I Spent Hours Trying on Gap’s Entire Sale Section IRL, and These 7 Travel Outfits Made the Cut—From $15

When I’m shopping for travel outfits, Gap is one of those tried-and-true stops I always circle back to—the racks are filled with mix-and-match staples that somehow work for every trip and every season. So, when I realized the brand’s Friends & Family Sale was offering 40 percent off sitewide and ending in a few days, I did what any rational person would do: raced to my local Gap to see what was left before the good stuff vanished (as it always does). Spoiler alert: it was absolutely worth the trek.

In true travel writer fashion, I approached the fitting room like field research—pulling travel clothes like matching sets, chunky cardigans, and sweatpant jeans. The fall lineup was full of rich textures (think cable knit sweaters, suede ballet flats, and denim puffer jackets) that made it way too easy to justify a few extra “add to carts.” 

After some tough narrowing down, I landed on seven Gap fall outfits that check every box: cozy, versatile, and right on trend for fall. Below, you’ll find every look I tried on in-store—just don’t wait too long to shop, because these pieces are selling fast.

Best Overall Gap Deals

Outfit 1

This is the ideal airport outfit—or honestly, your cozy Sunday errand uniform. The Cashsoft zip-up hoodie and matching boot sweater pants feel like cashmere but ring in under $50 during the fall Gap sale. The oatmeal color I tried on is nearly sold out, but the black version is still in stock—timeless, versatile, and seasonless. I love that the hoodie works as a sweater when zipped, or you can wear it open with a tank or tee underneath. The pants have a flattering bootcut shape and a clean, elasticized waistband (no drawstring!), so they read more “effortlessly elevated” than “just rolled out of bed.” 

Cashsoft Sweater Zip Hoodie

Cashsoft Boot Sweater Pants

Outfit 2 

For those who prefer a little more structure at the airport, this look hits that sweet spot between tailored and travel-ready. The viral sweatpant jeans look exactly like denim but are secretly a soft cotton-blend terry with a pull-on waistband—a true win for long flights. I paired them with Gap’s Vintage Soft T-shirt, a capsule wardrobe essential that somehow feels lived-in from the start, and layered on my favorite fall piece right now: the Icon Trench Coat. 

This trench coat instantly sharpens any outfit and doubles as the perfect travel layer: wear it open now or belted once you’re en route and saving space in your suitcase. This entire combo feels so effortless yet composed, the kind of outfit that looks intentional even after a red-eye. Pieces are selling out fast with the Friends & Family sale ending soon, so consider this your sign to check out while you still can.

Heavyweight Easy Baggy Sweatpant Jeans

Icon Trench Coat

Outfit 3

Chocolate brown is the color fashion people can’t stop wearing this fall—and I’m fully on board. There’s something about a tonal brown outfit that feels rich and quietly chic, especially when it’s this easy to style. I paired Gap’s soft brown sweater with matching denim and suede ballet flats for a clean monochromatic look that feels modern and warm at once. But, these pieces are limitless—you can easily swap in classic blue jeans for a more relaxed vibe, or layer on the Icon Trench from earlier to add depth. It’s the kind of outfit that makes you look instantly pulled together, even if you got dressed in five minutes. 

CashSoft Stretch Lantern-sleeve Crop Sweater

Vegan Suede Ballet Flats

Outfit 4

I already own this cable-knit set in gray, so spotting the new winter white version felt like a no-brainer addition to my wardrobe. The fabric is ultra-soft and cozy—one of those rare finds that feels like loungewear but looks styled and intentional. A textured cable pattern and slightly cropped hem make the sweater flattering on its own or paired with the matching pants. 

The sweater also doubles as a standalone top: try it with wide-leg jeans and boots for a polished, après-airport outfit, or keep things relaxed with the matching pants and Uggs. To top it off, I added the denim puffer jacket, one of my favorite discoveries from this try-on. The dark blue hue pops against the winter white, the adjustable drawstrings let you shape the fit, and the warmth-to-weight ratio makes it ideal for cold-weather travel. 

CashSoft Cable-knit Crewneck Sweater

CashSoft Cable-knit Sweater Pants

Outfit 5

A chunky cardigan is always one of my fall essentials, and this one nails that balance of cozy and polished. The navy hue feels fresh: a softer alternative to black that still goes with everything. I styled it simply with mid-wash jeans and a white tee, but it also works buttoned-up as a sweater or paired with tan trousers for a more elevated, office-ready take. Navy and brown are one of my favorite fall color pairings, so don’t be afraid to mix the two. The jeans, by the way, are a total capsule find: a true mid-wash that works with everything in your closet, from loafers and a blazer to sneakers and a trench. It’s the kind of outfit you’ll rewear weekly—especially with these staples marked down during the Friends & Family Sale.

Cashsoft Oversized Chunky Cardigan 

Organic Cotton VintageSoft T-shirt

Outfit 6

The cow-print ballet flats stole my heart the moment I tried them on—proof that a single standout accessory can transform your entire outfit. The neutral tan and brown tones keep them surprisingly wearable, and they’re down to just $42 right now with the sale. I styled them with the oversized faux-leather bomber in a rich chocolate brown, which is another must-grab piece while it’s still in stock. The gold hardware and slouchy fit give it that effortlessly cool edge that makes any outfit feel styled. Underneath, I wore a simple ivory cardigan and dark-wash jeans—an easy base that lets the accessories shine. 

Oversized Vegan Leather Jacket

CashSoft Crop Cardigan

Outfit 7

Barrel jeans are everywhere right now—and for good reason. This pair fit me like a glove and nailed that structured-but-relaxed shape that somehow flatters every body type. The curved leg and tapered ankle create a subtle elongating effect, giving the illusion of longer legs while still feeling easy and comfortable to move in. I styled mine simply with a black cardigan, which lets the unique silhouette take center stage, but they’d look just as good with a tucked-in tee and blazer for a more polished take. A black suede belt would finish the look perfectly—a small detail that adds texture and ties everything together. 

High-rise Horseshoe Barrel Jeans

Suede Belt

Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.