How Can I Wear This?! (Mystery Menswear Styling Challenge)

Throughout our lives, we gradually accumulate things, including clothes and accessories, that were once interesting, but we often forget about and hardly wear anymore. Today, as a challenge, we take some of these items from our closet and try to put them together in outfits within a limited time!

*Note: Be sure to watch today’s video to understand the nuances of the styling challenge!

Video Transcript [Lightly Edited for Clarity]:

Sven Raphael Schneider: Welcome back to the Gentleman’s Gazette. In today’s video, I’ll be put to the test with mystery items from my wardrobe that I then have to take and put together an outfit without spending a lot of time.

My wife and business partner, Teresa, picked out the items. Chris is going to hand them to me, film me, and I’ll just talk about the item – where I found it, how I like to style it, or, if I don’t have an idea, how I decide to style it – and so you can see how long it takes me, how I do it, and why I do it. I’ve been collecting menswear since the year 2000.

So, over time, you amass quite a few things and, with the clothes being in different spots, it’s easy to miss something or hide something underneath an overcoat. I’m sure you have some items that haven’t seen the light of day in a while too.

So, Chris on the camera is going to hand me items out of an ominous IKEA bag, and I swear I have not seen these items before. No, just kidding. I honestly have not seen these items before. Well, I probably have because I bought them at one point in time. But I don’t know what’s going to happen in the video today.

1. Wegener Bavarian Velour Hat

First item. Wow! Okay. Short-brimmed hat with this kind of green ribbon. It has a very kind of alpine-style feel to me. Maybe a tracht, which is kind of a traditional German way of clothing.

This hat is from Wegener and it’s called “Bavarian.” It has also what is called a “velour finish,” which truly feels like a nice velour or velvet. But, as you know, high-quality hats are made from hair, usually like rabbit hair or beaver hair. And so, this finish is hard to find these days and, therefore, very unusual and, because of that, I bought that hat. I couldn’t tell you how old it is exactly. But, based on the tag inside the head, I would guess probably 70s.

With my big ears, this kind of short brim is not ideal, and, if you want to learn more about how we can find the perfect hat shape for your face shape, check out this video here.

Now, without further ado, I’m gonna pick my first outfit.

Outfit #1

All right. I came back here still putting on my tie.

Now, this hat I got from, I think, a guy named Steve Heck, who is a collector of German and Austrian hats – particularly, vintage hats. He has a large collection of these high-quality hats and, you know, he travels to hat factories in Třinec, for example, in Czech Republic, and just tries to learn more about it and it’s his hobby.

So, I met him once at his home and, you know, he has more hats than he can wear, also in sizes that he doesn’t wear, and so I just bought a bunch from him and this one included. I can’t remember how much I paid for it, but I’m sure he made me a very fair price.

Whenever you see hat videos here in Gentleman’s Gazette, Steve often assists and helps us with specific details about the history because his knowledge in the area is just second to none. 

How does that look? Tying the tie without the mirror. Good? All right.

So, in this outfit, of course, I wear this Wegener Bavarian velour hat and it has this kind of elements of chartreuse and green, so I decided to pair it with a green corduroy jacket and vest. 

My pants are contrasting chinos in a grayish-green, I think from Polo Ralph Lauren. This ensemble was custom-made. Not for me though.

A shirt with a button-down collar in bold brown and wine stripes. So, the corduroy has these fine stripe, textured look even though it’s solid so, having those bold stripes, it’s an obvious contrast, but it’s brown like the hat.

And the tie then is the Fort Belvedere silk knit tie in brown and white, has this kind of changeant effect. But, it works really well with a shirt. But, again, it has a much smaller pattern in the shirt. So, pattern-wise, it all works. Color-wise, it all harmonizes.

My pocket square is brown. I wanted something brown. It has some blue. There’s no really other blue in the outfit but it’s okay. My boutonniere is a green and white lotus flower, so you can see green-white, brown-white. It all kind of tries to tie things together.

I think, overall, green is one of the most underrated colors in menswear and, if you want to learn more why, check out our guide.

Now, I might as well just wear a pair of dark brown, suede Chelsea boots. I think they would have looked very nice with it, but I had easier access to my green derby shoes from Carlos Santos. Here, they’re with a contrasting pair of light brown shoelaces. There’s no light brown anywhere else in the outfit, so I could easily change that out. But, for the sake of time, I didn’t do that.

Last but not least, my socks. I just left them on from the previous outfit. There are these gray and white, two-tone solids and, as is the case with all two-tone solids, they’re very easy to combine. So, even though there’s no specific gray there, it works well with the pants and there’s still some contrast between the shoes and it’s not too loud and, overall, a harmonious highly unusual outfit.

Now, obviously, I color-coded this outfit with a hat – tones of brown and green. But, I also try to bring in the different textures. For example, this is velour or velvet. Corduroy is made the exact same way as velvet, so it has that changeant effect in the light. So, my hat is like velour or velvet, then I have the intermediate corduroy, and then a transition to the cotton twill of the chino.

