In Partnership With
How I Plan to Get Dressed This Winter

In partnership with

You may remember that nearly two years ago, Man Repeller partnered with MATCHESFASHION to bring you a regular feature of theirs. I like to call said feature the most seamless, remote personal shopping experience ever executed on the Internet, but they simply call it “Shop With.” Essentially, they identify people who they believe maintain good style and then ask them to style a number of looks for their site that culminate in a curated shop. These looks are then displayed, promoted and arranged for an easy shopping experience so that you, the reader, the user, the consumer, the champion!, can glean inspiration and maybe a pair of sunglasses that you don’t want but really need (see what I did there?). The first time we did this I paired striped shirts with metallic robes and airy pants, and black tie gowns with sneakers and even tried to make a case for non-prescription eyeglasses with earrings and a beach dress in the middle of February, which probably doesn’t sound all that different from the multitude of cases I would make in present day but guess what? It is different! And you can know this to be sure because here we are, about to embark on my second Shop With feature and there is nary a robe coat in sight. Not one!

Not. Even. One. What you can expect includes:

Patent leather pea coats and layers of floral print

It is still technically warm enough to eschew tights, so we are going to do that until we’ve reached freezing point, and if a pair of tassel loafers and plain white socks want to come along for the ride? That’s just fine. If you’re wondering about where you should wear this outfit, I urge you to consider what you do all day because frankly, I can’t think of a single scenario save for a cycling class where this look doesn’t seamlessly fit in with the quotidian encounters of your day.

More patent leather (pleather, really)! But in trench form and with pants

The irony of a trench coat that is not actually water resistant never gets lost on me; it’s one of my favorite functions of what I like to call “decorative utility wear,” but at least this coat maintains plackets that will protect your chest from a soak should the water come. What you don’t see, really, is that I’m simply wearing a long sleeve black t-shirt underneath the jacket, paired with these elastic waistband pants by The Row. This just goes to show that a coat can do all the talking for your outfit, but if you’re willing to let them, shoes make for a good microphone too. If I were you, I’d wear this to work on a casual Friday and if your office is stuck up just remove the jacket the moment you get in.

An equestrian disco ball, anyone?

I don’t know what’s gotten into me, but suddenly I am dying to look like I ride horses even though I have very little interest in actually, you know, riding horses. Maybe it’s because I have this picture of Princess Diana etched into my brain, or maybe the boots offering that is currently out there promote a lifestyle that I don’t live, but am very much willing to buy into. I can’t know for sure, but here’s the important part of this: I never like looking too literal, which is why there is a sequined dress masquerading as a skirt on my person. You don’t ride horses in sequins! Or do you? The headband is optional, but why not embrace the extra accessory?

The lady of leisure I always aspire to be

To hell with work! I’m staying in today. Nay, I’m going out, I’m going out to read magazines and drink caffeinated beverages and wear sunglasses that are unnecessary given the day’s haze. Or at least that’s what my outfit says. In reality, I’m getting a bottle of water because I’m parched between meetings and have at least four more obligations on my calendar for the rest of the day. Have I mentioned it’s 4 p.m.? I haven’t had a chance to eat quite yet, but I’ve just been so busy crunching them damn numbers. My life is like a shuttle service: home to office, office to home. Look like a lady of leisure, I always say. It doesn’t mean you have to be one. Pajamas are an easy suggestion; satin mules, however, are a necessity.

That about sums up everything I have to say in about four of the 13 looks styled for this feature. Don’t be a menace, though, and definitely don’t miss the rest of the outfits. You can ensure a thorough perusal by clicking this link. Just please come back because I need to know what you think.

Photos by Edith Young.

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  • Fransjejohanna

    Ugh I love all these outfits 🦄🦄❤️

  • Aida Schooler

    it is a pet peeve of mine when there is ornamentation on the front and then the back is ignored.the sequin skirt looks cheap but i bet it is not.

    • Emma Charlotte Pratt

      would usually agree, but also a certain degree of practicality to not having to sit on (and subsequently ruin) sequins as you would if they were also on the back.

    • lateshift

      This is a thing I’ve often thought – but sometimes, especially if you position it a certain way (which you can do with skirts…not so much with half-sequined shirts), it can look intentional – like it’s highlighting the area of ornamentation, when covering the whole thing might be overkill. I don’t know. anyway, that’s what it looks like here to me. I don’t hate it. and of course the outfit as a whole is 👍)

      • Aida Schooler

        i like this “moving the skirt” idea. For me the back fabric reminded me of when i shopped at Limited Too, which brought back very polyester memories. Now though i am imagining a sequin front skirt but instead of cotton/poly doing a thick wool or silk, a more intentional fabric.

  • Setare IR

    I’m sooo obsessed with the second one!! wish I had a pleather trench like that! (ps. I also find it ironic that trench coat is not water resistant!!! 😐

  • Chalisse Burrell

    All of these outfits give me life! Amazing writing as usual. Leandra your killing me!!!!

  • Áine Hegarty

    On: making a case for non-prescription eyeglasses, I always think they look so cute but am afraid of being called out as a phony. Anyone else?!

    • Just do it.

      PS. I once had a client who had laser eye surgery to correct her -10.00 prescription and came right back to get her glasses redone with plano lenses because they finally looked cool.

    • This (kinda) happened to me! I have to wear glasses but look less than great and more like a mole when I wear them due to the high strength of the prescription. I found a really cute pair of eyeglasses and was wearing them with my contacts when I was in a group of friends and one of them kept insisting that she try them on to see how bad my eyes were(?). Like, she wouldn’t stop even when I was annoyed. I finally had to admit in front of the whole group that they were fakes.

      But I lived and now have told. 🙂 I think most people are okay with it even if they’re a little baffled.

    • Jessica Murphy

      Yes, only with clip-on earrings. Anyone?? As someone with revirginized lobes, I thought I’d look childish or be judged for wearing the equivalent of a training bra on my ears. But there are SO many legit chic ones out there. I just swooped a couple pairs at the Net sale, planning to clip it, clip it good this winter.

  • ALL ABOUT THESE OUTFITS, LEANDRA!!! Seriously, all killer.

  • Maddy

    Who makes the headband??!! <33

  • Hankaf

    Patent leather is a yes from me!!

  • Lady of Leisure ! Too bad I am currently one, working on master’s thesis at home. Inspired by this, maybe I’ll slip into my golden sequinned Valentino mules tomorrow and parade around the house.

  • Jak77

    Leandra you look more you than ever!!!! Keep it up girlie!

  • You have awesome ideas for winters. Sure, going to follow the same. Since it is winter so I am thinking of buying a trench coat with jeans and long boots.

  • Olivia Black

    Love love love that skirt/prada jacket/riding boots combo! I’ve always wanted to be a horse girl when I was little–my oldest/longest-standing fantasy/daydream is of me riding a horse in a large, open hilly space like in Princess Diaries or something. I think the fantasy has followed me into fashion–I love the fresh-off-the-horse look–riding pants, boots, the works. I’ve also been trying to figure out how to wear my knee-high boots without looking very.. well . suburban. They are so cute here with the sequined skirt !! <3 Very inspiring!!

  • Hannah Warner

    The floral look is so so good.