Madewell has always been one of my favorite places to shop for pieces that feel both timeless yet trend-forward. So, when I spotted the brand’s massive fall sale, with an extra 50 percent off sale styles using code “LONGWEEKEND,” I knew my wallet was in trouble (in the best way). The discounts are too good to scroll past—think wide-leg jeans for just $30, tailored trousers marked down a whopping 83 percent, and more travel clothes that make packing for any fall trip a breeze. 

From midi dresses to comfy mules and lightweight cardigans, the sale section is filled with elevated staples you’ll want to live in all season long. Prices start at just $20, but with deals this good, sizes are going fast. Trust me, you’ll want to shop before the long weekend (and these markdowns) come to an end. 

Best Overall Madewell Fall Sale Finds

Denim Scoopneck Midi Dress

This 100 percent cotton denim midi dress is fall’s answer to effortless dressing. It’s light enough to wear solo while temps are still in the 60s and 70s, but layers beautifully under a trench or blazer once it cools down. With pockets (always a win) and a versatile silhouette, it’s an easy pick for travel—just swap sneakers for boots or loafers to instantly change the vibe.

The Slouchy Straight Pants

Now a shocking 83 percent off, these straight-leg pants are the pair I practically live in. They strike that perfect balance of relaxed and refined—soft and comfy enough for a long flight, yet structured enough to wear straight to dinner. At just $20, they’re a total steal and endlessly versatile: pair them with a tee and sneakers for travel days or a sweater and ballet flats for a sophisticated fall outfit.

The Greta Ballet Flat Mule

I love a good mule because you get the elegance of a ballet flat without that dreaded heel rubbing (truly a game changer). This studded leather pair adds a subtle pop to any outfit—whether you’re in jeans, trousers, or something dressier. Plus, the brand’s Cloudlift Lite padding makes every step feel cushy and supported. At 61 percent off, these are the kind of shoes you’ll find yourself slipping on every single day.

Ribbed Polo Sweater

The polo sweater trend isn’t going anywhere, and this one nails that preppy-yet-polished vibe. The oversized buttons give it a little something extra, and the ribbed knit feels soft but lightweight—perfect for layering under a coat or over a tee. Wear it to the office, on a date night, or for a travel day when you want to look pulled together without trying too hard. Even better? It’s only $40 right now.

Superwide-leg Jeans

These jeans are the fall denim steal—just $30 for a pair that feels designer-level. The dark blue wash complements every autumn shade, from chocolate brown to camel, and the wide-leg cut is both flattering and on-trend. Inspired by ’90s silhouettes, they’re easy to dress up or down, and they’re an absolute must if you love that effortless, cool-girl travel uniform.

Smocked Long-sleeve Top

This top turns a basic long sleeve into something special with its voluminous puff sleeves and smocked cuffs. The lightweight cotton jersey keeps it breezy and comfortable, so it’s ideal for travel or everyday wear. Style this blouse with trousers and a suede belt like the model—or dark denim and boots for a chic fall look. And at just $25 right now, it’s a no-brainer addition to your cart.

Utility Wide-leg Trousers

These wide-leg pants are where comfort meets cool. They mix the practicality of a utility pant with the sophistication of a trouser, featuring cargo-style pockets and a casual, lived-in feel. They’re dressy enough for brunch or the office but comfy enough for a long-haul flight. I’d wear them exploring a new city like London or Copenhagen with sneakers and a tucked-in tee.

Pointelle-knit Cardigan Top

A lightweight cardigan is a fall essential, and this one is too good to pass up at just $23. The charcoal grey hue and textured ribbing give it that cozy-meets-chic appeal. You can wear it buttoned up as a sweater or open over a tank with a belt and Mary Janes for a complete look. It’s the perfect transitional piece for layering through the season.

Asymmetrical Ruched Midi Dress

Polka dots are back in a big way, and this romantic midi dress proves why. The asymmetrical ruching at the waist creates such a flattering shape, and it transitions effortlessly between seasons—pair it with kitten heels and a blazer for fall, boots and a faux fur coat for winter, or strappy sandals come spring. It’s one of those wear-anywhere pieces you’ll reach for all year.

