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Britney Spears Style Breakdown: What’s Right, What’s Wrong, and How to Fix It

Britney Spears at the 2011 VMAs
Jason Merritt, Getty Images

Newly-single lady Britney Spears has had more style misses than hits, and now that she’s in her 30s and has two kids, she can no longer chalk up mistakes like micro-minis and too-tight tops on being the pop tart she once was.

She was at the height of her Lolita powers years ago, but that phase has faded into the rear view. It’s time to dress more appropriately — and keep the sexy.

In the interest of brevity, we’ve limited our style assessment from 2008 through today (or we’d be here all day with the “What’s Wrong” part).

Brit looked the best she had in a long time at the 2011 VMAs with full, wavy blonde hair, soft and nude makeup and a sparkly mini by Moschino. But two days later, she was back to the sloppy ponytail and just-misses-the-mark colorblocked outfit (which you’ll see later in this piece).

Britney Spears at the 2011 VMAs
Jason Merritt, Getty Images

Her current look of heavy bangs is too extension-y. It looks fake and uneven. The makeup is also too thick, aging her as it settles into the finest of lines. She can get back to her VMAs self with just a little adjustment here and there.

Britney Spears
Frazer Harrison, Getty Images

What’s Right:

Pretty much everything here is right. At the time we thought the patent leather booties were wrong — we were thinking strappy heels would have upped the overall sexiness — we now realize Brit has psoriasis, so these were actually a smart choice to cover up scaly skin.

Britney Spears at the 2011 VMAs
Jason Merritt, Getty Images

She also looked pulled together at ‘X Factor’ auditions in an LBD with strappy heels and an angled blonde bob. The cut and color are appropriate for a woman who is a pop diva and a mom of two.

Britney Spears
Jason Arthurs, Getty Images

This is Brit at her sexiest in black Cavalli, which she wore to the 2009 Teen Choice Awards (notice her predilection for black and LBDs). It’s incredibly short, but paired with her long blonde locks and heels, it’s polished and put together, which is not often the case with her.

While we’d suggest she lengthen the hem now that she’s over 30, the styling here is right on.

Britney Spears in Black Cavalli
Jason Merritt, Getty Images

This gold frock is short with its hem but long-sleeved, and it was sexy because it didn’t expose too much skin. Except it did spotlight Brit’s psoriasis.

Britney Spears in Gold
Tim Mosenfelder, Getty Images

When she performed with Madonna at Dodgers stadium in 2008, she showed she was not quite a girl anymore, but almost a woman. The styling and the volume is what keeps this look fresh.

Britney Spears
Kevin Winter, Getty Images

What’s Wrong:

She was colorblocked in green and black in London, right after the 2011 VMAs. The dress is on-point with still-current trends, but the booties weigh it down, as does her sloppy hairstyle.

With the right styling, such as t-strap or ankle-strap pumps and a sleeker updo, this look would have landed in a different column. We understand that she has a skin condition, but you can always cover that in other ways, as opposed to clunky clodhoppers.

Britney Spears in Colorblock
Danny Martindale, Getty Images

At the 2010 Grammys, this sheer Dolce & Gabbana dress with a bodysuit is totally too casual and cheap-looking for this event. The chocolate brown locks are a nice, softening touch, but Brit’s better as a blonde. There’s too much going on with the fishnets and the studded heels.

Britney Spears in Dolce & Gabbana
Christopher Polk, Getty Images

Brit Brit wore this too-tight leather dress by Christopher Kane during the waning days of her stint on ‘X Factor.’ Her girls were popping out all over the place, and it looks like she nabbed this frock from the sale rack at Forever 21. She looks uncomfortable in it, too — see her posture? It’s stiff and unnatural. The maroon strappy Prada heels are bangin’, though.

Britney Spears in Christopher Kane
Imeh Akpanudosen, Getty Images

This silvery and white Halston sack she wore last year does nothing for her. It’s just fabric thrown on her body. It’s matronly and has no silhouette.

Britney Spears in Halston
Michael Kovac, Getty Images

Another “why, why, why?” moment happened when she donned this pantsuit during ‘X Factor.’ The tipped shoes make it look like black socks with white shoes. It’s a church outfit for a grandmother. No times 10. Brit, come on.

Britney Spears
Frazer Harrison, Getty Images

This hot pink Herve Leger bandage dress would be a hit if not for the overpowering clunky black boots. They don’t go. Again, we’re sympathetic to her psoriasis, but still … it’s not an excuse. She should match her dress to the shoes if the skin issues and concealing them are the deciding factor on what to wear.

Britney Spears in Herve Leger
Frazer Harrison, Getty Images

You can see her psoriasis below, which leaves us wondering if a little theater makeup could do the trick. We hate to pile on here, but what, no pedi?

Britney Spears' Psoriasis
Jason Merritt, Getty Images

How to Fix It:

She doesn’t need to go back to this…

Britney Spears
Gabe Palacio, Getty Images

Or this …

Britney Spears
Kevin Winter, Getty Images

But she can try more of this, like the silver Versace mini she wore to the 2008 VMAs. It’s in Brit’s wheelhouse, and it’s what she does get right. The dress and shoes are well-paired, and she’s pulled together.

Britney Spears in Versace
Frederick M. Brown, Getty Images

Her habit of hiding her skin condition with booties isn’t an awful one, as long as the styling is right. That’s what any fashion mag would suggest to an Average Jane reader, since Brit is battling a common problem.

But the shoes and dress must work in concert, and so many times with Brit, they don’t. Lots of happy mediums would up her style factor on so many levels. The basics are there. She just needs to implement a few fashion rules consistently.

See the Emma Stone Style Breakdown

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