Looking Inside My Closet: How Do I Avoid Becoming a Repeat Offender

It’s the most wonderful time of the year. No, not Christmas fool! The time of the year where wardrobe staples are vital to the lifeblood of your being. Oops, I meant closet. OK, I’ve clearly been watching one too many dramas like Billions, but do you get the point?

Many of us want to wear certain items in our closet without looking like we repeat outfits everyday. Hold up, wait a minute. Scratch that statement because I do not want to speak for anyone.

Let me speak for myself. I want to rock certain items in my closet without becoming a repeat offender. Sure, some people might be OK with wearing the same outfit over and over. Totally fine. However, I try my best to foster creativity when I look inside my closet. Why would I buy a wide array of clothes if I’m never going to wear them? Talk about wasting money..

Thus, with snow/sleet/what-in-the-world-is-that falling from the sky, it is time for hoodies, jeans, boots and coats to rule wardrobes in Wisconsin at least until February. Hopefully not longer, of course.

After a conversation with a fellow reader and friend, Marina, I’ve decided to put together some of the essentials that can be worn three, four, heck five times a month (if not more). Can we all agree it’s difficult to wear a striped sweater 10 times and play it in different ways because of its distinctiveness?

On the flip side, a solid colored hoodie can be played with so many other items – a denim jacket, bomber, overcoat, etc. And what’s best of all? You won’t be caught pulling a double whammy.

Here are some items that can be rocked in many facets during the fall and winter.

God Bless Chelsea Boots
This is probably falling on deaf ears at this point, but Chelsea boots can legit be worn with anything. Joggers? Suit? Ripped jeans? Check, check and checkmate. Shoes are the gateway to flexibility within your wardrobe – once you have a pair of Chelsea boots, your life will never be the same.

New Republic Chelsea Boots
Look familiar? :O My New Republic Houston Sand Chelsea Boots

Opt for suede Chelsea boots similar to mine, or go with leather Chelsea boots if you want footwear that can help you fight through the winter. I’d recommend not wearing faux-suede or suede Chelsea boots once you see snow fall – unless cleaning boots hours upon hours is your thing.

Solid Colored Hoodies
I know retailers like Forever 21 sell extravagant hoodies in wild colors, but a solid colored hoodie from practically anywhere goes a long way. Imagine you have a black hoodie. You could wear it with an overcoat, denim jacket and bomber. That’s three ways right there!

Then imagine you own five solid colored hoodies. That’s 15 potential outfits just because you own simple hoodies that can be played in different ways. Less is more. I own hoodies in some pastel color ways: tan, pink, olive and the ever-so-versatile black. It is harder to “run out of outfits” because I have solid colored hoodies in various colors.

I shop at Forever 21 and ASOS for my hoodies.

Overcoat/Top coat
I just bought this New Look overcoat from ASOS. Thanks to my girlfriend, who is a student, I was able to get it for $76 bucks (check out Unidays if you are a student)! I’ve already worn it with dressy outfits, but also with more laid back outfits.

My coat’s color is camel, but they also offer this coat in black.

Finding a coat that can be worn with different types of outfits, while remaining comfortable, is key. One would argue a coat itself isn’t truly the ensemble for an outfit, but as the temperature drops, I wholeheartedly disagree.

If you have any questions about how an overcoat should fit, check out this article I came across.

How can I talk about fall and winter, and not mention sweaters? Some of you might be scoffing at sweaters and thinking “Old man Justin.” PUMP YOUR BRAKES.

I wore a tan sweater from Forever 21 I bought a few years ago with a pair of blue jeans last week, but it could easily pair well with suit pants or a pair of dark wash blue jeans. Sweaters in cream, navy and black can be thrown together with multiple outfits.

If Granddad/Mr. Rogers/Bill Cosby (leave that man alone) sweaters are not your thing, a less dressy sweater could easily be worn with joggers or chinos if paired with the right footwear.

In the words of my friend Jabari, sweaters are a game changer. Also, please don’t be the guy cracking on the other guy who looks warm in his sweater. Don’t hate the player, hate the game baby!

Do you have these items in your closet already or have you discovered your own staples as fall continues and winter rolls around? Let me know! Peace, love and style!

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