The Darted Barrel-leg Jeans 

Lucky you— we just found the perfect pair of barrel jeans for just $60. The light wash makes them easy to style a million ways: go casual with a striped tee and retro sneakers, wear a button-down and loafers for the office, or pair with a sweater and trench for fall travel. The praising reviews say it all: “I needed a good [pair of] jean[s] for traveling that [were] comfortable enough to sit on the plane in, and this really did the trick while looking incredibly chic.”

Bubble Tee

The Bubble Tee has earned a top spot in my closet, because I reach for it constantly. The subtle stripes add just the right amount of pizzazz, and the bubble hem plus boat neckline give it a stylish touch. It’s super versatile—I’ll wear it with blue jeans and a brown jacket one day, then switch it up with white pants for a crisp fall whites look. It’s just $20 right now, which feels like highway robbery for how often you’ll wear it.

The Cleo Straight Jeans

The Cleo Straight Jeans are sitting high on my wish list. The denim wash is chef’s kiss, and the front pockets add a unique, elevated twist. With a high rise and straight-leg silhouette, they’re the kind of everyday jeans that work for errands, travel days, and everything in between. They’re timeless, flattering, and easy to dress up or down, no matter where you’re headed.

V-neck Cutaway Vest in Corduroy

Corduroy is having a major moment, and this vest is right on trend. The green hue is peak fall, and it looks especially good styled with the matching corduroy pants for a monochrome moment. It’s also easy to layer—throw under a blazer or trench when the temperatures drop.

The Essential Curve Crossbody Bag

I’m a fan of Madewell’s bag collection, and the Essential Curve Crossbody Bag is the standout—especially at 64 percent off. The suede finish and subtle stud detailing instantly elevate any outfit, while the warm brown tone adds a fall-ready touch. It’s roomy enough for travel essentials (it will fit an iPad, water bottle, wallet, keys, etc.) and features a secure top zipper and interior pocket for peace of mind. Plus, the adjustable strap lets you wear it crossbody or over the shoulder, depending on your day.

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

As a food and travel writer, most of my travel is work-related. That’s not to say my journeys don’t include delicious food and exciting destinations, but chances are, I’ll also attend an important work meeting, dinner, or event along the way, even in the most fun of destinations. Of course, that complicates travel, as even if I’m headed to a resort or a vineyard, I have to do so with business-appropriate attire in mind—and during the summer months, when travel is hot and sweaty, these professional clothes also need to leave me feeling cool and comfortable.

That’s a lot to ask of a lightweight dress or romper, and the key aspect for me has long been finding a few great staple pieces that can play several roles at once. Think: lightweight, hot-weather friendly clothing that can easily transition to various roles each trip, like a flowy dress that works from day to night or a matching set that can be worn together or as separate pieces. Versatility is the name of the game on work trips; I want to be prepared for wherever the itinerary may take me, but in a way that is as streamlined as possible. These business casual clothes are perfect for any type of trip, and they’ll keep you cool and comfortable all summer.

Automet Short Sleeve Business Casual Blouse

This short-sleeved summer blouse checks all the boxes: it’s comfortable, lightweight, and casual, but it is so easy to dress up when the occasion merits, making it a great transitional piece for summer business travel. “Super cute and comfortable. You can take it from the office to dinner. Breathable and lightweight,” shared an Amazon five-star reviewer.

Women’s Summer Two-piece Blazer Outfit

This sleeveless vest and pants set is an absolute steal, on sale for just $34 for both pieces. But aside from being cozy and breathable, it’s a perfect set for a meeting or lunch on a hot summer day with it flowy yet polished look. “It was perfect for a recent conference with business casual attire..pants have a zip front, elastic waist in back, and pockets, which are always great!” according to an Amazon five-star review.

