Style Challenge: Making Menswear Glam (But Wearable)

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So…’s style challenge week!  The week where we’re each challenged to try out something outside of our comfort zone…but in a way that feels authentic, not costume-y.

My style challenge?  Menswear.   No problem.  Immediately, this is the image that pops into my head:

Photo Credit: Harpers Bazaar

I mean, easy, right?  Menswear, got it.  Buuuut then the TME team clarified.  “We’re not talking about the low-cut blazer without a bra or blazer-as-a-dress thing, either, Scotti.”  Dammit.  Ok, so . . . like Shana, I had to turn to Pinterest for some help.  I started out with the idea of a slouchy blazer and loafers with boyfriend jeans.  There are SO many cute photos of this outfit all over Pinterest . . . BUT.  The problem was my body shape.  I’m definitely curvy . . . smaller waist with bigger hips and a booty and a slouchy blazer and slouchy jeans just made me look bigger.  So the hunt continued.  Then I found these pants.  So ridiculously comfortable (like wearing pjs outside) and surprisingly flattering.

Because the pants were slouchy, I needed a top that was a little more form-fitting so I reached for one of my favorite sweaters and paired it with a slim button up.  The bowtie was Zack’s idea . . . I thought it was going to look ridiculous, but I actually liked it!

The shoes . . . I just couldn’t do the loafers, guys.  I have yet to find a pair that are super comfortable that don’t make my feet look a mile long.  I went with some sexy pumps.  Gotta be true to your own style, right?  If you guys have some sexy-yet-comfortable loafer recommendations, let me know!

I wanted to try out this hair trend of layering bobby pins . . . it’s obviously messier than it needs to be, but I think I like it?  Maybe if I got some bobby pins that were a little more interesting . . .


Chambray Shirt: Available in regular and petite sizes.  I also love this  Fitted Boyfriend Oxford that’s also available in white and regular, tall and petite sizes for the perfect fit.

Merino Wool Sweater: A staple of my closet, this sweater comes in a ton of colors and regular or petite sizing.  Looks equally great with jeans, pants or skirts.  I actually wear this a lot with my sequin leggings . . . it calms down the look a bit.

Ankle Tie Pants: These have been restocked after selling out and are SUPER comfy.  I also really like these Tie Waist pants that come in navy, black and olive green.

Nine West d’Orsay Pumps (similar): These Ankle Strap Pumps come in a ton of colors, these Steve Madden pumps have a block heel for comfort and I love the tie on these pumps.

Bowtie: This was actually Zack’s bowtie AND his idea for me to wear it.  I thought it was going to look ridiculous, but I actually liked it!  I think it looked surprisingly feminine . . . almost like a necklace.





About Author

Meet Scotti, the contributor with our most-loved beauty advice. When Scotti's not giving us the scoop on the latest products and techniques she's dishing out some of TME's most loved looks. It's not easy to look so cute in the U.P. of Michigan (i.e. crazy cold and snow) but she always makes it happen.

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    • Thank you! So I ordered my usual size (medium) in the pants . . . there weren’t as many reviews when I ordered them and I’m glad because lots of people are saying they run big. I’m sure on people without larger hips/booties they might be big, but I loved that they kind of sat above my hips and DIDN’T give me muffin top. Super comfy.

  1. This look is wonderful! And such a good call not going with a pair of loafers, the heels really add a fun element to this look! Great job

  2. Looks really great! Nice, classic pieces and fairly simple alone, but put together, it has a definite WOW factor! Well done!

  3. I like it! You guys are doing such an amazing job taking on new looks but keeping them true to YOUR STYLE. I can’t wait to see more! I love this idea of encouraging us to try something new but still keeping her to our STYLE/LOOK. Perfect.

    • Thanks! Yup – that’s exactly what this challenge was all about. And it was definitely a challenge for each of us! 🙂

  4. Cute outfit. Wish you had done men inspired shoes since your sister wasn’t allowed to do over the knee boots! 😉 I think you need a redo! 😉

  5. First time commenter here. This outfit is totally up my alley. I’m curvy, too (small waist, big hips, big legs and I’ve got booty, too), and I can’t believe these pants would work.. but obviously they do! Thank you for showing styles for us curvier girls. Would love to know what size you got.

    • I got a size medium! True to size, but the reviewers said they ran big . . . I didn’t find that to be the case, but I guess I didn’t really try on the small either. I just liked that they were slouchy and comfy and didn’t dig in at the waist band (a problem I usually have). So glad you liked it!

  6. I LOVE menswear and feel so comfortable in it. I need a new pair of loafer/flat/brogues and have been looking at Everlane’s loafers since the toe is a bit more pointed but not overly so and also I love high boots with a kiltie tassel (is that a thing?) and lace ups in front. What about cut out oxfords? It would break up the whole foot-covering-ness of an oxford and would skew a little sexier…

  7. You look beautiful! This is one of my favorite looks I’ve seen on you! Makes me want to copy this whole outfit. I’m a curvy girl too, especially after two kids the curves are…padded. Thank you!

  8. I tried this out today & loved it! Used a smaller bowtie (my son’s) and really thought it worked nicely. Unfortunately, my sweater wasn’t fitted enough and I had to abandon parts of the outfit. Definitely need the fitted top to balance out the loose jogger type pants. The D’Orsay pumps were spot on perfect.

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