Summer starts on sale.
Memorial Day is here, and it’s the smart time to refill your summer wardrobe with some smart finds. The best part? They’re all heavily discounted. It’s like getting end-of-season prices before the season even kicks off.
These picks cover all the essentials you’ll need for the warmer months. Think lightweight shirts for the office, casual knits for the weekend evenings, and shorts for everything in between. Whether you’re gearing up for a vacation or just looking to stay cool and stylish on Zoom, there’s something here for every occasion.
Now’s the time to snag these deals before you need them and prices are back up. From sweater polos to linen pants, you can upgrade your entire summer wardrobe without breaking the bank.
J.Crew
Heritage Cotton Jacquard Polo, $56.50 $98
A blend of vintage charm and modern comfort. Dense, breathable cotton and a windowpane pattern make it perfect for adding a touch of retro style to your summer outfits.
5″ Stretch Chino Short, $29.99 $69.50
With their mid-thigh length, these shorts are old-school cool, making them great for showing off a bit of tan.
Textured Camp Collar Shirt, $44.50 $89.50
This shirt combines a relaxed, boxy fit with a distinctive textured dobby weave, and the vintage-inspired camp collar adds a touch of classic cool.
Vintage Wash Cotton Pocket Shirt, $26.50-$29.50 $39.50-$45
Faded pocket tees are my jam all year round. They’re great on their own or paired with simple chinos for a decade-less look, or layered under an open camp collar shirt.
Performance Spread Collar Stretch Dress Shirt, $49.50 $98
Made of a breathable, all-purpose stretch cotton blend, it works on its own or under a jacket.
Short Sleeve Sweater Polo, $49.50 $69.50
For a knit polo look without the intense vintage vibe. Check out our full guide to the knit polo for more.
7″ Stretch Chino Short, $29.99-$39.50 $69.50
The 7″ chino short is the quintessential summer basic. No need to shop lower-tier stores with deals like this.
Linen Cotton Suit Jacket, $27.99 $178
Classic Straight Fit Jean, $47.59 $148
Charcoal denim has been my preference over dark denim for years now. It easily swaps into the same outfits but can also be styled in ways from rugged to evening appropriate.
Huckberry
Relwen Flyweight Flex Chino, $148 $198
These are the same ones I featured in my outfit breakdown earlier this year. I wear them all the time, and this is the best price I’ve seen.
Flint and Tinder Straight Fit Stretch Japanese Selvedge Denim, $138 $198
Crafted from premium denim sourced from Japan’s renowned Kaihara Mills, these jeans offer a tailored straight fit that’s not too snug. A hint of stretch ensures all-day comfort, making them a versatile choice for all year.
Mystery Ranch 3-Way Shoulder Bag, $137 $229
I’ve had this bag (in a different color) for probably 6 years and I use it all the time. It can be used as a backpack, briefcase, or messenger bag and has a ton of compartments.
Wellen Recycled Cotton Cardigan Sweater, $117 $168
Made from plush recycled cotton yarn, the Wellen Recycled Cotton Cardigan Sweater is a cozy and sustainable choice for cool summer nights. Its rich texture and soft feel will make it your favorite layer. To see how to style it with shorts, check out this link here.
Amazon
Levi’s 501 Original Fit, $50.09 $79.50
I’ve been wearing Levi’s 501 Original Fit since I bought my first new pair in over a decade two years ago. Now, I have a hard time wearing anything slimmer. They were also featured in this week’s article on how to wear light wash jeans here.
Levi’s Classic Western Shirt, $37.87 $69.50
I recently did an article called “My New Favorite Shirt is One I’ve Had for 7 Years,” featuring a similar western shirt from Gap. I also have the darker wash version of this Levi’s one and it’s great.
Timex Weekender, $25.99 $38.44
The Timex Weekender seems like one of the few things that hasn’t gotten more expensive over the last 15 years. Simple style built like a tank that ticks like a bomb.
Dyson Cordless Vacuum Cleaner, $399.99 $599.99
Turbo-charge your dog hair arsenal with the Dyson Cordless Vacuum Cleaner and save $200 this weekend.
Picture Frames, Set of 5, $20.69 $31.99
The worst part about hanging art and photos isn’t the art and photos – it’s how expensive the frames are. Pick up this set of 5 picture frames and make a gallery wall or spread them through your place, all for the cost of lunch.
Traeger Electric Wood Pellet Grill and Smoker, $389 $499.95
The ultimate way to achieve wood-fired taste with 6-in-1 versatility. Upgrade your summer cookouts with precision temperature control and a large cooking capacity.
Bulova Lunar Pilot Chronograph Watch, $373 $625
Only the second watch model to go to the moon and the only moon watch under five grand. For more details, check out our feature here.
Amazon Essentials Quick Dry Swim Trunk, $7.40 $23.70
Amazon Essentials Slim Fit Short, $7.40 $23.70
Bonobos
Primo Chino, $118.30 $169
These are like the gray textured pair I featured recently to great fan-fare but in a lighter year-round weight. I’m a sucker for chinos with a tab button – it instantly brings up the refined-rakishness.
Abercrombie & Fitch
Crotchet Style Knit Polo, $64 $80
This piece offers a super cool vintage feel without making you look like you’re in a costume. It’s 70% cotton and machine washable, making it a practical choice for summer.
Johnny Collar Sweater Polo, $56 $70
With a streamlined, buttonless design and a textured knit appearance for added interest, this relaxed fit top keeps you breezy with shorts. In fact, it pairs great with:
Seersucker Pull-On Short, $48 $60
These 6-inch pull-on shorts in textured seersucker fabric have an elastic drawstring waist, multiple pockets, and a hidden cellphone zip pocket.
Madewell
Low Top Suede Sneakers, $41.99 $98
Suede sneakers for under $50? Heck yeah! These low-tops feature buttery-soft suede and MWL Cloudlift insoles, combining comfort with a sleek look.
Todd Snyder
7″ Pleated Hudson Short, $99 $148
For the man who’s looking for something more from his chino shorts style. These have details like the extended tab button, coin pocket flap, and pleats, which have a new found appreciation in this looser fit era.
Cotton Silk Riviera Polo, $94 $228
Todd Snyder is famous for there knit polos – only issue is they’re normally over $200. Made of a cotton silk blend, finding these for less is rare unless they’re in less core colors.
Champion Midweight Pocket Sweatshirt, $69 $98
Also famous are their raglan sleeve pocket sweatshirts, Ted Lasso basically made a Zuckerberg-level uniform out of them.
Straight Fit 5-Pocket Chino, $74 $148
The off-white / natural jean is one of my absolute favorite swaps in the warmer months. Simply take your favorite outfit, slide these in exchange of your darker jeans and bam! Serious summer style.
Clarks Desert Nomad, $74 $200
Gap
7″ Easy Short, $19 $39.95
A pull-on chino short with an elastic waist. It’s the get-up-and-go short of summer.
Textured Shirt, $27 $54.95
When we lose layers in hot months, texture becomes a sartorial super pwoer. Simple and subtle, this is lightyears from a white short sleeve dress shirt.
Banana Republic
7″ Linen Short, $56 $80
Lightweight texture that looks dressed up.
Linen Cotton Polo, $63 $90
Linen is the tweed of summer. Keep things light and breathable, but it’s not just for shorts and pants:
Linen Cotton Shirt , $35 $50
T-shirts with a linen blend have their own handfeel and weight.
5″ Core Temp Short, $31.50 $60
Just like their Core Temp chino pants but in shorts form, light weight tech designed to keep you cool.
