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Gap continues to kill it, leaning into its roots in classic, casual American style. Their latest collections are packed with elevated basics that make up the foundation of a chic and effortless wardrobe.
When I was a kid, Gap was the epitome of cool. Remember their glossy navy drawstring bag? If you had one slung over your shoulder, you knew you were feeling yourself. Their stores were filled with the best denim, cozy sweatshirts, and that perfectly effortless aesthetic we all wanted to embody.
Now, with modern fashion drawing heavy inspiration from the ’90s, this resurgence feels especially relevant. That era was built on timeless style—relaxed, practical, and undeniably cool. There’s an ease to it, a casual elegance that feels both modern and refreshingly unfussy.
And right now, it’s the perfect time to shop—Gap’s Friends & Family Event is happening, with 40% off almost everything. That means you can refresh your wardrobe with high-quality basics at an even better price.
Below, I’ve rounded up my top picks from Gap’s newest arrivals—simple, well-cut silhouettes in a range of neutrals, with a few pops of color for added interest. Their inclusive sizing is another standout feature, offering regular, tall, and petite options from XXS to XXL (which translates to a 20/22).
Looking for more wardrobe recommendations? Check out my guide to the Best Clothing for Women Over 40.
What to Buy at Gap
Icon Trench Coat
Gap’s Icon Trench is a timeless, full-length coat with a classic silhouette. At 5’10”, I find the regular fit (rather than tall) works best for me. If you’re on the petite side, don’t shy away from a longer trench—you can absolutely pull it off! The key is to have it hemmed to a length that flatters your proportions, which is a simple and affordable alteration.
With Friends & Family savings, this coat comes in at around $100—an incredible price for a versatile staple that will stand the test of time. Available in regular and tall, sizes XXS – XXL.
Icon Trench Coat
Gap
$168 + 40% OffCropped UltraSoft Denim Trench Jacket
For a fun and unexpected twist, I love Gap’s Cropped Denim Trench Jacket—a true statement piece and outfit maker that stands out from the ordinary. Available in regular, tall, and petite (XXS – XXL), it’s well priced around $100 after savings.
Style it effortlessly with anything from darker-wash jeans for a chic denim-on-denim look to classic tan or black pants. Just add a simple white tee, and you’re set!
Cropped UltraSoft Denim Trench Jacket
Gap
$168 + 40% OffOrganic Cotton VintageSoft T-Shirt
It’s no secret that at my core, I’m a jeans and tee shirt kind of girl—it’s the foundation of most of my outfits. From there, I’ll add a layer, whether it’s a nubby sweater or a blazer. I’m also very clear on my spending threshold for a basic tee—$50 is my absolute max for something that makes me feel like the cool girl I’m not.
Enter Gap’s Organic Cotton Vintage Soft T-Shirt—a fantastic find at $29.95, but when it goes on sale for around $17, that’s when I stock up for the season. Available in regular, tall, and petite (XXS – XXL) in a range of colors, but I keep it classic with white, black, and black-and-white stripes.
Organic Cotton VintageSoft T-Shirt
Gap
$29.95 + 40% OffLinen-Blend Maxi Dress
Gap’s Linen-Blend Maxi Dress is a timeless summer staple—light, effortless, and perfect for hot days and breezy nights. Available in black and a gorgeous, true summer red, it’s selling fast, but it’s worth sharing in case you’re in need of a chic new dress for spring break or any summer event.
Style it with strappy sandals, and don’t forget to bring along a denim jacket—just in case you end up seated under the arctic blast of indoor air conditioning. Available in XXS – XL, but sizes are going quickly since it’s on sale for about $60.
Linen-Blend Maxi Dress
Gap
$98 + 40% OffUltraSoft Denim Maxi Dress
Another dress that’s selling fast but worth mentioning is the UltraSoft Denim Maxi Dress—and let me tell you, I am SO over seeing the same dress on repeat for what feels like six seasons. But this? This is different.
I love everything about it—the flattering shape, dark denim wash, zipper detail, and front slit—yes to all of it. If it were still available in my size, I’d have scooped it up immediately.
If you have curves, this silhouette should hug them in all the right places—definitely worth a try if your size is still in stock. Available in regular and tall (XXS – XXL), but sizes are very limited. On sale now for $65!
UltraSoft Denim Maxi Dress
Gap
$108 + 40% Off100% Cotton Relaxed Sweater
ChatGPT said:
I’ve been making a real effort to prioritize natural fibers and fabrics, and while they can be tricky to find, they’re not impossible. Case in point: this 100% Cotton Relaxed Sweater—the perfect lightweight layer for spring that I’ll also throw on during cool summer nights at the beach.
At just under $50 on sale, it’s a great buy and comes in a range of colors. I, of course, went with the natural and the stripe (obviously). Available in regular, petite, and tall (XXS – XXL).
100% Cotton Relaxed Sweater
Gap
$79.95 + 40% Off100% Linen Oversized Shirt
Another great natural fiber option at an amazing price is Gap’s 100% Linen Oversized Shirt. This is the ultimate breezy, effortless piece—perfect for pairing with lightweight summer jeans, or shorts.
It comes in several beautiful colors, but I opted for this trend-right butter yellow, which looks stunning with white and light-wash denim. Available in Regular, Tall, and Petite (XXS – XXL) for $50.
100% Linen Oversized Shirt
Gap
$79.95 + 40% OffDenim Stripe Big Shirt
Another great button-up option is Gap’s Denim Stripe Big Shirt—a fresh take on the classic chambray shirt. The subtle stripe adds a touch of texture and depth, giving it a more elevated feel while still being an easy, throw-on-and-go piece.
I love this styled with slim-lined jeans and either loafers or low-profile sneakers for an effortlessly polished look. Available in Regular, Tall, and Petite (XXS – XXL), and currently on sale for around $40.
Denim Stripe Big Shirt
Gap
$69.95 + 40% OffHigh Rise Stride Wide-Leg Ankle Jeans
A Gap roundup wouldn’t be complete without a great pair of jeans! I’m loving these Wide-Leg Ankle Jeans, which are perfectly priced at just under $50—a fair price for denim that’s ideal for spring and summer.
Available in Regular, Tall, and Petite, sizes 24–35, with short, regular, and long inseams. I went with white for summer, but there are plenty of other color options to choose from.
When styling wide-leg jeans, most of us will want to pair them with a top that skims the body to create balance. And I positively loathe the shoe choice in the featured image—a black ballet flat feels way too harsh. Instead, opt for a sandal with a small heel (height works well with a wide leg) or a mesh flat, like these from Dolce Vita, for a lighter, more effortless feel.
High Rise Stride Wide-Leg Ankle Jeans
Gap
$79.95 + 40% OffLinen-Blend Longline Vest and Trousers
Finally, I’ve had my eye on the summer vest and trouser set trend for a while, and I think this is the one I’m going with. It’s effortless yet polished—a chic alternative to a classic top-and-jeans combo.
Both pieces are a lightweight linen blend and are sold separately, giving you the flexibility to mix and match.
The trousers come in both low-rise and high-rise options—choose whichever fits you best. Available in Regular, Tall, and Petite, sizes 00 – 20.
The vest is available in Regular, Tall, and Petite (XXS – XXL).
Linen-Blend Longline Vest and Trousers
$79.95 + 40% Off
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