When it comes to makeup, most of us spend the summer trying to avoid the less-than-chic melting look, and leave it at that. Tragically, this tends to mean an entire season during which red lipstick is considered off-limits, given its reputation as being a labor-intensive look that is, well, prone to getting a bit messy.

It looks like I won’t have to shelve my favorite look until September, thanks to Laura Mercier, who it turns out makes that rare, mythical creation: the perfect red lipstick. Of course, choice of shade varies from person to person and complexion to complexion, but I’m a huge devotee of Truly Red lipstick, which strikes the perfect dark but not too dark balance, which in my experience is no easy trick.

Really though, the entire range of colors is fantastic, and, more importantly, it actually stays put without any smudging or bleeding on even the worst days of a heat wave.

For days when committing to lipstick just isn’t in the cards, though, their lip stains are a great back-up plan — subtle, effective, and easy to apply, both the stains and the lipsticks are a surefire way to beat the heat and look good doing it.

These look like basic rainboots, but these sturdy green staples have been the go-to outdoorsy footwear of the landed gentry for ages, meaning that whenever you see a paparazzi shot of any of the royals on the summer estate, they’re sporting a pair of green Hunters.

Even if you’re not spending your days on the English countryside (it happens to the best of us), these are just as convenient for getting around the city in inclement weather and finally winning the battle against those puddles that seem to extend 3 feet from every curb when it’s been raining.

They also happen to come in a slightly shorter, lace-up style that’s slightly more city-friendly and no less iconic. Classic, comfortable, and built to last, Hunter boots make rainy days not just bearable, but something to look forward to.

These somehow manage to vibe both “secret agent” and “Catskills vacation” at the same time, which is no small accomplishment. For something a little more whimsical (hey, we still have a few weeks of summer left!), I also love this spin on the Wayfarer that looks normal on the exterior but inside features a print of the New York City subway map – you know it’s there, but the rest of the world only occasionally gets a glimpse.

Looking mysterious was never so easy.

The most reliable source I’ve found yet for quality loafers is Etienne Aigner, a great little line that also has a solid collection of gold and silver jewelry, my longtime weakness. While it’s impossible to go wrong with an understated dark brown,  I was beyond excited when I came across this pair in “beach nude,” which is a little more versatile when it comes to summer skirts, dresses, or a good pair of white pants.

But let’s not forget about the jewelry: besides turning out a reliable arsenal of basic hoops, studs, and bracelets, this line features an unexpectedly playful mix of gold and silver on a lot of their pieces. It’s not an easy look to make work, but pieces like this necklace definitely fit the bill, and can add a nice twist to an otherwise subdued work outfit. Gold, meet Silver: it’s time you two got better acquainted.

Staving off frizz and general unruliness is no small task, but in this case a good dry shampoo-flat iron combo will do the trick. Flat-irons can be notoriously damaging if you buy the wrong one, though, so it’s worth investing in a quality ceramic model like this FHI flatiron. I’ve come to swear by – it’ll straighten things out without inflicting any excess damage on your locks.

It works especially well if you prep or even follow up with a good dry shampoo like Frederick Fekkai au naturel to get rid of excess moisture -no one wants to look like they just got back from 6 mile run five minutes after leaving the house. Instead just sprinkle in a little of this — bonus points: it smells great — and you’re good to go. It’s your call whether or not to tell people that you just rolled out of bed with perfect hair.

Thankfully, I came across tortoise Ralph Lauren style a couple of weeks ago, and have been unabashedly obsessed ever since. While both hoops and tortoise are total staples in the world of accessories, you almost never see the two together, which makes for a really fresh and unexpected twist on a classic. The tortoise is also subtle enough that even if you happen to have a day where you’ve really piled on the jewelry (hey, sometimes that’s what it takes to get up in the morning), there’s zero risk of this look going overboard. Instead, it’ll look like you threw on a great pair of earrings from your grandmother’s collection… even if you only bought them last week.

There’s a reason literary types have been carrying these in their bags since the days of Ernest Hemingway (how’s that for cred?): well-made with a classic design, I like to think this is a notebook that says, “I may love my iPhone, but I’m still a person of timeless taste, manners, and style.” At the very least it says “I am a person that remembers to show up,” whether it’s for a job interview or just a friend date. From travel guides to blank sketch notebooks their whole range comes in handy, but I’m a particularly big fan of the week-by-week planner, which leaves just the right amount of space for random notes to self, phone numbers, or a quick sketch of the bizarre person sitting across from you on the train.

This raises a major question of how to replace this go-to summer footwear, and for this, allow me to introduce you to your new best friend, the Sperry Top-Sider boat shoe. A decades-old preppy staple, boat shoes have made a huge comeback over the past several seasons, and with good reason: possibly the most versatile shoe in existence, not only do these look good on ladies and gents of all ages, they’re comfortable for as much strolling (or sauntering) as you’re capable of managing in the heat. A lot of knockoffs have cropped up with their resurgence in popularity, but don’t be fooled, Sperry always has been and always will be the gold standard when it comes to boat shoes.

For such a simple shoe there’s a huge amount in variation between style with these. So far I’ve stuck with a classic dark brown pair, but I’m also feeling this updated color-blocked pair for a little bit of a twist on the look.

And, in case you want to feel like you’re on a yacht, in Miami, or on a yacht in Miami (and really, who doesn’t?), these white ones couldn’t possibly be better:

Like so many others, I’m all too familiar with the classic post-college plight of nailing down a job (or at least a job interview), then having no clue what to wear. As far as I can tell, the trick is to avoid looking like you just rolled in from a night of beer pong, but not overdress like a tuxedo at a beach wedding. Until you’re a CEO, hoodies and power suits are to be avoided. And, of course, all this gets even harder when it’s 85 degrees and humid.

During my crash course in the world of dressing like a grown-up, this BB Dakota blazer has become my saving grace.

Seriously, let me count the ways this blazer is amazing: It’s long enough to work with either jeans or a dress, the grey goes with just about everything, and it’s light so I can still wear it in the summer without worrying about  heat stroke. But besides the fact that it’s unbelievably flattering, my  favorite feature of this is the three-quarter sleeves that scrunch up, a treatment I already inflict on all sweaters and jackets, usually to their detriment. It’s a small detail but makes the blazer great for showcasing bracelets and rings, and also makes it wearable while still a lot more serious than a shapeless cardigan. I’ve done a little more digging and BB Dakota apparently has an entire range of great summer-and-job-appropriate blazers, so I’d call this one item definitely ready to check off the “work clothes” list.

The Victorinox is much more moderately priced – very few exceeding $1000. Victorinox are also steeped in tradition. The company has been supplying the Swiss Army with precision cutlery for well over 100 years. Though they are late to the game, when it comes to watches, my friends who wear Victorinox watches have nothing but good things to say about this hardy ever-growing brand. For my part, I wear a Rolex – my grandfather’s. Vintage. A rose-faced number from the 1950s. Grandpa was a grifter and a small time Detroit hood. Wearing the timepiece about carries with it a certain degree remembrance of him and his more obvious faults. You could say a lot of bad things about gramps but you couldn’t say the man wasn’t a snazzy dresser.