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Style Guide: Outerwear

Outerwear is not only functional and essential in the fall/winter seasons but a key way to maximize your wardrobe year round through layering! Layering meaning literally adding layers of clothing to your base outfits like jeans + top or a dress.

Here are some key styling tips to keep in mind for the outerwear category:

  • Nail your base outfit and let the outerwear compliment

  • Investing in base pieces is KEY to have elements that fit well with your outerwear (i.e. bodysuits, tanks, t-shirts, mock necks, etc.)

  • If you are going to go with flowy, roomy, oversized outerwear, consider pairing with more fitted pieces with some tailoring and structure underneath for a balanced look

  • If you do have more fitted outerwear (i.e. fitted leather jacket) you'll want to pair this with fitted tops/dresses so it fits comfortably. Balance your look with a fitted midi/maxi dress or bottom fitted/slightly less fitted (i.e. straight leg jeans, wide leg trousers, maxi skirt)

  • Outerwear with belts will add shape

  • Consider a mix of lengths so you have some shorter options that hit at or around the waist and below the waist to create balanced looks

  • Consider casual options and options that are more elevated and you can dress up / down (like the wool coat!)

Now, let's talk about some basic categories of outerwear (yes there are a TON of options in this category!!) and then go into each:

  1. Blazer

  2. Vests

  3. Cardigan

  4. Casual coat

  5. Pullover/Sweatshirt

  6. Denim jacket

  7. Leather jacket

  8. Trench coat

  9. Wool coat

  10. Winter coat

  11. Fur coat


The options in this category range from casual puffer options to more classic quilted vests. You've also got some cozy knit styles that can give a more elevated feel. Pair a vest with your go-to athleisure or denim + top outfits for a cool look.

A classic quilted with gold hardware gives off a more preppy feel but can still be dressed down

A more casual quilted can be paired with athleisure or a jeans/top look

You've also got the sherpa style / fuzzy options, puffer vests (more oversized feel), and faux leather

Faux leather option to dress up or down (very warm) go for all black look or pair with white/cream/color for contrast

This one is on the pricier side but basically a 2 for 1! Also on sale...

And this one...same boat reversible!


You've got your classic (and more preppy style) cable knit cardigan with buttons for which some even come in matching sets these days to get the matching sweater style top to wear underneath. The more casual shawl style without buttons can have a more casual feel, like the popular Barefoot Dreams options. Cardigans vary in length as well.

Pair a flowy cardigan that hits below the waist with fitted bottoms and tank/bodysuit

Opt for a sweater top and cardigan set for an easy look and 2 for 1 (which you can't beat). Pair with denim, trousers, or a skirt

A duster or "sweater blazer" that is longer and to knees / mid calf will have a slimming effect. Check out the "duster" style for options in this category that you can dress up or down.

Love the pairing of a camel/beige/cream with a camisole and monochromatic look

Denim jacket

The classic blue is a go-to but there is also white, light blue, black to think about incorporating to maximize your denim jacket options. Further you've got the fitted style and oversized to play with - the fitted is more versatile to dress up and down whereas the oversized is more casual. A denim jacket is a great option to make any look, even a nicer floral dress, more casual and allow you to give that same piece a whole different look.

Classic Madewell blue/black/white can be paired with dresses, leggings/top, shorts/top outfits easily for warmth and to mix up

Classic Levi's option for denim on denim look

Leather jacket

The go-to to add just a little bit of edge to any look. Wear it on or over the shoulders for a chic look. Go for a fitted or a more roomy/oversized style. Further play with black (classic), white/cream, or a color! You've got options for this staple piece.

Leather jacket with jeans and a tee

Leather jacket paired with a with a flowy dress

White as a cool, different leather option you can wear year round (and fun option for our bride babes!)

Leather with fur for an elevated play on this leather option

Suede as an option too in this category


Elevated casual in a blazer and a tank (like a camisole) and denim. Go most casual pairing with sneakers, dress up in pumps, nice sandals, boots.

Dressing business professional in a blazer + slacks combo. Note that it doesn't need to be matching to be professional but a matching set is the most professional option.

Fitted blazer paired with a tee/tank, jeans, and a belt

Casual coat

Just as it sounds, this is your most casual coat options to throw on over athleisure, pair with jeans/legging + sneaker looks and stay warm in the cooler seasons. Also adding in the ever popular SHACKET into this category!

Pair a cream option with an all black outfit

Go for the currently very popular and trendy chocolate brown with black or an all neutral look

A cozy option with a hood is always a good idea (then you might not need a hat!)

The shacket doesn't need to be plaid, though there are many plaid options available. You can go for a leather/ faux leather or shearling option


Who doesn't love this category and finding a piece in this category that is your go-to year round...or maybe even a super fashionable option...

A pullover in this trendy style below or cozy H&M option to throw on over leggings

Or a pullover like the ever popular scuba

Casual quilted puffer over athleisure (Free People look a like - their go-to, super popular packable puffer here

Sweatshirts over turtlenecks and paired with bikers/leggings like we've all seen with the popular Anine Bing option / something similar varsity style.

Wool coat

Such a chic, classic option and essential to have in your wardrobe and ideally in a neutral color like beige/camel, white/off-white, grey, or black.

Pair a longer option that is below the knee with any length dress - midi, maxi, mini

The pea coat style that is above the knee is great for top/bottom outfits and mini dresses

Paired with skirt + sweater + boot combo

Robe style over a dress

Trench Coats

Classic, versatile, warm but not too warm making it appropriate for year round wear. Go for one with buttons as the most classic style or one without that gives more of a casual look!

Furs or faux furs

The perfect option to wear over any of your more elevated holiday looks and make a statement, throw on for date night, wear for your winter vacays, and more. The faux options have gotten crazy good where you can barely even tell they are faux these days...

And last, your heavy winter coats

Whether you need the full blown "sleeping bag" to brave the winters or just an option for winter vacays and throwing on 1 month out of the year, this is the functional category of coat where you want good quality and not to mess around, while of course still thinking about a style and something you'd like to wear.

Which category is your favorite?!

Want help selecting the right leather pieces for YOU, per your body type, complexion, budget, and more? Book one of our virtual styling services and 1:1 time with a Pro that can curate looks & advice just for you in our app!

Just have styling questions? You can also chat with the Prept Team in our app / text us anytime @ 855-582-3573

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