PrettyGarden Women’s Summer Jumpsuit

With an elegant neck and ruching at the waist, this sleeveless one-piece jumpsuit is available in a range of colors, like a dusty pink, royal blue, and versatile beige. Wear it to segue from a meeting or business lunch into a night out. “I’m always on the lookout for outfits that are stylish, professional, and comfortable enough to wear all day…This jumpsuit checks all the boxes,” said an Amazon five-star reviewer. “The mock neck adds a touch of sophistication, while the wide-leg pants give it that breezy, effortless feel. And yes—it has pockets!”

Zattcas Short Sleeve Ribbed Midi Dress

Another great spin on a one-piece outfit that transitions well from a business lunch to exploration, this under-$40 midi dress has a round neck short-sleeve top with belt-tie waist and flowing skirt that is breathable and breezy. You’ll stay cool, even on the most intense of summer days. “I purchased it right before going on a business trip to Europe, and it was perfect,” said a five-star customer. “I like how the top and bottom are connected, so you don’t have to worry about separate items. It’s a very light material and flows nicely.”

Merokeety Sleeveless Button Dress

This cute button-down sleeveless dress screams Jackie O and is a way of looking poised and polished while still feeling cool and comfortable. “Super cute dress that looks great for work!” shared a five-star Amazon review. Made of soft viscose material, it’ll feel good on even for a long day, and the sleeveless design and slightly-flowy skirt will help beat the heat.

Dokotoo Women’s Casual Jumpsuit

This casual, fun jumpsuit couldn’t be easier to pack and is lightweight and comfortable to wear. With a loose fit and side pockets, it’ll feel cool and breezy, and the patterns keep it feeling stylish, even if wearing it feels as comfortable as your favorite pair of pajamas. Amazon shoppers love the “great fit,” saying, “I got amazing compliments on this! Great for travel, conferences, and looks great with the jacket to dress it up!”

Angerella Women High Waisted Palazzo Pants 

Cute palazzo-style high-waisted wide-legged pants that can play so many roles when traveling. These would be a dream for a travel day and can adapt well with a button-down vest (more on that soon!) for a lunch meeting, but would also work beautifully over a swimsuit at the pool later in the day. Amazon shoppers love the versatility, saying, “Love these easy breezy pants. I wore these on a five-hour flight. They are loose and comfy, with pockets, [and] they can be dressed up or down.”

Zeagoo Women’s Sleeveless Button Down Shirts

A sleeveless button-down helps you stay crisp and cool while feeling put-together and professional during summer business travel. This top comes in lots of shades, so it’s a great excuse to stock up while it’s just $20. “Perfect for the summer to dress up or dress down slacks or shorts,” said one shopper. “Comfortable and gives a neat, polished look to outfits. Would be good under a blazer for work.”

Happy Sailed Women’s Sleeveless Vest 

A button-down vest can dress up even jeans or a casual sundress to feel much more business-ready, all while staying cool and collected. Amazon shoppers call this sleeveless vest a “great style and perfect fit,” saying, “I wore it on an 80-degree day. I wasn’t too hot and the vest still gave the ‘business’ look while I wore a tank top [underneath].”

Auselily Women’s Summer Empire Waist Dress 

This breezy, flowy, smocked dress screams summer picnic but is still sophisticated enough to wear when having drinks with a client or colleague. Amazon shoppers say it is flattering and wrinkle-resistant, making it perfect to pack in your suitcase without worrying about needing an iron or steamer. “This is a really beautiful dress,” one shopper wrote. “The material is mid-weight and comfortable and wrinkle-resistant, which makes this a great dress for travel.”

Heipeiwa Two-piece Linen Vest Waistcoat

This linen-blend sleeveless suit set is the perfect travel businesswear that maintains a sophisticated look even when it’s unbearably hot outside, thanks to its linen blend material. Amazon shoppers say it’s “comfy, elegant, and versatile,” making it “perfect for work or a casual meeting.” The bonus part is that you can mix and match these pieces with the rest of your travel wardrobe for even more versatility.

