Outfits You’ll Wear on Repeat: Late Summer to Early Fall 🍂
I used to dread this time of year… when it’s too hot for sweaters but too cool for sundresses. Add in my midlife midsize belly, and transitional outfits felt impossible. Do I dress for the heat? The chill? Or the fact that my jeans sometimes have a mind of their own? 😅
But over the years, I’ve found that the key to late-summer-to-fall dressing isn’t about hiding anything—it’s about contouring, balancing, and feeling comfortable enough to actually live your life in the clothes.
So today I’m sharing five belly-friendly, midlife-approved outfits from J.Crew Factory that will carry you through those tricky in-between weeks. Think: school drop-off, coffee runs, casual dinners, or even that first pumpkin spice latte stop. These are outfits you’ll reach for on repeat, promise.
✨ See these looks in action! Watch my full Instagram Reel for belly-friendly, late-summer-to-early-fall outfit inspo: [Instagram Reel] 🍂💛
Off-White Wide Leg Jeans + Navy Puff Sleeve Top
✨ Where to Wear: Weekend errands, dinner with friends
Wide leg jeans are my best-kept secret for balancing proportions and giving that “contoured but comfy” vibe. Pairing them with a navy puff sleeve top keeps it polished but playful—structured enough to feel styled, but not clingy around the belly.
Navy Linen-Blend Button-Front Mini Dress
✨ Where to Wear: Brunch, date night, casual work days
Linen is magic for transitional weather—it breathes in the heat, layers easily when the sun goes down, and doesn’t scream “summer-only.” A button-front mini dress gives just enough shape without clinging, and with sandals or booties? She works overtime.
Gingham Button-Down + White Shorts
✨ Where to Wear: Sporting events, casual Fridays, mom duty
This one’s for the late summer days when you’re still sweating by 2 p.m. 🙋♀️ The gingham button-down gives structure, while the white shorts keep it fresh. Front tuck it to contour the belly (instead of fighting it) and throw on sneakers for an easy-go look.
✨ Where to Wear: Dinner out, casual Fridays, wine night
These jeans are a closet hero: structured enough for fall, but cropped so you’re not overheating in August. Add a sage puff sleeve top for a soft, feminine contrast. This combo just gets it—comfortable, flattering, and forgiving on the belly.
Navy Sweater Over the Shoulders + White Tank + Sage Flare Pants
✨ Where to Wear: Evening walks, casual coffee, transitional work days
This is the ultimate late-summer-to-fall layering trick. Toss a sweater over your shoulders (hello, instant chic) and keep a breezy tank underneath for when the temps rise. It’s belly-friendly layering at its finest—contoured without adding bulk.
Why These Work for Midlife & Midsize
The common thread? These outfits don’t try to hide the belly. Instead, they balance and contour it so you feel confident in any setting. Puff sleeves, wide legs, layering tricks—all little styling moves that keep things flattering while staying comfortable.
And honestly? That’s what midlife fashion should be about. Not chasing trends, not sweating through your clothes—just wearable outfits you’ll reach for again and again.
So if you’re standing in front of your closet this week thinking: “It’s too hot for fall, but too chilly for summer”—you’re not alone. These are the exact transitional outfits that make me feel put-together without overthinking it.
👑"Helping you look good, feel good!" - Lindsey Denver
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