What Does Transitional Dressing Really Mean?

Style Advice: How To Master Transitional Dressing, Layering Tricks To Prevent Bulking, And Inexpensive Ways To Make Outfits More Interesting.

Today’s installment tackles transitional dressing, the secret to non-bulky layering, and inexpensive ways to make outfits more interesting.

I often read about “transitional dressing,” but what exactly does that mean in terms of shopping each season? —Jasmine

Not too long ago, if the calendar said fall, it felt like fall outside, and women needed pieces that made the transition from season to season a more seamless pursuit. But with Mother Nature these days, you never know if you’re going to get a snowstorm in May or a heat-advisory alert in November. In other words, the modern way to get dressed is to focus on the weather, not the season.

This means following what I call the LMH formula: Light, Middle-of-the-Road, and Heavy. Every three months or so, invest in a trio of key pieces: a light layer, a middle-of-the-road item that works whether it’s crisp or bone-chatteringly cold outside, and lastly, a heavy piece of outerwear. (If you’re on the hunt for three LMH cornerstones, consider a cashmere knittrench coat or leather jacket, and a wrap coat.)

Then mix and match the pieces with stuff you already own, based on the daily forecast. The result is a closet with clothes that are ready for anything without sacrificing comfort. After all, who wants to wear a bulging puffer coat on a balmy 57-degree afternoon when a denim jacket will suffice?

Lastly, I’ll leave you with this, Jasmine: Resist the urge to skimp on these pieces. They’re meant to be wardrobe workhorses that you repeatedly wear. So it’s okay to spend a bit more than you normally would on trendy buys.

I want to do a better job of layering this season, but all of my outfits end up looking bulky and/or sloppy. Any tips? —Kelsey

One of my stylist friends lives in bodysuits during the fall because she likes to pile on the layers. Reformation, home of eco-friendly-but-super-fashionable clothes, currently has an inventory full of outfit-making styles, including ones with tie-neckopen-backlace-up, and even metallic details (all under $100, by the way!). They make a major difference when you pair them with jeans or pencil skirts or wool shorts. And if you add a chunky cardigan, for example, you won’t experience any bulk because you started the outfit with a sleek, streamlined foundation.

I’ll get right to the point: I’m bored with my style. But I’m on a budget and don’t really have the resources for an entire wardrobe overhaul. What are some inexpensive ways to make my outfits more interesting? —Vanessa

Style is all about the details, Vanessa. So if you nail the subtleties of your outfit, then you’ll find yourself immediately re-inspired by the clothes you own. 

And take it from a fashion editor, who’s expected to always be on, even though I’m often just as bored with my style as you are: It’s often the boredom that births the best outfits. Here’s how I deal: I set aside a weekend each month to “shop my closet.” I turn on some Beyoncé, transfer my favorite pieces from the closet to a clothing rack, and then lie my accessories on the floor. There’s something magical that happens when you start haphazardly mashing pieces up in search of something new. And don’t worry, you don’t have to go at it alone: We recently did a series of style hacks full of genius ways to rethink your wardrobe. 

But don’t just stop at your closet, though. If you’ve got a guy in your life, scope out his closet too, something Virginia, our social media director, isn’t afraid to do. It’s paid style dividends, as I found out when she came to the office last week wearing a vintage-y brown belt.

After I learned it was her husband’s, I asked Virginia about why it works with her style. “I don’t like to look too put-together, so I stole the belt from his side of the closet and started wrapping it around my dresses and high-waisted pants,” she says. “I use the excess leather to create a knot, and it’s the perfect finishing touch.” And guess what? As I’m writing this column, Virginia’s wearing the belt again—this time with jeans and a simple top—and looks as great as you’d imagine.

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