7 Transitional Outfit Formulas to Take You From Late Summer to Early Fall 2025

Every year around mid-August, I find myself standing in front of my closet, half excited for the cozy season ahead and half unsure of what to wear. The mornings are cool, but by the time I step out for coffee, the sun is blazing like it’s still July. That awkward in-between stage — when it’s not quite summer but not yet fall — can be one of the trickiest times for getting dressed.

Over the years, I’ve learned that transitional outfits don’t need to be complicated. In fact, the trick is to lean into a few outfit formulas that mix late-summer staples with early-fall layers. Think lightweight fabrics paired with knits, open-toe shoes with denim, or sundresses styled under jackets. These formulas not only make life easier, but they also help you get more wear out of the pieces you already own.

So today, I want to share seven transitional outfit formulas I swear by. These are the looks I’m reaching for this season, and if you’re building your own early fall capsule wardrobe 2025, they’ll give you plenty of ideas for mixing, matching, and layering.

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Formula 1: Slip Dress + Oversized Blazer + Sneakers

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If I had to choose one late-summer-to-fall uniform, this would be it. A satin or cotton slip dress feels light and breathable during the day, but when paired with an oversized blazer, it instantly reads polished and fall-ready.

Personally, I love reaching for a neutral-toned slip dress (think ivory, champagne, or soft brown) and throwing on a structured blazer in charcoal or navy. The contrast between the slinky dress and sharp tailoring feels very 2025 — minimalist but put-together.

For shoes, I swap between chunky white sneakers for daytime errands and block-heeled loafers when I want something sharper. Add a crossbody bag or a structured tote, and you’ve got an outfit that transitions seamlessly from coffee dates to client meetings.

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Formula 2: Linen Pants + Knitted Tank + Light Cardigan

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I’ve always believed that linen isn’t just for summer. One of my favorite tricks is reworking my linen pants into fall looks by pairing them with knit textures. For example: a cream knitted tank tucked into wide-leg beige linen pants, layered with a cropped cardigan.

What makes this work is the balance — you’re taking a lightweight fabric (linen) and anchoring it with fall-leaning textures (knits). To keep the look modern, I’ll often style this with strappy sandals if it’s warm or pointed-toe mules when the mornings get chilly.

This formula is also one of the best for workwear transitions. If your office is air-conditioned but the weather outside is humid, this look will keep you comfortable all day long.

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Formula 3: Midi Skirt + Denim Jacket + Boots

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Every transitional wardrobe needs a denim jacket moment — it’s one of those timeless pieces that just works between seasons. I love styling mine over a flowy midi skirt. It could be a floral skirt leftover from summer or a pleated satin midi for something dressier.

The secret here is the shoes. As soon as I swap sandals for ankle boots, the whole outfit instantly feels like fall. I usually choose suede boots in a neutral tone (taupe, chestnut, or black) because they’re easy to rewear.

For 2025, the updated touch is accessories: oversized hoop earrings, a soft leather crossbody bag, and maybe even a silk scarf tied around the bag handle for that Parisian flair.

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Formula 4: Wide-Leg Jeans + Striped Long-Sleeve Tee + Ballet Flats

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This one is giving me major “Pinterest-girl aesthetic” vibes — effortless, classic, and very wearable. Wide-leg jeans are one of my favorite fall wardrobe staples, and pairing them with a striped Breton-style top feels timeless but never boring.

To make it late-summer appropriate, I’ll tuck in a lightweight striped tee, then layer a trench coat or cropped cardigan when the temperatures drop. Ballet flats keep the look polished and very 2025 (since they’ve made a huge comeback).

This is one of those formulas that just makes me feel like the main character walking through the city. Coffee in hand, hair in a loose bun, and that easy Paris-meets-New-York vibe.

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Formula 5: Sundress + Chunky Knit Sweater + Knee-High Boots

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You know those sundresses you loved all summer but feel too bare for September? Don’t pack them away just yet. One of my favorite hacks is to throw an oversized chunky knit sweater over the top, almost like you’re turning the dress into a skirt.

I especially love doing this with floral or gingham dresses — the sweater tones down the summery vibe and makes it feel cozier. Add a pair of knee-high boots, and suddenly, your sundress is reborn as a transitional outfit.

Pro tip: if you don’t like the bulk of tucking sweaters into skirts, use a skinny belt underneath and fold the sweater over it. It keeps the shape neat without looking forced.

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Formula 6: Leather Trousers + Cropped Top + Longline Coat

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This one is for when you want to feel a little more elevated. Leather trousers have become such a 2025 wardrobe essential because they strike the perfect balance between edgy and chic.

I’ll usually style mine with a cropped knit top (so it’s not too heavy) and then layer with a longline wool coat once evenings start cooling down. The silhouette feels elongated and powerful, which I love.

For shoes, I go for heeled ankle boots or loafers, depending on how dressy I want it. This is also a great formula for dinners, date nights, or even fashion events where you want to look on-trend but still transitional.

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Formula 7: Shorts + Button-Up Shirt + Knee Boots

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This last one might surprise you, but hear me out. Tailored shorts can absolutely work in early fall if styled right. I love pairing structured shorts (like a wool-blend or cotton tailored pair) with a crisp button-up shirt and then grounding the look with knee-high boots.

It’s such a fashion-girl outfit — playful but practical. Throw on an oversized blazer or trench, and suddenly it’s very street-style chic.

If you’re someone who loves experimenting, this is your chance. Add gold jewelry, a structured bag, and maybe even a felt fedora, and you’ll look like you’re straight out of a fashion week street-style roundup.

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If you are on the journey to building, developing and mastering your personal style, which would be really helpful when you're curating your own outfits this fall, make sure you check out a post I did that would help you with that .

👉 How to Build a Killer Personal Style on a Budget

Final Thoughts: Making Transitional Dressing Effortless

The biggest lesson I’ve learned about dressing for late summer and early fall is that it doesn’t have to mean buying a whole new wardrobe. It’s about being creative with what you already own, mixing textures, and playing with layers.

Each of these formulas has become part of my personal fall 2025 capsule wardrobe, and honestly, they’ve made my mornings so much easier. When I know I can grab a slip dress and blazer, or a sundress and chunky sweater, it takes the guesswork out of transitional dressing.

If you’ve been struggling with what to wear in September, I hope these ideas spark some inspiration for you. And remember — fashion should feel fun and personal. Take these formulas and make them your own.

 Which of these transitional outfit ideas will you be trying first? Drop it in the comments below — I’d love to know!