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How to Wear It

How to Wear It

Happy First Day of Fall!

Let’s kick off the new season with How to Wear it.

Here I take some of your favorite items and help you create outfits and expand your wardrobe by showing you how to get the most out of your closet.

When I was a stylist, one of my favorite things was to help clients create outfits, combining pieces they already had with new purchases. This is the essence of wardrobe building: finding new combinations, keeping it fresh, and adding additional pieces when needed.

Today, I’m using this best-selling J. Crew Factory mock neck sweater as our key piece. This outfit may look simple, but there are a few important reasons why I used certain items.

How to Wear it

Mockneck sweatshirt in adobe, power straight dark jeans, tan lug booties, gold rope hoop earrings, and nude lipstick

Mockneck Sweatshirt, $35 | Power Slim Straight Jeans, $35 Rope Hinged Hoop Earrings, $95 | Lug Bootie, $265 | Lipstick, $38 

We featured this sweatshirt on Monday in our J.Crew Factory round-up. It’s only $35 and feels like fall. Yes, it’s a sweatshirt, but it’s a polished one, so you get a composed look when you pair it with other polished pieces. 

It comes in various colors, but adobe was the most popular and is available in sizes XXS – 3X

Next, jeans. Don’t overcomplicate things here; keep it simple with a pair of dark wash jeans. Above are the Power Slim Straight Jeans from Old Navy, another bestseller. They are an updated take on the skinny as they are not skin tight but still give you a slim leg.

You can pick these up in any size, including petite and plus. Always size down; these stretch out quickly. 

Then, I used the popular, splurge-worthy Tory Burch Lug Bootie. These are still on sale for 30% off, helping you save over $100, your choice of black or tan. 

Because the sweatshirt is thick, you want to balance its weight with your shoe; that’s why I’m using the Lug Bootie. Of course, you could also use the heeled leather boots from the J.Crew factory (another bestseller) or any tan bootie you already own. 

A pair of on-trend gold hoops are a lovely touch. You can use anything, so look through what you have before you buy something new. I love these pretty Rope Hinged Hoop Earrings from Bloomingdales for $95. 

Finally, if you wear lipstick, be sure it compliments the color of the sweatshirt. You don’t want anything too pink. This YSL lipstick is one of my go-to’s in light beige nude. It’s the perfect, subtle hint of color. 

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Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and this post is not sponsored or paid for by the brands or retailers featured.

Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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How to Wear It

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Wanda fouts

Friday 24th of September 2021

Would love to receive my wardrobe checklist

Dian Eckstrom

Friday 24th of September 2021


I love my daily emails from TWDL. I have been working on reducing my closet for the past few months. I am just about ready to start replacing my wardrobe with better, smarter pieces. I have been a member now for several months, and have not received my Wardrobe Checklist. This would be very helpful to have before I begin investing in new pieces.

Thank you!! One Zoomed-out Teacher!!


Wednesday 22nd of September 2021

I have a question about this post, because I'm a little confused. First, the outfit is totally cute, and I can see how all of these items go together well. You even start by saying that there are important reasons why you chose the specific pieces that you did, and this is the information that I'm looking for - trying to learn WHY certain things make an outfit look great vs just okay. Specifically, when you discuss the shoes, you comment that because the sweatshirt is thick, you want to balance it with your shoe, and that is why you selected the Lug Bootie. So far, I am following what you are saying, and understanding why I would want to put a more rugged looking shoe/boot with this outfit. But then you offer an alternative selection for the boot -- the J Crew bootie is much finer/less rugged than the Lug Bootie (I would categorize the JCrew bootie as something I might wear with my work clothes or dressy casuals, whereas the Lug Bootie is definitely something I would wear with casual clothes.) But you don't say anything about why you chose that alternative, which doesn't - at least to my novice eye - seem to match the description you just gave for what kind of footwear goes best with this outfit. So now I am confused! If the Lug Bootie, with its thick sole and rugged look, is what is needed to balance out this thicker, sweatshirt-style top, then why is the more fine cut bootie going to work with it, too? What if I had the choice between a shoe that was similar in style to the Lug, but in a different color (perhaps black) or one that was the burnt orange color and similar in style to the JCrew bootie - which one would be the better choice? I'm asking this because I'm trying to learn how to put together my own outfits, and not necessarily replicate the ones that I see posted. Thanks!

Megan Kristel

Wednesday 22nd of September 2021

The J.Crew bootie can easily replace the Lug boot because it still has weight, even though it's sleeker. In this case, you wouldn't want to wear something like a ballet flat.

Deborah Arcaro

Wednesday 22nd of September 2021

Hi Megan, I enjoyed this post as I do all of your posts. I have been a fan of Old Navy’s Power Slim Straight Jeans look. However, I’d like to know how tightly they should fit. I’m an athletic build and don’t “fill out” the hips in any jeans. I’m so used to the look of my skinny jeans that I’m not sure how loose the straight jeans should fit. I’m deciding between two sizes. Thanks for any help you can give me.

Megan Kristel

Wednesday 22nd of September 2021

These aren't really "straight" in the traditional sense so you should still feel them on the body, they are just not skin tight like a super stretchy skinny jean or jegging I hope that helps!


Wednesday 22nd of September 2021

Thanks for that great post & outfit idea! I just purchased these boots! I would love to see more outfit ideas incorporating this new style of boot!

Megan Kristel

Wednesday 22nd of September 2021

Absolutely! You'll see them featured throughout the season!

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