Summer clothing is fun but not always easy and occasionally confusing.
How can I look stylish while staying cool? Do I have to wear a suit jacket when it’s 95 degrees outside?
At least during autumn, you can throw on a peacoat over any old outfit and look Cary-Grant-adjacent.
As a born-and-bred Angeleno, I spent a lifetime developing instincts and best practices for summer dress. Then 15 years ago, I moved to, and stayed in, cities with real seasons, one of which has an actual Fashion Week (first Boston, then New York).
By comparing different seasonal wardrobes, I grasped the whys and hows of each from a practical and aesthetic perspective.
So, here’s my foolproof system for summer style. Look good. Stay cool. You’re welcome.
Shoes
Breathable shoes are of the utmost importance.
Fortunately, the hybrid shoe market has come a long way since the days when heritage brands thoughtlessly stuck athletic soles on leather derby uppers and called it a day. Avoid those brands and look for modern shoemakers like Wolf & Shepherd that combine running shoe tech with Italian leather.
Their SwiftKnit Loafer is oozing with cool factor and comfort. The navy version is particularly summery.
I like the versatility these loafers provide for summer outfits. Whether it’s dinner and drinks or a food truck festival, I can pair these with chinos, shorts, or slacks and be dressed to impress in comfort. You also get a thermal rubber outsole for traction and the protection of a TPU sole, both unusual features for loafers.
Take any outfit you’d typically wear with boat shoes, and go for either of these shoes instead. It’ll look more modern and distinct, but not faddish.
Summer Tailoring
Since we often associate suits with structured, wool constructions, they might be more confusing to navigate in the summer.
Even if you’re not in formal tailoring often, remember that weddings are commonplace in June. Plus, suit separates are a great way to level up casual outfits.
Suits and Suit Separates
You absolutely need a summer suit. This is a menswear essential. They’re light, breathable, and versatile since they aren’t always as structured as a traditional suit.
I recommend getting one in a light color and one in a slightly darker color—though you never want to go full black or dark navy in the summer. A medium slate or marine blue works.
A cream linen suit often features subtle texturing, which is the nature of the fabric, giving it a resort chic vibe. Think off-duty Bond.
I always say a guy who’s mastered resort wear is a man who’s mastered casualwear in general.
Bamboo or silk-blend suits have a subtle sheen to them, which makes them perfect for formal occasions.
My recommendation? Get a linen suit in a lighter color and a silk or bamboo blend in a darker one.
Some recommend lightweight wool, but honestly, linen will go a longer way. Lightweight wool suits are great when it’s 70 or even 80 degrees out. Linen or silk blends will take you from a 70-degree day at the beach club to a 95-degree outdoor business lunch.
Two other pieces of tailoring that I fully advocate for are slacks and dress shorts. It’s all about picking pieces that can be worn in several different ways.
Slacks are like lighter, looser dress pants, but they aren’t made in a set. This means they don’t have a matching jacket. Technically, they’re a smart casual piece, but they can be worn with a contrast-color suit jacket.
Dress shorts are basically just highly hemmed dress pants. Wearing them with an actual suit isn’t for everyone (nor is it appropriate in many dress codes). However, they pair well with a linen dress shirt, polo, or even a t-shirt.
Seersucker suits are another summer option with a nautical and preppy vibe. There’s a time and a place for a whole seersucker suit. Perhaps a fundraiser luncheon at a boat club. This isn’t relevant to everyone.
However, if it’s your thing, a pair of seersucker shorts or even pants pair well with boat shoes and a casual top on a summer day.
Dress Shirts
Again, linen is a saving grace here. Not only are linen shirts light and breathable, but they tend to be less architectural and stuffy. Linen dress shirts in shades of white pair beautifully with a full suit or even shorts and drivers.
Poplin is another material to consider for your dress shirts. It’s strong, light, and breezy, and it drapes softly. Even more, poplin wicks moisture and odor. I actually prefer poplin to cotton all year long because its tighter weave often results in a richer color.
Short-sleeve dress shirts have a reputation for being anti-fashion. However, if you get them tailored, they’re a flattering and practical addition to a formal summer wardrobe. The sleeves should land mid-bicep.
If you haven’t had an opportunity to tailor your shirt, go for a vintage look by rolling them up, James Dean style. Fold the sleeve in at your inner arm so that it hugs your bicep, then start folding it up until it’s stable.
Remember how I said dressy clothes are a good way to level up casual outfits? At the beach, you can wear a short-sleeve dress shirt, open, with a tank top underneath.
Or you can just wear a dress shirt, buttoned up, with some chino shorts and sneakers basically in any non-formal, non-professional context.
Non-Dress Shirts You Can Wear With a Suit or Suit Separates
In the summer you can wear any shirt with a suit as long as it has a similar silhouette to a dress shirt.
Camp collar shirts, knit polos, and even guayabera shirts are all great choices.
Of course, you can even team up your suit and suit separates with t-shirts for a smart casual look. I’ll get to that momentarily.
