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Outfits in Real Life: Straight Jean Style

The war on skinny jeans continues, and, for the most part, I can’t get behind what is being offered as an alternative.

These oversized, wide-leg, or baggy jeans feel like men’s work pants from the 90s that they bought at Gap.

Nothing about them feels tailored or feminine. On the contrary, every style I have put on my 5’10 frame feels broad and masculine. 

Which, I don’t know about you, but that is not the look I’m going for.

Part of my job is to take current trends and find ways to make them accessible and appropriate for our readers.

And over the last few weeks, I’ve heard from many of you telling me that skinny jean alternatives also do nothing for your body shape.

So in today’s Outfits in Real Life, I’m sharing the one style that has helped me bridge the gap between a skinny and a straight leg jean. 

And fear not because I do not want you to get rid of those skinny jeans, in fact, I’m sharing some ways to update them next week.

Outfits in Real Life: Straight Leg Style

For everyone new, Outfits in Real Life is our weekly series in which I share my outfits featuring items we recently recommended. 

I share photos entirely unfiltered, with zero photoshop and no airbrushing. I’m not working professional hair and makeup – clearly, and no one is steaming my clothes. I’m getting dressed amid chaos like everyone else to reinforce the point that you can pull together classic and chic outfits with a bit of guidance from The Well Dressed Life. 😉

As always our content and the items we recommend are not sponsored or gifted in any way. I buy everything myself so I can give advice with no strings attached. 

This is an easy, throw-on-and-go-about-your-day outfit. It’s comfortable, casual and effortless while maintaining the tailored classic feel we all love.

And most of the pieces are very affordable.

I usually would have worn a pair of dark skinny jeans with this, but I’m trying with the straight-leg crowd, I really am.

So after buying and trying on more pairs than I can remember, I landed on this inexpensive pair from Old Navy as my favorite.

The big difference between these and a skinny is that they do not grip your ankles. So you get a more relaxed fit.

I like them and highly recommend them if you are in the same predicament.

And they are almost always on sale for under $40; today, they are 50% off. The Mid Rise Slim Straight Leg Jean bridges the gap between a skinny and an actual straight leg.

I’m wearing the medium wash and also have them in the dark wash, which are nice to have on hand if you want to feel a little more polished. 

I paired them with this Quarter-Zip Sweater, also from Old Navy and one of our best sellers for the month.

Above, I’m wearing the white heather, but I have it in every color. It is soft, not itchy, and it has a lovely hand that drapes well. 

It’s also 50% off today. 

Then, I added one of my favorite pairs of sneakers, the Veja Campo Leather Sneakers.

I’m wearing the white and tan, which are unfortunately sold out, but the grey combo is still available and equally versatile. It would actually work better in this outfit:) .

You want your sneakers to have a low profile to work with this length and style of the jeans. 

And if you need a nice no-show sock I’m wearing these from Amazon, 8 pairs for $15. 

The rest is easy. 

Because I am overdue to get my hair done (going tomorrow!) I grabbed this wool baseball hat from Madewell, on sale for $17. I like that it’s an elevated basic and adds some texture. 

Also, I go nowhere without my Lululemon Belt Bag, which is chronically sold out online. Reviews claim that this $15 option from Amazon is a close dupe. 

Finally, I believe in having a capsule of jewelry you wear daily. It helps add your personality and makes it easy to accessorize. 

I find a lot of that jewelry on Amazon. These hoops are my hands down favorite

And, as you know, I love a wrist full of bracelets.

Some that I have are precious, but I have not problem layering in some affordable finds, like this two tone cuff, this love-bracelet dupe and my latest find, this gorgeous Swarovski Evil Eye Crystal Bangle that I found just last week. 

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

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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Outfits in Real Life: Straight Jean Style

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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Monday 24th of October 2022

Dear Megan! I was thrilled to read this post and immediately tried to order a pair. Tragically, Old navy does not ship overseas (Sweden). Please help a short curvy girl out! If maybe there is a kick flare that could perhaps work?


Wednesday 19th of October 2022

Thank you so much for this post. I’ve been struggling with the Jean trends so this was helpful. Would love to see how to wear ankle boots & even the higher ankle boots with the straight jeans. Thanks again.

Tracy Gray

Tuesday 18th of October 2022

Love the outfit and you look good! I maybe one of not many but I love my skinny jeans. Since I’m just 5’2 I feel like they give me a long leg look—crazy yes I know but I do love wearing them!


Tuesday 18th of October 2022

This cracked me up: ..."but I’m trying with the straight-leg crowd, I really am." I appreciate it - skinny jeans always made my legs look like sausages, even after I lost 30 lbs. I vote bootcut!


Tuesday 18th of October 2022

I just went to ON and found a straight leg that I love. Thank you for the suggestions! I love seeing your real pictures. You are such a help :)


Tuesday 18th of October 2022

Thank you for the inspiration and practical advice! Regarding fit, do straight leg pants have an 8” leg opening? Should they fall below the ankle bone (w/out touching top of sneaker?) Thanks!


Tuesday 18th of October 2022

Target has a great straight Jean (and inexpensive) in the universal threads brand. The mid rise straight comes in regular and short length and two washes. The lighter denim is 100% cotton (or close) so are a bit stiffer; I cut the hem off these. The darker wash has more stretch. Thank you for the amazing content!!

Megan Kristel

Tuesday 18th of October 2022

Great tip! Thanks!

Amy Hahn

Tuesday 18th of October 2022

Love this outfit - forgot I bought the sweater in your last What to Buy from Old Navy post! Traveling later this month and this looks cute and comfy for the long car ride! I search “Well” in my emails every morning so I can read your post. They are timely, practical and fun(ny) too! Thank you! I’m a PA girl too, living in Bucks County.

Megan Kristel

Tuesday 18th of October 2022

Thanks Amy!!!!! Hope you're traveling somewhere fun!


Tuesday 18th of October 2022

Hi Meg! I love your blog and read everything you put out. Can you tell me what socks you've found that work with those shoes? I don't like the super thin "liner" socks, but I can't find a sock of normal thickness that doesn't show for 1/2 an inch above my sneakers. I hope you have some good ideas. I keep trying socks and now I have dozens of socks that are ALL WRONG. :/


Saturday 22nd of October 2022

@Megan Kristel, Thanks!

Megan Kristel

Tuesday 18th of October 2022

YES! Thanks for reminding me I meant to add this to the article. I'm wearing these that I found on Amazon, 8 pairs for about $15. I think they are "normal" thickness, very comfortable and don't show :)