MomSkoop
September brings that perfect in-between weather where summer still lingers but fall is definitely in the air. While many are rushing to break out boots, those of us who love our flat sandals aren’t quite ready to pack them away. The good news? You can absolutely rock your favorite flat sandals well into September with the right outfit pairings. Here are five stylish ways to keep your toes free while looking seasonally appropriate.
1. Midi Skirt Magic
A flowy midi skirt paired with flat sandals creates that perfect balance between comfort and style. The longer hemline offers just enough warmth for cooler September mornings while still feeling breezy enough for afternoon sunshine.
Try a pleated version in rust, olive, or navy to capture those early fall vibes. Add a simple tucked-in t-shirt or light sweater, and you’ve got an outfit that transitions beautifully from summer to fall.
For extra style points, throw on a denim jacket when temperatures dip in the evening. This combination works for everything from office days to weekend brunches!
2. Cropped Jeans Combo
Raw-edge cropped jeans practically beg to be paired with flat sandals! This winning combination shows just the right amount of ankle while giving your September outfits a relaxed, effortless vibe.
Straight-leg or wide-leg crops work beautifully here – the key is finding a length that hits right above your ankle bone. Dark wash denim feels more fall-appropriate while still maintaining that casual coolness.
Top the look with an oversized button-down or light sweater. Roll the sleeves for that perfectly undone look that says “I’m not trying too hard” while still looking completely put-together.
3. Maxi Dress Moments
Remember that floral maxi dress you wore all summer? Don’t store it away just yet! Maxi dresses and flat sandals are September’s power couple, especially when you add a few strategic layers.
Choose dresses in deeper tones or with smaller prints that feel less beachy and more transitional. A lightweight cardigan or denim jacket instantly transforms the look from pure summer to early fall perfection.
Gold jewelry and maybe a felt hat complete this boho-inspired ensemble. The best part? This outfit keeps you comfortable through unpredictable temperature swings that define September days.
4. Tailored Shorts Twist
Not ready to give up shorts? Tailored versions in heavier fabrics like tweed, linen blends, or lightweight wool make perfect September companions for your flat sandals.
The structured silhouette elevates basic sandals instantly. Pair with a tucked-in blouse or thin sweater for an outfit that works for casual offices or weekend adventures alike.
The trick to making this look seasonally appropriate is choosing shorts in fall colors like camel, burgundy, or forest green. This unexpected combination feels fresh and practical for those September days when temperatures still climb into the 70s.
5. Jumpsuit Joy
A jumpsuit might be the most underrated sandal partner for September transitional dressing. This one-and-done outfit solution pairs beautifully with flat sandals for an effortlessly chic look that requires minimal planning.
Linen or cotton jumpsuits in solid colors work year-round. For September, opt for deeper hues or add a light jacket to make the outfit feel more seasonally appropriate.
The ankle-baring nature of most jumpsuits creates the perfect spotlight for your favorite flat sandals. This combination gives you that coveted relaxed elegance that works for everything from farmers’ markets to casual Friday at the office.
6. Linen Pant Perfection
Breezy linen pants create the ultimate balance between summer comfort and fall sophistication when paired with flat sandals. The lightweight fabric keeps you cool during warm September days while the full-length coverage acknowledges autumn’s approach.
Choose neutral-toned pants in beige, olive, or rust to capture the seasonal transition. Add a fitted tank top or light sweater depending on the temperature. For cooler evenings, layer with an oversized cardigan or light denim jacket.
This combination works beautifully for everything from casual office settings to weekend brunches. The relaxed-yet-polished vibe strikes that perfect September balance!
7. Denim Skirt Revival
Remember the denim skirt you lived in all summer? Don’t store it away just yet! Paired with flat sandals, this combo transitions perfectly into September with a few smart adjustments.
Swap your summer tees for lightweight sweaters or button-downs in autumn hues like burgundy, mustard, or forest green. The contrast between casual denim and more structured tops creates visual interest while keeping you comfortable.
A mid-length denim skirt works best for this time of year, offering more coverage as temperatures gradually drop. Add a leather or suede crossbody bag to complete this effortlessly cool look that works for campus, coffee dates, or casual Fridays.
8. Wide-Leg Trouser Elegance
Who says flat sandals can’t look sophisticated? Pairing them with wide-leg trousers creates an unexpectedly chic September outfit that’s both comfortable and elegant. The contrast between structured pants and casual footwear strikes the perfect balance.
High-waisted styles in lightweight fabrics like crepe or cotton-blend work best. Colors like navy, charcoal, or camel transition beautifully into fall while maintaining versatility. Top with a tucked-in blouse or fitted tee to highlight your waistline.
This combination elevates your flat sandals instantly, making them appropriate for semi-formal settings or workplaces with flexible dress codes. Add a structured blazer for cooler days or important meetings.
9. Layered Mini Dress Approach
Summer mini dresses get a September upgrade when thoughtfully layered! The secret lies in adding just enough warmth without overwhelming your breezy dress and flat sandals combo.
Start with your favorite mini dress – floral patterns or solid jewel tones work wonderfully for this transitional period. Add a lightweight denim jacket, cropped cardigan, or even a thin turtleneck underneath for instant fall vibes. Black or brown flat sandals ground the look while maintaining summer’s ease.
Finish with tights if temperatures dip or keep legs bare on warmer days. This versatile approach lets you adjust layers throughout the day as September’s unpredictable weather changes, making it perfect for weekend adventures or casual gatherings.
10. Slouchy Sweater Balance
The slouchy sweater and flat sandals pairing might seem contradictory, but that’s exactly what makes it so perfect for September’s in-between weather! This unexpected combination balances cozy top layers with breezy footwear.
Opt for lightweight knits in fall colors like pumpkin, burgundy, or camel. Pair with shorts on warmer days or leggings/skinny jeans when temperatures drop. The oversized silhouette creates a relaxed vibe that works perfectly with the casual nature of flat sandals.
For added style points, choose sandals with interesting details like metallic accents or unique straps. This outfit works wonderfully for weekend errands, casual gatherings, or those work-from-home days when you might step out for coffee or lunch.