How I’m Making Baggy Jeans Sexy

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Ok, maybe this one should be called “How I’m Making Baggy Jeans Sexier.” Because IMO, baggy jeans, in and of themselves are just…not…sexy. I mean, they’re fine…but like…not what I would typically choose.

BUT. They are super comfortable and I’m well aware that they’re not going anywhere anytime soon. So let’s work on making this trend work for me.

Tip #1: I Only Wear Heels With Baggy Jeans

First off, I have to address the shoe issue I have with baggy jeans. I LOVE the way they look with heels…they’re leg-lengthening and slimming and since most of my boots have a 3″ heel, I have lots of options to pair them with. IF I wanted to wear them with sneakers, I would absolutely need to get them hemmed.

I’m thinking more like this:

jeans | top | cami | belt | bag | boots

Instead of this:

jeans | t-shirt | similar sneakers (not that it matters)

Exhibit A: Sneakers vs. Heeled Boots

At the length these jeans are right now, they look a bit ridiculous over sneakers (not to mention the fact that they drag on the ground). But since I don’t really love the way they look with sneakers (and DO love the leg-lengthening look with heels), I’m choosing not to hem them. So all of the looks here are with heels…just FYI.

jeans (more sizes here) | similar sweater

Exhibit B: Moon Boots vs. Sorel Wedges

But just for good measure, I had to try one more flat option. I honestly thought Moon Boots would look SO cute with these since the legs are so wide! I thought they’d just fall over the top and kind of look casually slouchy in the best way. Obviously I was wrong…and although they may actually look cute if they were shortened, I’m going to stick with my Sorel Wedges if I want to wear warm boots with my baggy jeans.

jeans (more sizes here) | moon boots (left) | similar sweater | similar wedges


Tip #2: Cropped/Shorter Sweaters Work Best

Ok, so what goes on top? After trying multiple looks and seeing what works and what doesn’t, my main “rule” (and I use that word super lightly because I hate rules when it comes to fashion) is to stick with anything that puts the accent on the waist. So tops that are shorter or tighter or can be tucked in…that’s what I like. My favorite way to wear them (at least while it’s still cold out) is with cropped sweaters.

jeans (more sizes here) | sweater (also at Nordstrom)

Not to be confused with crop tops (although those would look super cute if you’re into them!), sweaters that are cropped enough to show off the waist look best, IMO. This way curves are visible and not hidden under longer hemlines. And I almost always wear them over this Hanro bra cami so I’m not flashing any skin if they come up as I move (and it adds a layer for warmth–cold air isn’t just blowing all over my belly).

jeans (more sizes here) | similar wrap sweater (left) | cardigan (right)


Tip #3: Show Off the Waist

Although cropped sweaters were my go-to, there are a bunch of ways to style other tops to make them work with baggy jeans. The same “rule” applies, though – make sure that waist is visible!

Exhibit A: A Black V-Neck Top

Although the look on the left is fine, the look on the right is just a bit…better (or at least more my style). It puts the emphasis on my waist and doesn’t bunch up and look sloppy. I found that bodysuits almost always look better with baggier jeans because they lay flat on the sides.

jeans (more sizes here) | similar v-neck sweater | similar bodysuit

Exhibit B: A Turtleneck Sweater

When it comes to sweaters that are a bit longer, tucking in the bottom makes a huge difference. I don’t just shove it all into the jeans, though…all that extra fabric doesn’t look great tucked underneath. Instead, I just grab some of the fabric, twist it a bit, and tuck it in to the side or the back in order to show off the waist.

jeans (more sizes here) | similar sweater (cashmere over 50% off!) | similar boots

Exhibit C: An Oversized Button Up

The look on the left isn’t bad, it’s just not really my style. With an oversized top like this, I want to find a way to create shape…so I leave it unbuttoned, wrap the sides over each other, tuck in, and fasten the buttons that line up. I like being able to wear oversized shirts in multiple ways–and this trick would work with most of them!

jeans (more sizes here) | button up (m)

Exhibit D: A Short Sleeve Top

Again, there’s nothing wrong with the look on the left (in fact Shana loves it), but I prefer a tighter, more fitted t-shirt that shows off curves and the waistline. This one from Anthro is so good because of that shiny fabric and that drapes so well. It’s not skin-tight, but still shows off shape…and comes in a bunch of colors. (Although the t-shirt on the left is one of my favorites…but I usually pair it with tighter flares like these or leather pants!)

jeans (more sizes here) | t-shirt (s, left) | boots | t-shirt (xs, right)


I know not all fashion trends work for everyone, but I actually enjoy trying them out to see if I can make them work for me, my body shape, and my style. What do you guys think? Are you loving or hating the baggy jean trend?

XOXO,

Scotti