The Under-$300 Edit

With ’90s minimalism and utilitarian foundation pieces top of mind for fall, it’s no surprise we’re seeing the return of the carpenter pant. Take styling cues the J.Crew way by teaming a layered pullover with tonal khaki painter pants—a power pairing inspired by the brand’s archive yet perfectly in step with what we want to wear right now—the definition of relaxed elegance.

Channel the season’s modern-prep mood with one of the aesthetic’s most iconic patterns. Reformation’s argyle cardigan feels fresh paired with J.Crew’s distressed faux-leather miniskirt—a take on prep standbys with just the right edge—it’s uptown funk done right. Finish with kitten-heeled pumps, knee-high boots, or ballet flats, depending on your mood.

Your 9-to-5 wardrobe doesn’t have to fall flat when the temperatures drop. This sequined pencil skirt from Mango makes all kinds of workwear combinations shimmer, whether paired with a silky button-down or a textured cardigan. Top it off with brown leather loafers and a stylish work tote for those days at the office when you’re in need of a pick-me-up—or to make your lengthy commute a little more bearable.

Segue into the weekend and cooler weather with J.Crew’s broken-in barn jacket that’s a bolder variation of traditionally toned-down chore coats. The only lingering hint of summer? These breezy poplin pants from Leset, styled with a classic white T-shirt and some streamlined sneakers for a preppy-meets-modern vibe.

In anticipation of fall, manifest the season with an autumnal color palette. Dôen’s deep red dress will feel like a breath of cold, crisp air during summer’s last heat waves and usher you through the end of A/C weather with its long sleeves. Consider layering it with a cozy cardigan, barn jacket, or trench when the timing is right. For another color wheel complement, wear it with richly hued mary jane slippers from Flabelus.

One of the savviest transitional layering pieces is a long-sleeved maxi. Take some cues from this Banana Republic knit in rich chocolate brown, which can be paired with metallic sandals on the last summer Friday of the year, or swapped for knee-high boots in the weeks to come for a contemporary, bohemian feel.

Keep the prep-forward influences going with Breton stripes and nautical references. Sea’s bubble-hem dress is the perfect in-between option for right now, with long sleeves and a mini length, ideal for transitional weather. Simply add Sperry’s signature boat shoes and a canvas bag to finish things off, and you’ll be riding the high seas (or at least that morning commute) in serious style.

We all know the power of a good LBD—but we’re leaning towards lengthier versions as summer comes to a close. Faithfull’s black maxi dress can go from your morning cornetto to evening tiramisu in a flash. We love the idea of it paired with a whimsical sandal, adorned with pearlescent beads, to illustrate the day-to-night idea. For cooler nights, add a boxy jacket or effortless cardigan as an easy topper.

Transitioning your summer workwear wardrobe to greet the change in seasons means choosing easy basics with an added dose of elevated flair. Faithfull’s wide-leg, pinstripe pants are made from a cotton twill, still sensible enough for those lingering hot days that turn into crisp nights. Pair them with a classic, white button-down from Banana Republic, for instant outfit perfection. Complete the look with a simple shoe, then add a leather tote bag.

There are still plenty of warm days on the horizon, but if you’re looking to transition your wardrobe to match autumn’s mood, incorporating menswear motifs—in warm weather-approved fabrics—is the easiest way. Posse’s striped set will give you the feel of fall suiting, while still being completely wearable during those end-of-summer heatwaves. Accessorize with sandals while you still can, then slip into loafers as the temperatures start to drop. You can always add light layers—a barn jacket, cropped trench, or oversized blazer will complement this set perfectly.

Voluminous balloon pants are taking over the streets, inspired by the bohemian shapes that were presented on the runways for fall/winter 2025. If you are wondering how to wear them—the answer is simple: style them with an equally airy blouse for effortless fluidity. A minimalist pendant necklace and lace-up sandals now (you can swap for a clean ballet flat later in the season) are your finishing touches.

Get ready for the last few weeks of summer with Sara Cristina’s playful mesh set. Whether you’re finally taking that vacation and need a poolside ensemble to go from sunbathing to sunset cocktails, or you’re looking for lightweight and packable pieces for an upcoming beach weekend, this mix and match pairing is sure to play double duty in your wardrobe.

There’s still plenty of time to enjoy summer’s best dresses and Hill House’s latest plaid print feels right at home for New England-inspired styling. Add a basket bag, fisherman sandals, and a cable knit sweater for around your shoulder—and don’t forget the lobster roll.

Lean into prints for the last weeks of August, when the temperatures are still blazing, and less is truly more. This slinky dress from Zara in a graphic zebra pattern feels sultry yet still simple, perfect for nights out when paired with Massimo Dutti’s red wrap sandal. Add a bold gold earring and you’re good to go.

Transition summer’s slinky slip skirt into fall’s cooler days with a sheer, long-sleeved top from Deiji Studios. It complements the texture (and butter yellow hue!) of Reformation’s lace-trimmed satin option perfectly. We recommend pairing with everything from leather flip-flops to soft ballet flats, or even a sleek loafer, depending on your mood.