Your Most Pressing Fall Styling Questions — Answered

As a writer who covers fashion, it’s a common occurrence to be on the receiving end of style-related questions from friends and family. Whether it’s one of my sisters asking where they can find a pair of boots for the new season or my aunt inquiring about what sort of dress she should buy for an upcoming wedding, this feeling of being ‘on call’ with all things fashion related is something I’ve grown accustomed to. And being the resourceful journalist that I like to think I am, I decided to funnel all of these recent fall styling questions directly over to one of my favorite experts for a second opinion: Joyce Lee. She’s the SVP of design at Madewell, a brand that, over the years, I’ve returned to for inventive-yet-approachable styling ideas. If catalogs were still a thing, I’d be its top subscriber solely for the outfits.

Culling a dozen or so fall-related style questions from friends and family, I handed these inquiries off to Lee to see how she’d tackle their queries — styling even the trickiest items in a relatable way. Ahead, get the scoop on how to wear seasonal trend pieces like sweater vests and baggy jeans as well as useful tips on topics including accessorizing with socks and smart layering tips for unpredictable weather. If you’ve been feeling uninspired by your fall wardrobe, get ready to revitalize your love of dressing.

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Q: What are some fun ways to style a sweater vest?

“I’m loving the sweater vest as a new versatile fall and winter layering piece — there are so many ways you can style it,” Lee says. When the weather is warmer, she wears by it on its own as a cute top. “As it cools down, I’ll style it over a tee or easy button-down shirt,” she says. “I’d also suggest trying it over a dress to make it cozier and to add some texture.” Try tucking in just the front for a cool-casual styling choice.

Q: What are the big boot trends for fall?

“Lug soles, sportier outsoles, and uppers with performance attributes are huge right now,” Lee says. “I also like tall shaft boots — they’re a classic fall wardrobe staple.” Try pairing them with looser pant silhouettes or a fitted sweater dress.

Q: How do you transition summer dresses to fall?

When transitioning to a new season, finding unexpected ways to wear your favorite pieces from the season prior is an easy way to keep your wardrobe tightly edited while also weather appropriate. “I love a poplin dress with a sweater vest layered on top and tall shaft boots,” Lee says. “It’s the ultimate fall transitional look!”

Q: What shoes do you pair with baggy pants?

Baggy jeans look especially cool this year, but they can also be particularly challenging to pull off if you’re used to skinny styles. Lee’s advice? Don’t overthink it. “I usually style my baggy pants with chunky loafers or sneakers, the juxtaposition just works.” The chunky footwear doesn’t get overwhelmed by the volume of the denim.

Q: Is brown a staple neutral or a trend?

Brown is a color that’s been trending as of late, but also happens to fall distinctly in the category of neutrals — so which is it? “Both! I’m always a fan of classic earth tones and feel like they are timeless, but browns are very strong right now, which makes me so happy.” Try adding the hue in classic silhouettes pared back to trendier items like a sweater vest.

Q: What are some heel alternatives that still look polished?

If you’ve laid off the heel-wearing over the last year, rest assured you can continue doing so while still looking polished. Lee has a few ideas to get you started. “So many great chunkier boots and loafers! They’re very on-trend right now, and there are so many ways you can style them.” For the office, try styling an ankle-high boot with trousers or a full suit. For nights out, loafers, tights, and a black dress are a classic combination.

Q: How do you layer when the temperature changes significantly from morning to night?

Temperamental weather is an unfortunate fact of autumn, requiring a bit more thought when it comes to planning an outfit. Lee recommends leaning on knitwear. “I’m loving sweater sets,” she says. “A great sweater tank layered under a cardigan is so comfortable yet still very stylish.”

Q: How can you dress festively for fall when your city doesn’t get very cold?

For those who live in warmer climates, it can be a struggle to dress festively for fall while not overheating. Lee knows just the thing. “Shirt jackets are perfect, and I also love relaxed blazers,” she says. “They’re so versatile and incredibly fun to style, you’ll be surprised at how many items they’ll go with that you probably already have in your closet.”

Q: How do you style socks in a cute way without feeling too collegiate?

“The collegiate prep trend is definitely in right now with all the pleated skirts and collared shirts we’re seeing,” Lee says. “If you want to tone it down a little, try cozy ribbed socks with chunky loafers and baggy pants.” Aim for a sock that hits just above the ankle bone, and don’t be afraid to play with patterns or colors.