How to Nail Transitional Dressing, According to a Stylist

How to Nail Transitional Dressing, According to a Stylist

March 28, 2025

Ah, transitional dressing—that tricky time of year when one minute you’re freezing, and the next, you’re sweating in your knitwear. Moving from winter to spring can be a fashion minefield, but with a few smart styling tricks (and a little help from the biggest S/S 25 trends), you can master the art of layering, colour play, and outfit versatility like a pro. Online fashion destination SilkFred’s Head Stylist, Megan Watkins, shares her go-to tips with us for nailing that in-between season style.

Oversized Khaki Green Rouched Sleeve Blazer

1. Layer Like a Pro

Transitional dressing is all about layering with intention. Think lightweight outerwear—a trench coat, a leather jacket, or a light blazer—as your new best friend. These pieces provide just the right amount of warmth without weighing you down. And if you want to tap into that Saint Laurent and Chloé-inspired boho trend? A flowing maxi dress with a structured blazer gives you the best of both worlds.

Megan reveals: “Layering doesn’t mean throwing on everything at once—balance is key! If you’re going for an oversized blazer, keep the layers underneath sleek and fitted.”

Long Sleeve Dobby Spot Blouse In White

2. Swap Heavy Knits for Sheer Layers

Still clinging to your chunky knit? It might be time for an upgrade. Sheer dressing is one of S/S 25’s biggest trends, so start incorporating mesh tops, organza blouses, and semi-transparent layers into your wardrobe. Layer them over camis or under dresses for a light, airy feel that still keeps you covered on chillier days.

Megan recommends: “A sheer top layered under a dress or blazer adds texture and interest—perfect for those unpredictable March and April temps.”

Navy Long Sleeve Jumpsuit With Chiffon Sleeve

3. Play with Colour

Spring calls for a colour refresh, and the S/S 25 palette is packed with mood-boosting shades. If you’re easing out of winter neutrals, tea rose pink, marigold, and periwinkle are great entry points. Want something bolder? Frog green and cardinal red are made for making statements.

Megan adds: “If head-to-toe brights feel too much, start with a colourful bag, shoes, or even just a bold lip.”

4. Rethink Your Footwear

It’s time to give those knee-high boots a well-earned break! Swap them out for ballet flats, loafers, or pointed-toe kitten heels. And if you’re not ready to let go of boots completely? Try ankle boots with a lighter, flowy dress to bridge the seasonal gap.

“A shoe switch-up instantly changes the vibe of your outfit. A slip dress with chunky boots feels wintery, but swap them for ballet flats, and boom—instant spring chic.”

Stone Viscose Linen Look Midi Shirt Dress With Wooden Belt

5. Introduce Lighter Fabrics (But Keep the Structure!)

Winter wardrobes tend to lean into heavier fabrics like wool and thick knits, but spring is all about breathable textures. Enter linen, lightweight cotton, and soft tailoring. And if you love a bit of drama? Power-pouf dresses and sculptural silhouettes are set to dominate this season, giving you structure without the bulk.

Megan says: “Mixing textures is a great way to transition—think a wool skirt with a sheer blouse or a structured blazer over a floaty dress.”

6. Embrace Skirt-Over-Pants Layering

Yes, really! The skirt-over-pants look is back, and it’s the ultimate transitional hack. Think sheer midi skirts over tailored trousers, or even a mini skirt layered over wide-leg denim for an effortless Y2K-meets-Parisian feel.

Megan adds: “It’s a bold trend but surprisingly wearable. Start with a sheer slip skirt over tailored trousers and keep the top simple.”

Bomber Jacket In Khaki

7. Invest in a ‘Wear Everywhere’ Jacket

A trench coat, cropped leather, or a relaxed blazer is the easiest way to pull together an outfit while staying practical. Look for olive, khaki, or even a buttery chocolate brown for an elevated, modern feel.

Megan shares her top tip: “A great jacket makes all the difference—throw it over jeans and a tee, a maxi dress, or even tailoring, and you’re set.”

Transitional dressing doesn’t have to mean suffering through weird weather in the wrong outfit. With a mix of layering, seasonal colours, and clever styling, you can effortlessly bridge the gap from winter to spring—all while tapping into the chicest trends of S/S 25.

Charlotte is the founder and editor-in-chief at Your Coffee Break magazine. She studied English Literature at Fairfield University in Connecticut whilst taking evening classes in journalism at MediaBistro in NYC. She then pursued a BA degree in Public Relations at Bournemouth University in the UK. With a background working in the PR industry in Los Angeles, Barcelona and London, Charlotte then moved on to launching Your Coffee Break from the YCB HQ in London’s Covent Garden and has been running the online magazine for the past 10 years. She is a mother, an avid reader, runner and puts a bit too much effort into perfecting her morning brew.