How to Winterize Your Wardrobe for Cheap

Hi everyone! I’ve got a great guest post from Michelle over at See Debt Run today. Michelle is a mom to three adorable monsters, a future volleyball superstar (hey…don’t stop believin’), a lover of sushi, a box wine connoisseur, and a blogger over at See Debt Run, the site that puts the “personal” in personal finance. Today she is going to write about how to winterize your wardrobe so you can stay warm and save money in your pocket.

Why does it always feel like the end of winter goes by a lot slower than the end of summer? I blinked and it was August. To some, that means school is about to start back. For others, that means that they’ll once again have to learn to love their dull winter skin. For those who love to bargain hunt, it means end of summer clearance events!

Most people view these sales as the stores’ way of getting rid of all the junk that no one else wanted. As someone who has worked in retail before, I know that there is some truth to that, but if you’re sale-savvy, you can nab some great deals on some really cute clothes. This can improve your cost-per-wear significantly.

Also, I want to wear my sale items immediately and not have to put them away for several months! Therefore, I’m asking myself several questions while working a sales rack. Will I be able to wear this more than a few months out of the year? If it’s a top, is it easily layered? Is there anything about it that screams “summer only?” If it’s shorts, could I layer them with tights underneath? If the answers are “no,” “no,” and “For the love of God, no!” that doesn’t necessarily mean that the item isn’t an amazing find! It just means you probably won’t be able to wear it year-round.

Obviously, not all of my clothes are multi-seasonal, but a lot of them are. It’s much more cost-effective to shop that way. Since we are currently in debt, I wasn’t able to shop many sales these years, but I did spend some of my birthday money on a few versatile items that can be layered and winterized, so to speak, but were also ready to wear now even in the balmy triple digits we’ve been baking in lately here in the Midwest.

Tops, Tanks, and Shells

These are the easiest to winterize! As long as you don’t buy lime green, this is a breeze. (Note: If you are blessed with a skin color that doesn’t look awful in lime green come November, go on with your bad self, you rule-breaking trailblazer! I for one look like Snow White after a few weeks away from the pool, and Snow White doesn’t look good in lime green.)

Winterizing tops is easy as most can be paired with a cardigan, layered under a low sweater, or worn with a jacket. Piece of cake! It’s so easy, I don’t even have anything else to write, so I’m going to sit here patiently while you wipe tears of joy from your face!


While going through my closet a few weeks ago, I discovered two pairs of shorts that can be layered with tights but can also be worn right this minute with a light peasant top or even a simple tank. The first pair is one I’ve had for years—plaid mostly with browns and taupes, and very neutral. They’re cute today with a nearly sheer white top and brown leather heeled sandals but will be cozy and chic this winter with brown tights, riding boots, and a chunky boyfriend-style sweater and contrasting scarf.

The second pair is basic black poly-blend with belt loops. Right now, these look hot with a silky halter and sling back heels for a date night. This winter, I can add opaque tights and a jacket or cardigan and wear out for drinks with my friends. Obviously, this can’t be done with all shorts. If they’re hot pink, orange, green, or yellow, you probably won’t be able to try this, but grab a pair of your darker or neutral-hued shorts and start adding layers! Being fashionable definitely involves taking risks and trying new things!

Summer Dresses

When I think of a summer dress, I think light and airy, one made of chiffon and unicorn toots. I happen to have several as they’re super versatile and easy-as-pie to throw on in the morning, even when I’m running late. Who am I kidding? I have 3 kids. I’m always running late and having the ability to be almost completely dressed in one step this summer has been a total lifesaver.

It breaks my heart to think about having to say goodbye to my breezy dresses this fall and winter, so I’m just not going to! At the end of the season, I like to go through my dresses and find creative ways to wear them year-round.


Again, this is going to involve some time and creativity. A lot of jewelry and accessories are already versatile enough to spice up your outfit throughout the year, but some will need tweaking. For belts, I’ve actually snatched the belt off one of my dresses that was way summery and wore it several times that winter. The dress was too bright, but the belt was perfect for pairing with my winter loot. I also have a few necklaces and bracelets that are adorable now but would never look right in the winter without some tweaks.

One of my necklaces has stones made out of smooth white shells in the shape of flowers, separated by loops and pearls. The loops and pearls say it could be cool weather jewelry, but to really push it through the seasons, I plan on stringing a simple black ribbon through the loops and tying a pretty bow at the end. It will take me two minutes and I will have a one-of-a-kind necklace that easily transitions from July to January.

Time And Creativity…And Time

Being fashionable yet frugal can definitely be time-consuming. We all know it’s a whole lot easier to just buy all new clothes at the beginning of each season to ensure you’ll be stylin’ and profilin’ for the next few months. It’s easier yes, but is it better? I personally don’t think so. I think even after we’ve climbed out of debt and have found ourselves in a more comfortable financial place, I won’t stop being creative with my wardrobe. I like when I can put an outfit together and confidently walk down the street knowing that no one else is going to be wearing the same exact same thing!

Think about setting aside some time at the end of each season to assess what you have. Set aside a few hours to just go through your clothes and try everything on. If you are like me and wanting to save money, go shopping in your closet and keep an open mind. I know a lot of people who have a set of winter clothes and a completely different set of summer clothes. They simply switch them all out at the end of the season, but that honestly makes me sad!

Think of all the items *you* have right now that could be worn today and layered in the winter. You probably have a lot more than you think and might not even need to take advantage of any of the sales I talked about! Before you toss aside an item that you’ve deemed wrong for the coming season, ask yourself why. Then ask yourself what it would take to make it right. You might be surprised just how many cute outfits you actually have.

2 thoughts on “How to Winterize Your Wardrobe for Cheap

  1. I really like reading through a post that can make men and women think. Also, thank you for allowing me to comment!

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