The summer sale begins.
With Memorial Day fast approaching, it’s the perfect time to stock up on your summer wardrobe with some clever bargains, and the best part is, they’re all deeply discounted — like end-of-season prices you can buy before the season even begins.
These picks cover all the warm-weather essentials you’ll need. Think lightweight shirts for the office, casual knits for weekend nights, and shorts for everything in between. Whether you’re gearing up for the holidays or looking to stay cool and stylish on Zoom, there’s something here for every occasion.
Now’s your chance to grab these great deals before you need them and prices soar again. From sweater polos to linen trousers, you can upgrade your entire summer wardrobe without hurting your wallet.
J.Crew
Heritage Cotton Jacquard Polo$56.50 $98
Vintage charm meets modern comfort with its dense, breathable cotton and windowpane pattern, perfect for adding a touch of retro style to your summer outfits.
5 inch stretch chino shorts$29.99 $69.50
These mid-thigh length shorts have an old-school cool vibe and are perfect for showing off some tan.
Textured Camp Collar Shirt$44.50 $89.50
This shirt combines a relaxed, boxy fit with a textured dobby weave, and the vintage-inspired camp collar adds classic cool.
Vintage Wash Cotton Pocket Shirt$26.50 – $29.50 $39.50 – $45
Faded pocket tees are a favorite of mine all year round. They look great on their own, but can also be paired with simple chinos for a decade-dated look, or layered under an open-collar camp shirt.
Performance spread collar stretch dress shirt$49.50 $98
Made from a versatile, breathable stretch cotton blend, it works great on its own or under a jacket.
Short Sleeve Sweater Polo$49.50 $69.50
For a knitted polo look that doesn’t feel vintage, check out our complete guide to knitted polos for more details.
7 inch stretch chino shorts$29.99 – $39.50 $69.50
Seven-inch chino shorts are a summer staple, and with deals like these, there’s no need to shop at lower-tier stores.
Linen cotton suit jacket$27.99 $178
Classic straight fit jeans$47.59 $148
Charcoal denim has been my favorite over dark denim for years now because not only can it be easily incorporated into the same outfit, but it can also be styled in a variety of ways, from casual to evening.
Hackberry
Relwen Flyweight Flex Chino$148 $198
These are the same ones I featured in my outfit breakdown earlier this year, which I wear all the time, and these are the cheapest prices I’ve seen.
Flint & Tinder Straight Fit Stretch Japanese Selvedge Denim$138 $198
Made from premium denim sourced from Japan’s renowned Kaihara mill, these jeans offer a tailored straight fit that’s not too snug, with a slight stretch to ensure all-day comfort, making them a versatile choice all year round.
Mystery Ranch 3-way shoulder bag$137 $229
I’ve had and use this bag (different colors) for probably 6 years now. everytimeIt can be used as a backpack, briefcase or messenger bag and has multiple compartments.
Wellen Recycled Cotton Cardigan Sweater$117 $168
Made from luxurious recycled cotton yarns, the Wellen Recycled Cotton Cardigan Sweater is a cozy and sustainable piece for cool summer nights. Its rich texture and soft feel will make it your favorite layer. Check out this link to see how to style it with shorts.
Amazon
Levi’s 501 Original Fit$50.09 $79.50
Two years ago I bought my first new pair of Levi’s 501 Original Fit in over a decade and I’ve been wearing them ever since. It’s now hard to fit into a tighter pair of jeans than these, which I also covered in this week’s post on how to wear light wash jeans.
Levi’s Classic Western Shirt$37.87 $69.50
I recently wrote an article called “My New Favorite Shirt is the One I’ve Had for Seven Years,” in which I featured a similar western shirt from Gap. I also have a dark wash version of this shirt from Levi’s and love it.
Timex Weekender$25.99 $38.44
The Timex Weekender appears to be one of the few that hasn’t increased in price in the last 15 years. It’s simply styled, built tough like a tank, and ticks like a bomb.
Dyson cordless vacuum cleaner, $399.99 $599.99
Step up your dog hair game this weekend with a Dyson cordless vacuum and save $200.
Photo frames, set of 5$20.69 $31.99
The biggest challenge when hanging art or photography is not the art or photos themselves, but the price of the frames. Buy this set of 5 frames to create a gallery wall or display throughout your home, all for the price of lunch.
Traeger Electric Wood Pellet Grill & Smoker$389 $499.95
The ultimate way to achieve wood-grilled flavor with 6-in-1 versatility. Elevate your summer barbecues with precise temperature control and large cooking capacity.
Bulova Luna Pilot Chronograph Watch$373 $625
It was the second watch model to go to the moon. only Moonwatches under $5000. Check out our feature here for more details.
Amazon Essentials Quick Dry Swim Trunks$7.40 $23.70
Amazon Essentials Slim Fit Shorts$7.40 $23.70
Bonobo
Primochino$118.30 $169
These are similar to the grey textured pants I’ve been loving lately, but they’re lighter and can be worn year-round. I love tab button chinos – they instantly give off a sophisticated and dapper vibe.
Abercrombie & Fitch
Crochet style knit polo$64 $80
It’s got a really cool vintage feel without looking like you’re wearing a costume, and it’s 70% cotton and machine washable, making it a practical piece to wear in the summer.
Johnny Color Sweater Polo$56 $70
With a sleek, buttonless design and textured knit look, this relaxed-fit top is cool enough to pair with shorts. In fact, it pairs perfectly with:
Seersucker pull-on shorts$48 $60
Made from textured seersucker fabric, the 6-inch pull-on shorts feature an elasticated drawstring waist, multiple pockets and a hidden zippered cell phone pocket.
Madewell
Low-top suede sneakers$41.99 $98
Suede sneakers for under $50? Awesome! These low-top sneakers are made with buttery soft suede and MWL Cloudlift insoles for comfort and a sleek look.
Todd Snyder
7 inch pleated Hudson short$99 $148
For men looking for something more Inspired by chino short style, these pants feature details like extended tab buttons, coin pocket flaps and pleats, giving them a newfound appreciation in an era when a relaxed fit is desired.
Cotton Silk Riviera Polo$94 $228
Todd Snyder is known for their knitted polos, but the only problem is that they usually cost over $200. They’re made from a cotton-silk blend, and it’s rare to find them for less than this unless they’re in a very core color.
Champion Midweight Pocket Sweatshirt$69 $98
The raglan sleeve, pocketed sweatshirt is also so well-known that Ted Lasso basically created a Zuckerberg-level uniform out of it.
Straight Fit 5 Pocket Chino$74 $148
Off-white/natural jeans are one of my favorite pieces for the warmer months, just take your favorite outfit and swap it for a darker pair for some serious summer style.
Clarks Desert Nomad$74 $200
gap
7 inch easy short$19 $39.95
These pull-on chino shorts have an elastic waist, making them perfect for summer.
Textured Shirt$27 $54.95
When you want to avoid layering in hot weather, the texture of the fabric is a big part of the appeal of fashion. This simple and understated shirt is a stark difference from a white short-sleeved dress shirt.
Banana Republic
7 inch linen shorts$56 $80
A light texture that gives a dressy look.
Linen cotton polo$63 $90
Linen is the tweed of summer. Use a lightweight, breathable material and it’s not just for shorts or pants.
Linen cotton shirt $35 $50
Linen blend T-shirts have a unique feel and weight.
5 inch Core Temp Short$31.50 $60
Like our Core Temp Chinos, these shorts are designed to keep you cool with lightweight technology.
