How To Wear Black Flares to Allll The Parties


I love a killer all-black look.  Especially for the holidays.  All black is slimming, I can drink red wine without fear, and it’s easy to find shoes to match.  Holla.

But the downside is…boredom.  Especially during this shiny, glittery time of year, all-black outfits are often second-best.  Like my top choice was too cold/too complicated/needed a different bra…okfine.  Black pants it is.  However, there are a few ways to glam your black and make it a prime choice for holiday parties.  Mixing textures (like lace, velvet, faux-fur or shine, for example) is one option…but my current fav is to make an all-black outfit modern with dramatic silhouettes.

Namely, high-rise flares and an show-stopping top.








Add a glitzy bag, a little bling, and voila!  (And don’t forget the right bra.)







Outfit Details

top  – Flynn Skye Leah Top (size xs for reference)

pantsCitizens Fleetwood High Rise Flares (suuuper soft and stretchy – size 24 for reference)…we also LOVE Madewell’s flea market flares, also at Nordstrom (see Scotti in them here)

shoes – last year’s Vince Camuto – here’s similar

braFree People Lace Halter Bra

earringssimilar (more edited options in the Jewelry Shop)

bag – vintage, but we rounded up a bunch of similar pieces in the Evening bag shop


Shop Dramatic Black Tops


Gang, I’m always on the lookout for really special, interesting tops.  If you find some, let us (all) know!





  1. Is it just me or do these flares give you more “back”, if you know what I mean ;)…I have a boyish figure and could use some help in that department. I might be trying on a pair very soon!!!

  2. I’d call that the “wrong bra” – you should not be seeing your clasp on a backless shirt! And add a belt maybe? Those jeans just look too rough to be considered dressy. It’s not working for me. Close, but no cigar.

    • Ouch, Holly! Santa just added you to his naughty list. 🙂 Clasps aren’t a fashion no-no. Shoot, look at any current sports bra – clasps runamuck. The lace detail on S’s bra adds a gorgeous element to a fantastically simple outfit. Remember those hideous clear bra straps everyone was running around in?! Ugh, so terrible. This lace bra with clasp is elegant and stylish with the right amount of sexy sprinkled on top.

    • Hm, I don’t think she said the black flares were dressy. She talks about adding some glam to the outfit, but to me at least, ‘glam’ and ‘dressy’ don’t always have to go together. This type of outfit makes me think of Anjelica Huston in the 70’s — she often wore jeans, and always managed to look glamorous, yet casual and cool at the same time.

  3. I have been following this blog for several years and have never left a comment but after seeing the (last fairly) unkind comment I felt I just had to reply. Shana – I love the way you put things together in an unexpected and not-so-perfect way that makes it totally your own. I come to your blog often for inspiration and I think you look absolutely fantastic. What is perfect about this outfit is that it is sexy in a not-trying-to hard way. Adding a belt, dressier pants and a hidden bra as suggested would make it totally predictable and look like something one of the Real Housewives would wear. In fact I bought the pants, top AND bra last night (though not sure it is going to look as awesome on me!).

  4. This is a look after my own heart. Love, love, love it. The jeans, the bra, the top, the clutch — the whole look is perfection! You look freaking amazing.

    Parties in my town (Minneapolis) tend to be on the casual-cool end of the dressiness spectrum, and I can’t wait to re-create this. Like Vicki said above, it’s “sexy in a not-trying-too hard way,” which to me, is always the goal.

  5. Am I the only one who won’t be attending a single fancy dress holiday party? My office doesn’t do anything and my family is (unfortunately) super casual. SIGH. That’s the rocky mountain west for you I guess. I perennially suffer from “all dressed up and no place to go”.

      • Why not dress for yourself?! I was talking with a confident woman who dresses up for her holiday party, full on 4-inch heels and perfect little back dress, while all others dress in jeans. It’s a memorable, enjoyable process for her. Why not?

  6. You look so gorgeous and sexy!! I am so incredibly jealous of this top – my soon to be nursing boobs will be ungodly huge for the next year or so. Love my kiddos but miss having boobs I could call totally my own!! Any advice from Cams on rocking a super maternity look to holiday parties?!


  7. I have been obsessing over the black flares from Madewell and finally bought a pair…they arrived this evening…and I am so sad, they are short! Any recommendations for longer black flares? I am 5’8″ and bought the size 25. They are actually short enough that I don’t think I can even wear flats :/.

      • Oh no!! Christa – the same thing happened to Scotti, but we were in a Madewell store. They were insanely short, and she just grabbed another pair (of the SAME SIZE) and they were much longer. We just thought the shorts ones were a one-off, but maybe they’re having trouble with a little quality control.

        Have you guys tried Express’ mid-rise sailor jeans? They’re another of Scotti’s favorites, and come in short, regular and long inseams:

        • I haven’t! They don’t seem to have the mid-rise sailor jeans in black denim right now, though. 🙁

          I did find a couple of other potential options, though! Paige Denim ‘Bell Canyon’ High Rise Flare jeans in Black Shadow, which have a 35.5″ inseam (which still means super-low heels for me) — they’re at Nordstrom:

          Also, The Limited has some that aren’t quite as nice, but they’re waaaaaay less expensive:

          • Have you looked at Blank NYC flares? They are fairly long – I am 5’7″ and need to wear 3″ heels with them. Although I guess that still leaves you an inch short…math!

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