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How I Plan to Get Dressed This Winter
11.22.17

In partnership with MatchesFashion.com

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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