Smart Casual Style
When in doubt, go for a smart casual approach.
Summer is generally a more relaxed season. However, by adding just a little bit of structure to an otherwise simple combination, it can look effortlessly sophisticated.
For example, go for a polo or henley shirt with your shorts instead of just a crew neck. Or, pair your crewneck with drawstring chino shorts instead of atheltic shorts.
And remember, summer versions of formalwear are lighter, and therefore, much easier to combine with casual pieces. So feel free to mix and match from the tailoring up top with the recommendations below.
Smart Casual Tops
A t-shirt can be casual or smart casual, depending on how you style it. These days, there’s nothing wrong with wearing a crewneck with a suit, especially in warm weather. Find a tightly-woven, well-structured shirt.
You can even wear it with slacks and loafers for a simple look that’ll make your accessories pop. Perhaps you’re wearing a nice watch, sunglasses, or hat.
Linen button-downs are just as snazzy, but not as stuffy, as linen button-ups.
And as with most of your summer wardrobe, stick to shirts in lighter colors. Think light blue, creams, mint, faded yellows, and muted grays.
Smart Casual Pants and Shorts
Chinos are a smart casual staple, and you can make them more summery simply by cuffing them. Besides, nothing’s more seasonally attractive than showing a little ankle.
Go for pants in the lightest grays or tans, steel blue, or even light yellows. Not sure you can pull off yellow chinos? Wear them with a heathered gray top to temper the brightness. A sun-faded rust hue can take you from summer to fall.
Slacks are just as useful in smart casual combos as they are with tailoring.
Many modern brands make “dress pants” with extra stretch, making them look and feel like slightly slimmer slacks.
Then there are brands like Mugsy, which makes a stretch chino. It’s less rugged than typical chinos but more casual than slacks. Think of summer dress pants and chinos as a spectrum between comfort and formality.
The smart casual realm is a good place to experiment with short colors. While spring is all about the light hues, summer is all about the bright hues. Shorts don’t take up a lot of real estate on your body. So, shorts can often serve as more of an accent.
For example, bright salmon shorts with a cream linen shirt and boat shoes are a perfectly seasonal combination. It looks great at the beach or while running errands.
Smart Casual Shoes
For the warm seasons, you want something athletic but sleek, and something dressy yet practical. For the former, I often recommend low-profile white sneakers. For the latter, a nice suede driving moc.
Or, you can just go with one pair of SwiftKnit Derbies from Wolf & Shepherd. Since I already spotlit SwiftKnit Loafers, I’m going to give these guys some love too.
The SwiftKnit Derby features Wolf & Shepherd’s proprietary FloatFoam memory foam footbed, which offers extra padding in the heel and contours nicely around the sides of my foot. They're futuristic looking and super comfortable.
It’s a truly unique design that combines Derby shoe architecture with athletic shoe materials, checking both boxes.
An Overview of Summer Casualwear
At your most casual, you can wear a t-shirt and shorts. Why not? Just choose well-fitted pieces.
My only suggestion here is that, if you’re not beholden to a dress code, really lean into the summer palette. Pick a light blue shirt, and bright red or even orange shorts. Then finish it off with some white sneakers.
Try Madras shorts for that Nantucket aesthetic. Jeans might be too heavy for summer, but chambray isn’t.
For shoes, you’ll want a nice sandal and some comfortable, athletic trainers.
I recommend full-grain leather sandals or nice canvas espadrilles. You don’t need both since they’re each made to be breathable and sand-friendly. It’s just a matter of personal preference.
When it comes to trainers, the All-Birds aesthetic is both fashionably relevant and practical because of its soft and breathable construction. I’m going to highlight Wolf & Shepherd one more time because their SupremeKnit Trainer comes in a wide range of expressive yet still neutral colorways.
I can't recommend this model enough if you're looking for something on the sportier side. The lightweight, breathable cotton knit and stylish Italian leather detailing embody the smart casual mantra, not to mention how comfortable the materials are.
Oh, and you can always level up a simple t-shirt and shorts with some cool accessories.
Summer Accessories
Here’s a list of accessories you might consider for the summer:
- Sunglasses – Wayfarers are summer classics, but if you want a more Top Gun aesthetic, you can’t go wrong with aviators.
- A sport watch – Divers are a great choice in the summer. You can put them on a rubber or Nato strap for a rugged, nautical look on more casual days.
- A classic straw hat – A trilby or Panama hat has a cosmopolitan vibe to it.
- Belts – You can stick to leather if you want, or go for a nautical canvas with leather accents. Otherwise, going for a braided leather belt over a simple one adds a touch of fun. And isn’t fun what summer is all about?
Conclusion
The key to getting an elevated summer look is mixing and matching the three dress codes: Trainers and shorts from the casual realm, then a linen dress shirt from the tailoring section.
And again, I highly recommend playing around with summer colors—even if it’s just an orange watch strap.
If there’s ever a time to take yourself a little less seriously, it’s summer.
