Style 101: The Best Wear-Anywear Outfit Formula

Welcome back to our second post of the new Style 101 series, where I tackle one style related topic and break it down with my personal style tips to inspire you to get the most out of your wardrobe! I received quite a few questions centered around my favorite “all season” staples and what my “go-to” outfits are, so today, I’m excited to introduce you to a foolproof outfit formula that works for me every time!

Secretly, I think I was mentally “saving this post for a rainy day” if you will, when you and I could use a little breath of fresh air and a break from looking at cold winter layers, turtlenecks, and snow boots 😉 Plus, we’ve actually had a few beautiful days here lately where I’ve been pulling out my trusty trench coat (gasp!)–a sign of hope that spring is around the corner!

Neal and I snapped these pictures while wandering around San Francisco this past fall. (Remember this post we shot in Pacific Heights? Swoon!)

I often forget how inspiring even just a quick trip to a new city can be. The chance to explore all the different SF neighborhoods and work from new coffee shops provided a much-needed reset and a general boost of creativity that I often-times feel depleted of when November and December roll around.

Honestly, I hadn’t really looked at these photos in a month or so, I almost forgot they existed! It was so nice looking at those pretty SF streets with fresh eyes all over again! I hope you love them as much as I do! (By the way, I also owe you a San Francisco city guide–so that’ll be coming soon, too!)

Something else I love about today’s outfit–it’s a foolproof framework you can use over and over again in fall, winter, or spring. (Although it would be a litttllee hot for summer 😉)

What I love about this outfit:

Have you ever heard the concept of “KISS?” It stands for “Keep It Simple Stupid” haha–I heard it over and over again during my advertising career but after some digging, I found out that it was actually first used by the U.S. Navy, stating that systems work best if they are kept simple rather than made complicated, therefore, simplicity should be a key goal in design. (More on Wikipedia!) Cool, huh? I think it fits in quite nicely with my “make it simple, yet significant” style motto of 2018 (stolen from Don Draper, obviously. 😉)

Anyway, this outfit just about as classic as they come, and the formula is one that I turn to over and over again in any in-between-season weather–it works when transitioning from fall to winter, to pull out of your back pocket on a warm winter day (when you FINALLY don’t need a puffer!) and then again in the chilly days of early spring. (Or, when you have a trip to San Francisco coming up!)

When it comes to travel, it’s also a framework that I use to get the most out of my travel wardrobe– because I carry-on just about everywhere that I possibly can (including to Europe)–it’s just so much more efficient from both a time AND money perspective, plus, it really eliminates that panic you have when it comes time to pull something out of your suitcase to get dressed, and you realize you really have nothing to wear. By the way, if you’re looking for the perfect carry-on, don’t miss my full review of my favorite suitcase over here!

The Formula:

The Classic Blouse:

Button Down: 

Everlane makes my favorite classic button-down blouses–they have so many and they’re all under $100. I love their new piped versions if you’re going for something a little different. Sezane (a French brand I’m in love with–I need to order some of their basics!) also makes some very beautiful blouses. Everlane also makes a sleeveless silk button down for those of you in warmer climates who don’t need the sleeves! (Jealous!)

Pullover blouse: 

If button-downs aren’t really your thing and you’d prefer a pullover, this one from Everlane is really pretty! Sezane also makes this version that is a pullover in the front but a button-up in the back, with a lower V and beautiful scalloped details on the neckline! Swoon!

For a feminine touch: This version from LOFT has tiny, subtle ruffles at the collar and sleeves for a more romantic look.

Dark, High-Waisted Pants:

Jeans: If you read my post “how to make your legs look longer”–you know why high-waisted dark skinnies are such a secret weapon! They are the most flattering pants out there–the two pairs I own are J.Brand’s “Maria” jeans–I have them in “Bluebird” wash (run small, consider sizing up if you don’t like your jeans super tight) but I also love their black version–(they come in lot’s of variations though, Shopbop has the most selection of J Brand’s that I’ve seen and Amazon Prime shipping!) and for a budget-friendly alternative, Abercrombie’s high-waisted skinny jeans are also amazing and so affordable!

Office pants: If you work in an office environment, you can easily swap out the jeans for a more formal pant, like a ponte pant, or a classic trouser (the Leith trousers are a GG reader favorite, as are Everlane’s pants! LOFT and J.Crew also were voted best place for office pants according to you guys!) based on your office dress code!

A neutral overcoat in a classic silhouette:

My trench coat is one of my favorite things in my wardrobe! I bought it before my trip to London last spring. Because it has a removable liner and hood, it’s actually very warm, so I get a lot more wear out of it than I would with a standard rain coat! I love trenches because they have such a classic look that you can also get away with dressing them up, such as, wearing them out to dinner, for example! You also saw it featured in this post last week!

For colder temperatures, you can also go with a wrap coat (I have this one from Ann Taylor!)

Neutral booties with a low heel:

I’ve worn my Dolce Vita “Cassius” booties (on sale for under $100! They come in black and dark grey, too!) pretty much everywhere this winter. They’re insanely comfortable, even though they have a bit of a heel, I can walk for miles in them. They’re the perfect city girl shoe. The best part about them is that the shaft comes up a bit higher than the average ankle boot, which means your ankles don’t get exposed to the cold! (Their “Stevie” bootie is also similar!) No big surprise here, but Everlane and Sezane also have beautiful pairs that have similar qualities!

Again, if you’re looking to make this look work for the office, it’s really simple to substitute out different shoes. You can always go with a classic neutral pump (or my favorite cap-toe pumps for a Parisian inspired look!)

Neck Scarf:

This is nothing new to a Jess Keys outfit so I’ll make it short and sweet 😂 as always, a neck-scarf is my go-to solution for adding some feminine personality to an otherwise basic outfit. (This is no exception!) Linking some of my favorite scarves below (mine is Hermes–you can get lot’s of second-hand Hermes scarves on The Real Real for amazing prices, FYI!) For tips on how to tie a silk scarf, see my blog post, “How to tie a French style scarf”

Do you have a foolproof outfit framework? I’d love to know what it is!

If you liked this post, make check out more Style 101 posts over in the archives! Plus, I think you’ll love my capsule wardrobe series, where I share my favorite wardrobe staples and how to style them multiple ways to make the most of your closet!

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