Tasamo Round Neck Basic Pleated Top Cap Sleeve Curved Keyhole Back Chiffon Blouse

A great buy on a wardrobe staple at just $21, this whimsical chiffon-style blouse with a pleated neckline and cap sleeves is easy to dress up with a skirt or slacks or down with jeans or shorts. Amazon shoppers love this top for business travel, and say they get so many compliments. “I love these shirts for work and business travel,” one shopper wrote. “They fold very small, and it is easy to get the wrinkles out!” There are dozens of colors available, so you can stock up on a few to wear throughout your trip. 

Wiholl Two-piece Set for Women

This two-piece tracksuit set is comfortable enough to fly or sleep in, but throw a blazer or button-down vest over it, and it’s ready for an important Zoom call while you’re busy traveling. “The material is soft, lightweight, and perfect for warm weather. I love how cute and stylish it looks without sacrificing comfort,” reads one Amazon five-star review. You can also pair the top with a pair of slacks for a business trip, and wear the shorts for lounging around your hotel room.

Acelitt Summer Lapel Collared Dress

Casual and cool, this collared button-down V-neck dress exudes summer chill and versatility. Amazon shoppers love this dress because it’s a great “wear anywhere” look. “I really like the oversized cut and relaxed fit of this dress,” wrote one shopper. “It gives off a ‘polished,’ carefree look while being extremely comfortable, and it is the perfect length for any and all occasions.” The flowy fit makes it a summer staple while the touch of elastane in the fabric gives it a little bit of comfortable stretch.

Dokotoo Sleeveless Wide-leg Long Romper With Pockets

Lightweight, soft, and comfortable for planes or long days of activity, this sleeveless jumpsuit is easy to wear casually to hang at the beach but also to dress up for a work meeting while on the road. Amazon shoppers “love” this jumpsuit, noting that it’s easy to “dress it up with a blazer, or wear it as is,” and “it’s a versatile piece for travel and every occasion.” The wide legs will keep you cool, and it’s plenty stretchy for staying comfortable all day.

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

I write about clothes for a living, so I consider myself well-versed in the world of online sales. Whether it be J.Crew’s latest summer sale or top-rated Brooks sneakers on rare sale, the best deals are almost always on my radar—and I consider myself an expert. Needless to say, I’m a little ashamed to admit that I’ve been sleeping on one travel-friendly clothing brand that offers massive discounts: Loft. 

My colleagues have been raving about the old-school mall brand, and I decided to take a peek myself, only to find a jaw-dropping semi-annual sale. I found deals up to 69 percent off, including summer dresses, linen pants, and more vacation wardrobe staples. Take a cue from me and jump on these major savings; keep reading to discover the 12 styles worth packing for your upcoming vacations, all under $50.

Best Overall Deals

Dotted Lie Linen-blend Strappy Midi Dress

When it comes to summer vacation, no style is more essential than a breezy dress. I prefer midi or maxi silhouettes that won’t risk a wardrobe malfunction, and this linen style is ideal. It features a trendy yet unique polka dot pattern, plus a stretchy smocked bodice for maximum comfort. Plus, this dress can be worn for casual or dressier occasions with a simple change of shoes. 

Pull-on Wide-leg Linen Pants

If your summer wardrobe doesn’t include a pair of linen pants, you’re missing out. Not only is the style so comfortable on hot days, but it’s versatile enough to complement just about anything in your travel wardrobe. This pair from Loft has an elevated, wide-leg silhouette, plus an oatmeal hue that’s just as timeless. They are made of 100 percent cotton for ultimate breathability, and one reviewer even said these pants kept them “cool and comfortable” at a festival in 90-degree Fahrenheit weather.

Pull-on Linen-blend Bermuda Shorts

Bermuda shorts are one of the season’s most in-demand styles, and I love this linen version that’s as comfy as it is elevated. With a stretchy, elastic waistband and flowy silhouette, I’m willing to bet you’ll swap your uncomfortable denim shorts for this airy alternative. I’d pair it with a white blouse and heeled sandals, although it can just as easily be dressed down with a simple tank and sneakers. 

