Transitional Wardrobe Staples You'll Rewear from Season to Season

November 19th, 2021 at 3:00pm
Transitional Wardrobe Staples You'll Rewear from Season to Season

As the autumn temperatures dwindle away and the cold weather kicks in, there can be some awkwardness when it comes to creating a killer outfit. While everyone might want to rejuvenate their wardrobe with the latest winter trends, it’s not always realistic to do a major closet overhaul for every changing season. Good thing there’s a simple solution to this fashion nightmare; transition staples. Filling your wardrobe with some classic, mercurial essentials that are perfect for the cooler seasons is the secret to looking put together and stylish for the rest of the year. That’s why I’ve rounded up some standard pieces that will surely guide you from season to season.


PHOTO: @sydneyhopeee

The absolute perfect staple to keep in your closet for each season. If you’re looking for a lightweight piece to add a little dimension to your outfit or looking for a simple layering addition to your ensemble, you have to include this essential in your wardrobe.

Shop Button-Ups

Urban Outfitters Addison Button-Front Blouse

For a trendy, chocolate brown addition to your outfit, layer with this lightweight button up.

Buy now for $59.

Wilfred Free Relaxed Button-Up

Adding a pop of blue with this button up gives you a look that’s equally relaxed and sophisticated.

Buy now for $88.

Madewell Moleskin Sunday Shirt

You can never go wrong with a neutral tan, so check out this classic button up option.

Buy now for $98.


PHOTO: @giselle.rosalie

As you strut your way from season to season, who says you can’t incorporate the same pair of classic booties into your style? Find a neutral pair that will go with the warm hues of fall time and the cool tones of the winter so you’ll be set to go.

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Steve Madden Barclay Booties

If you’re looking for an easy way to spice up an outfit, this sandy leather pair of lug sole booties is perfect for you.

Buy now for $140.

Marc Fisher LTD Alva Bootie

You can never go wrong with a pair of brown block heel booties — they add an effortless touch to all of your fall and winter fits.

Buy now for $120.

Princess Polly Michelle Boot

No shoe collection is complete without a pair of wear-with-everything black booties. This Princess Polly pair is calling your name.

Buy now for $65.

Midi & Maxi Dresses

PHOTO: @genthefashiontrend

I know you’re thinking that maxi or midi dresses are such a staple for nicer temperatures, but why not keep them in your closet all year long? Try adding layers to your favorite, longer dress as the seasons go by and you’ll sport a chic look no matter what.

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Old Navy Sleeveless V-Neck Ribbed Maxi Shift Dress

This simple ribbed maxi shift dress in a warm brown tone will be a versatile layer as the days get colder.

Buy now for $40.

Anthropologie Plaid Midi Dress

This plaid option will carry you through the changing seasons. Just imagine how cute it would look tucked under a sweater or layered over a turtleneck.

Buy now for $198.

Free People Aviva Midi Dress

Even dresses in shades usually associated with spring and summer — like this baby pink — make for great layering pieces as the seasons change.

Buy now for $88.


PHOTO: @amynathalie

Throwing on a blazer will give you that sophisticated, “my life is actually put together” look with any outfit. What’s even better about a standard blazer is that they can hang as a light cover up or as a thick layer.

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Zara Double Button Fitted Blazer

Let’s be real, green should have been the color of 2021! This blazer in a dark olive shade is the perfect fall-to-winter take on a trendy color.

Buy now for $90.

A New Day Plaid Blazer

You don’t need to break the bank to add a staple blazer to your seasonal wardrobe, so head to your local Target for this structured and versatile piece.

Buy now for $35.

Glassons Faux Leather Blazer

Faux leather has been everywhere this fall and it’s not going anywhere come winter. This chocolate brown jacket will remain a closet staple for seasons to come.

Buy now for $80.


PHOTO: @liv_brink

I know that it’s kind of obvious to find your staple pair of jeans that make you feel and look good. However, if you hunt down and claim your favorite pair of denim during one season, you’ll be ready to dress for the rest of the year too.

Shop Denim

Levi’s Ribcage Straight Ankle Women’s Jeans

You can never go wrong with a classic. These Levi’s will travel with you from season to season thanks to their trustworthy and comfortable fit

Buy now for $98.

Abercrombie & Fitch 90s Ultra High Rise Straight Jean

A&F has stepped up their denim game lately, so check out some of their styles for your go-to pair.

Buy now for $89.

Madewell The Dadjean in Eads Wash

Black, gray, and dark wash denim are a must for fall and winter and this Madewell pair is no exception.

Buy now for $118.


PHOTO: @brooklyn.fudge

Loafers —the time-honored pair of shoes that are once again entering the trendy scene — are unquestionably made for the colder months. Whether you style them with a skirt to embrace the autumn season or with some ankle jeans in the winter, loafers are going to be your best friend when it comes to picking an outfit.

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Circus by Sam Edelman Eileen Loafer

If you’re looking to step out and get some attention, these two-tone sherpa and leather shoes are the loafers for you.

Buy now for $90.

Steve Madden Trifecta Platform Loafer

A simple loafer can be paired with any outfit no matter what the temperature is outside — this neural pair adds just enough edge thanks to the chunky platform.

Buy now for $90.

Lattelier Leather Loafers with Chain

Black loafers are flying off the shelves, but hunting down a traditional pair will prove worth the effort since they go with literally everything.

Buy now for $59.

Leather Jackets

PHOTO: @tstacyy

Finding the right leather jacket early on will secure your wardrobe for the end of the year. They just look impeccable with the mild fall aura and the harsh winter ambience, not to mention they can layer beautifully.

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Blank NYC Faux Leather Moto Jacket

This cult-fave Blank NYC moto will be your seasonal essential when it comes to adding a finishing touch to any outfit.

Buy now for $98.

ASOS DESIGN Longline Oversized Faux Leather Biker Jacket

Make a statement by layering with this lilac leather jacket over your favorite sweater and dresses.

Buy now for $57.

Zara Faux Leather Jacket

Another essential option, this black faux leather jacket will be a hero piece in your wardrobe from season to season.

Buy now for $70.

Taking the time to collect your favorite staple pieces won’t just set you up for the transition from season to season, but it will inspire you to experiment with your style. Incorporate some of these classic items as the weather changes so that you can both save some money on shopping (as hard as that is) and save some closet space. Nothing is better than solidifying a few items to rule over your wardrobe and give you some sense of personalization, regardless of the time of year. 

Featured image by @adriannaabreu.