We’ve officially entered the season of cool mornings, warm afternoons, and the eternal question: what do I wear today? In 7 Transitional Outfits to Wear from Summer into Fall, I’m sharing the exact formulas I reach for when I want to look polished in August and equally put-together in October. Yep, it’s that tricky time of year when your closet feels like it’s having an identity crisis. But I promise that’s where transitional dressing comes in. It’s about making the most of what you already own, adding a few smart layers, and creating outfits that work now and in the weeks ahead.
Today, I’m sharing 7 transitional outfits that carry you seamlessly from the tail end of summer into the crisp early days of fall. Each look has two versions: Wear It Now for the heat and Wear It Later for cooler temps.
1. Gingham Midi Shirtdress
Beth’s Style Tip: A gingham shirtdress is one of those timeless pieces that works for every age and every season. Keep the accessories light in summer and richer in tone for fall.
Wear It Now: Pair a gingham shirtdress with espadrilles, a raffia belt, and a straw tote. Roll the sleeves and unbutton the collar for a breezy summer vibe.
Wear It Later: Layer with a cropped denim jacket, swap sandals for ankle boots, and trade the straw bag for a structured leather handbag.
2. Gray Sleeveless Cashmere Sweater + White Denim
Beth’s Style Tip: Gray and white is a chic alternative to black and white — soft, modern, and endlessly versatile.
Wear It Now: Style a sleeveless cashmere sweater with white denim, espadrilles, a canvas bag, and gold jewelry. Crisp, clean, and perfect for warm days.
Wear It Later: Add a camel trench or gray sweater jacket, swap in loafers or flats, and finish with a leather bag for fall polish.
3. Ralph Lauren Ricky Pant
Beth’s Style Tip: Wide-leg trousers like the Ricky Pant give instant polish. Show off the waistline with a full tuck to elongate your legs.
Wear It Now: A white tee, lightweight blazer and linen mules make this look breezy but elevated.
Wear It Later: Add the same gray cashmere sweater from Look #2 or a knit turtleneck. Layer with a blazer and add a silk scarf for a full fall moment.
4. Black Sleeveless Midi Dress
Beth’s Style Tip: A black midi dress is the definition of year-round dressing. Think of it as your blank canvas for endless layering possibilities.
Related Post: The Chic Petite Dress
Wear It Now: Wear solo with sandals, a raffia tote, and a straw hat.
Wear It Later: Add a cropped cardigan or plaid blazer, suede boots, and a structured handbag.
5. Navy Blazer + Luxe Basics
Beth’s Style Tip: A navy blazer with gold buttons is a forever piece. It instantly upgrades even the simplest outfit.
Related Post: How to Style a Blazer
Wear It Now: Layer over a white tee and white jeans or a slip skirt for a light, fresh look.
Wear It Later: Switch to a striped tee, dark denim, and loafers.
- Navy Tweed Blazer
- Striped Tee
- Dark Rinse Denim
- Gold Teardrop Earrings
- Suede Slingbacks
- Similar Leather Handbag
6. Navy Slip Skirt + Cardigan
Beth’s Style Tip: Slip skirts are seasonless — the trick is in the texture. Keep it light for summer and layer in cozy knits for fall.
Wear It Now: Pair with a cotton cardigan and canvas espadrilles for a breezy, feminine look.
Wear It Later: Swap in a cashmere cardigan, metallic slingbacks, and a metallic handbag for date night.
7. Ralph Lauren Denim Jumpsuit
Beth’s Style Tip: A denim jumpsuit is a one-and-done outfit that still looks intentional. Belt it for shape or leave it relaxed — both work beautifully.
Wear It Now: Roll the sleeves, add suede sandals, and keep accessories minimal for effortless style.
Wear It Later: Layer with a trench or plaid blazer, add suede loafers or boots, and finish with statement earrings and a suede hobo handbag.
FAQs – Transitional Outfits for Summer to Fall
Can I wear white denim after Labor Day?
Absolutely! Just pair it with richer textures and fall tones to ground the look.
How do I layer without overheating?
Opt for sleeveless or lightweight base layers, then add removable toppers like blazers or cardigans.
What’s the easiest way to make summer dresses work for fall?
Layer with a jacket or cardigan, swap in closed-toe shoes, and add fall accessories like scarves or leather handbags.
Are slip skirts still in style for 2025?
Yes — slip skirts are timeless. Just adjust your fabrics and footwear to match the season.
Final Thoughts
Transitional dressing doesn’t require a whole new wardrobe — just a little creativity. With these seven outfit formulas, you can glide from the heat of August to the crispness of October without missing a style beat.
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About The Author
That brown checked dress was a fail it makes you look so frumpy! Sorry
Thanks for the candid note—style is personal, so it’s okay if this isn’t for you. I define ‘frumpy’ as collapsed proportions (droopy shoulders, no waist, dragging hem). Here I kept structure—a belted waist, mid-calf hem with a slit, and a clean shoe—so it reads classic, not frumpy. If you prefer more definition, try a shorter hem, a cropped jacket, or a heel.
Loved this post how you did the outfit now and then later.
Great ideas!
Thank you! I love the “now & later” format—double duty from one piece is the goal. Try it with a slip skirt: tee + cardigan + espadrilles now; swap to cashmere cardigan + slingbacks + cami later. Which piece are you styling both ways this fall?
Great post! Very informative and helpful for using clothing already in our closets!
Thank you! That’s exactly the goal—shop your closet first, then add one smart update (a third piece, a sharper shoe, or a fresh belt) to make it feel new. What combo are you trying first? I’d love to hear what you rediscover.
You look gorgeous in all your clothing choices today. The denim jumpsuit looks like your personal best!! Love that look!
Also, you show how adding a beautiful silk scarf can elevate the total style.
Thank you for so many style options.
Thanks a million! Love that you noticed the scarf—triangle fold, half-knot, done. I’ll share a few budget-friendly silk options this week.
This was great – perfect timing. I’ve selected three new pieces from your post, I need a bit less expensive striped tee to go with the navy blazer and I will have created several summer to fall outfits. Yay!
I would like your professional opinion. I love Quince, but many of their shirts/jackets are oversized (other brands do this as well) I am fairly small built, but not considered a petite in sizing, and worry I’ll just look sloppy. Should I order a size down- is there a guideline on how oversized is too much? Thank you Beth.
Great question. Oversized should skim—never swamp. Quick fit guide:
• Shoulders: seam should land at (or within ¼–½”) of your shoulder edge.
• Bust ease: about 2–4″ of extra room; if you can pinch more than ~1½” per side seam, it’s too big.
• Length: shirts mid-hip; blazers covering ½–⅔ of your seat. If the hem eats your frame, size down.
• Sleeves: end at wrist bone; rolling once or twice adds structure.
If a brand labels it “oversized,” try one size down (keep the shoulder/lapel clean). You can also order regular and petite in jackets—the petite’s shorter body/sleeve can flatter even if you’re not a petite overall. Balance the volume with slimmer bottoms, a half-tuck, or a belt. And remember: a quick tailor nip at the waist or sleeve makes “relaxed” look intentional.
Thank you! This is very helpful.
Thanks for the nice post, guide to dressing up.
What is link for the blue and white striped dress you have on in the opening picture for today? I couldn’t find a link in the text. Thanks!
Wonderful post. Thank you. I saw the brown checked dress on a person in a hospital office a week or so ago, and it looked wonderful. She had paired it with accessories similar to the way you styled it.