Floral Ruffle Strappy Maxi Dress

This romantic, chiffon maxi dress makes me think of cobblestone streets, rustic dinners, and seaside relaxation. Of course, it will look just as fashionable as you enjoy summer at home, too. The ruffled detailing and fitted waist create an hourglass silhouette, while the flowy skirt adds a carefree feel. Pair it with casual sandals, espadrilles, or strappy heels for a night out. 

Striped Poplin Breezy Shorts

Don’t be surprised if you find me at the beach in these poplin shorts. The roomy fit and drawstring waist make them an easy throw-and-go piece, and the breezy cotton fabric will keep you cool on August’s hottest days. Reviewers can’t stop raving about how comfy these shorts are, adding that you can easily dress them up, too.

Eyelet Pull-on Maxi Pocket Skirt

Flowy maxi skirts are the style of the summer. They’re ideal for travel, since they’re breezy, easy to style, and look on-trend in any destination. This on-sale Loft version has a unique, eyelet fabric that adds an ultra-feminine touch, plus a comfy elastic waist. Reviewers praise the airy fabric, which one shopper said kept them “cool and fashionable in the summer heat.” Best of all, this skirt even has pockets to hold small essentials. 

Denim Utility Maxi Skirt

In addition to shopping for summer staples, I’m already keeping an eye out for transitional pieces that I can wear in the chillier months, too. Exhibit A: this stylish, versatile denim skirt. It’s a great alternative to jeans in the summer months, since it offers the same look but with an airier feel. I’d pair it with a white tank and white sneakers for a simple, laid-back ensemble. When fall comes around, I’d add a chunky knit and boots. Snag this three-season skirt for just $23 today.

Gathered Waist V-neck Blouse

If you’re building a capsule travel wardrobe, a romantic blouse should be on your shopping list. This stunning one has a bohemian vibe, flattering hourglass silhouette, and lightweight fabric. It’s slightly cropped, so it will pair best with high-waisted bottoms and skirts. I love that it can be dressed up or down, and it goes with just about anything. Needless to say, it deserves a spot in your suitcase. 

Floral Embroidered Poplin Shirred Mini Dress

If, like me, you aspire to look like you stepped out of Mamma Mia! during your summer vacations, then you’ll love this embroidered mini dress. With blouson sleeves, an A-line cut, and floral embroidery, this dress feels nostalgic without looking dated. Reviewers attest that the linen-blend fabric is lightweight yet opaque, so it’s perfect for hot travel days. I’d pair it with espadrille shoes, although a strappy sandal would look stylish, too.

Welt-trim Linen-blend Mini Skirt

It’s not too late to get in on the butter yellow trend, and this linen mini skirt is one of the most elevated options I’ve seen in the hue. It has a sophisticated silhouette and stretches far past the fingertips, so this skirt is ideal for all occasions. I’d pair it with a crisp button-up for work or dress it down with a white tee for weekend wear. 

Lace-trim Linen-blend Midi Dress

One reviewer called this lace-trim dress “low-key sexy,” and I couldn’t have described it better myself. The lace detailing adds a flirty element without being overly revealing, and the modest midi length balances out the cut-outs. Plus, the breezy fit and linen-blend fabric are perfect for hot summer nights. Based on the reviews, I’d recommend bustier shoppers size up to get the perfect fit. 

Harbor Tank Top

A nautical striped shirt is always a good idea. Shoppers raved about the “heft” of the fabric, which ensures this Harbor top won’t look flimsy or thin. Nonetheless, it’s still the “perfect summer tank,” according to a reviewer. Style it with linen shorts, a pretty maxi dress, or classic jeans for an instantly stylish look. 

Poplin Modern Pocket Shirt

A white button-down may be seasonless, but I reach for mine most often in the summer. With a slightly cropped silhouette and breathable cotton poplin fabric, this standout one is perfect for warm weather. Throw it over a swimsuit, pair it with jean shorts, or opt for an elevated skirt for a dressier look. Snag it for just $39 today, and I promise it will be in your rotation for years to come. 

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