Try on the Outfit of the Season

Sometimes I write about AI, sometimes I write about big feelings, and sometimes - like today - I enjoy writing essays about style and fashion.

While everyone is talking about last year’s clean girl aesthetic and this year’s the mob wife winter, I do not have the time, money, or patience to follow trend after trend. Instead, I will always vouch for classic pieces and suggest taking a more timeless approach to defining your wardrobe. White button downs, hearty skirts, leather boots, cashmere, denim, etc.

However, I understand the desire (and often yearn) to add a bit of je ne sais quoi, and I’ve finally found the perfect outfit:

Why is it perfect? Well, it’s polished, sassy, and chic, and the overall combination is lethal: one part baddie business woman, one part fashion journalist, and one part amateur dominatrix.

The ingredients are as follows: leather maxi skirt, cozy sweater, knee high heeled leather boot, and a structured bag. I’ve sourced some options for you so send me photos when you start playing around with this dish of an ensemble!

Let’s build the outfit

The leather skirt is the key piece of the outfit, so be picky in terms of cut and fit, and opt for black or chocolate brown. Note the ideal length is mid-lower calf or even ankle.

There are a few great options from the tried and true shopping stops, like Zara, Aritzia, and Anthropologie, linked above. Just promise me that if we’re buying from places that lean more fast-fashion that we’re planning on a) taking good care of these items and b) wearing them lots!

Two other options to consider if you’re on the shorter side are this pencil skirt from J.Crew or this very fun patent doozy of a skirt from Gap. If you’re not ready for a fabric like leather or vegan leather, try a dark grey or black denim as an alternative, like this one from Gap or this stunning one by Good American

For those with a substantial budget who may want to go for investment pieces (and for those that want to peek), you’ll drool over this flared leather midi skirt from Cefinn and this dazzling piece by Malene Birger.

If you have the time, peruse TheRealReal for consigned maxi leather options!

Sweaters are a dime a dozen, so aim for a simple cut like a crew neck or a lightweight turtleneck, and avoid a bulky or overly casual fabric.

1-Tibi (on sale!), 2-Aritzia, 3-Gap, 4-Anthropologie, 5-Old Navy, 6-Gap, 7-J.Crew, 8-Aritzia

The above are a great collection of examples of what would work with your maxi skirt. Check them out and shop from your fav spot. I’m guessing you already may have a few items like this in your closet…

You can step it up with a brushed textured like this, this, or this, or make the outfit less severe with fun sleeve like this. I am also really into this neutral abstract print sweater. Just remember: simple is better! The leather skirt will speak loudly enough for the entire outfit.

The right pair of boots makes this outfit. I’ve struggled to find the right boots but here are a few examples that may be worth your while:

1-Reformation, 2-Zara, 3-Zara, 4-Reformation, 5-Sam Edelman, 6-Zara, 7-Aldo, 8-Everlane, and for you luxe lovers slash day dreamers, 9-Paris Texas, 10-Paris Texas

Everyone seems to be going on and on about the Remy boot from Reformation, but I much prefer the River and Regan boot (4 and 1, respectfully) My personal favs are the ones from Everlane, but I’m interested in the wide-calf option from Sam Edelman as well. The Aldo option looks like it’s got some stretch in the back as well. Delightful! Hot tip: if you get a new pair of boots (or pull out your old ones, for that matter), head to your local cobbler and ask for a sole on the ball of the shoe - it will make them last much, much longer.

For the record, I don’t like curve or kitten heels, round or almond toes, and need shoes to last more than one effing season. As for what will go best with the skirt? Absolutely leather on leather, and keep it simple. No ankle boots or ‘booties’, and for my country-loving girlies (myself included, and looking at you, mom), this is not the time for our beloved cowboy boots.

A simple, structured bag is the final piece. Structured means a pretty firm bag, one that doesn’t lose its shape. I added #6 as a point of contrast and about as slouchy as I’d go for this outfit. Remember: crisp and polished.

1-Louis Vuitton via Turnabout, 2-Poppy Barley, 3-Alaia via Turnabout, 4-J.Crew, 5-Givenchy via VSP, 6-Etsy, 7-Louis Vuitton via VSP, 8-Cuyana, 9-Etsy, 10-Chloe via Mine and Yours

Most of these bags are sourced second-hand. If you’re a first timer to consignment, bags are a *great* place to start. You’ll be pleased with some of the very reasonable prices which are comparable to some basic retailers leather bags.

There you have it, nice and easy. As always, PLEASE REPORT BACK!

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