow or wide?

    Love the blazer, although double breasted is not my style. Reminds me of Everlane’s blue checked Mac cotton raincoat from a couple of seasons ago and I’ve been looking for it on resale sites in a larger size.

    1. The last pair of Madewell shoes I tried seemed to be a true Medium. But I haven’t tried this particular style.