Now, for my footwear, as I said, I could have gone with these suede Chelsea boots or I could have gotten away with a pair of contrasting, dark brown, woven leather Chelsea boots or any other type of dark, contrasting, leather boots. And because the footwear is so far away from your head, it doesn’t have to match a hundred percent because it will look consistent, contrasting, and good, even though the color is not a hundred percent.

2. Chartreuse Green Cashmere Sweater

All right. Next up, is a chartreuse-green cashmere sweater. Now, keep in mind, I have to go back. I have to undress and put it back on.

This one, I think, I got at an estate sale. It was from a person who was really into Ralph Lauren, so he had tons of Ralph Lauren stuff – sweaters and all kinds of stuff. And I saw this and I was like, “Hm. It’s interesting. It’s a crew neck,” which I usually don’t wear because I like to wear ties and have that V-neck sweater. But, it’s cashmere and it’s chartreuse, so it’s a bold color.

So, let’s see what I’ll come up with.

Outfit #2

Okay. So, with this chartreuse cashmere sweater, I decided to choose something contrasting. Now, I found this beautiful, heavy tweed, windowpane, navy jacket. It’s an old Hemrajani. It has these patch pockets. It’s a side-vented jacket that is normally very dark because the windowpane, it’s very bold. So, I also had this bold chartreuse sweater so I was like, “Why not?” 

So, for the shirt, I chose just a plain white shirt with barrel-button cuffs because of the sweater. I don’t like to wear it with cufflinks. You don’t see them anyways. Now, you can if that’s the only shirt you have. But, when in doubt, I always go with the button cuff.

Because it has the crew neck, a necktie is really hardly visible at all. So, if I wear a crew neck, which is hardly ever the case, I would opt for a bow tie. Here is this kind of off-white color that goes with the windowpane. It has a little green and blue in it just so it ties everything together. 

Of course, I don’t have a chartreuse bow tie, even though I have a chartreuse knit tie, but you don’t want a tone-on-tone, you want some contrast.

Instead of a pocket square, which I don’t have a chartreuse one, I opted for this edelweiss flower, which has this soft, velvety, kind of fuzzy touch and feel, which goes well with my jacket and the chartreuse sweater.

My slacks are cotton chinos in kind of a grayish blue, picking up the color of the jacket. It’s in a much smaller pattern, thus being very contrasting.

For my footwear, I chose some chukka boots, which are also bold but the color really matches the window pane, thus tying it all together. For my socks, I had a prototype pair of Fort Belvedere two-tone solid socks with chartreuse and gray. We decided not to make them because probably not that many people want chartreuse socks, but I still have it in my wardrobe and I wear them occasionally because, like all two-tone solids, they’re quite versatile, even though the color is out there.

3. 60s Inspired Madras Jacket + Mauve or Vintage Pink Shoelaces + Anemone Boutonniere

Alright, time for a new item or let’s say change the ante and Chris can give me three items now that I have to combine in one outfit. Obviously, not three pocket squares or three ties. Alright, some bold choices here.

First of all, kind of a madras jacket, very kind of 60s-inspired, bleeding madras. We have a guide on it on the website. You can check it out. And then, kind of these mauve pink or vintage pink shoelaces. These may be boot laces and then, a boutonniere. One of ours. I think it’s an anemone. I have so many. I don’t know them all by heart. But, one of our boutonnieres. It’s a little larger, but it picks up those tones of pink.

Let’s have a look.

Outfit #3

All right. So, I have this plain white shirt because this bold madras pattern is already loud enough. I chose this light blue mottled knit tie from Fort Belvedere as it picks up these kinds of tones of blue from the bleeding madras. I chose a pair of tan, silk-linen trousers from Polo Ralph Lauren because they pick up the color off the jacket and it’s a very lightweight summer trouser. 

And with the pink shoelaces, I figured it would look best with my pair of white bucks. They’re Oxfords and pick up the white in the shirt and the boutonniere flower.

Now, the boutonniere is so large. It’s way too large for this size of lapel. But, it’s a challenge, so I’m gonna wear it, and I’m gonna skip the pocket square. Otherwise, a white pocket square would definitely have worked well.

This madras jacket, I got at a local vintage store here; two blocks away from here. It was called Via’s Vintage. Unfortunately, they closed due to the pandemic. But, they always had interesting stuff. Oftentimes, I find, with vintage madras blazers, they’re all tight on top and, this one, I had altered. It has a center vent like most jackets from the 60s, but it is what it is. If I could choose it today, I’d go with side vents. But, you can’t always choose.

The boutonniere is this pale purple anemone. Because it has white in it, it’s very easy to combine with any type of white shirt.

The pink shoelaces have this nice vintage pink. It’s not over the top pink and bright pink, but it allows you to combine it with a range of different boots and shoes.

Here, because I already had the bold outfit on top. I decided to also go bold at the bottom, not necessarily something you have to do. Maybe a pair of loafers, even something in dark brown, for example, would have been just fine as well. But, of course, I had to use the shoelaces.

The socks are two-tone solids, kind of oatmeal and beige, which work with any type of lighter brown or tan trousers and slacks. You can see why I love those shadow-stripe or two-tone solids because they make it so easy to combine things on a whim.

Alright, Chris. This one was a little wacko with a big boutonniere. How about we do two different items this time? See what’s coming out of the big bag.

4. A Pair of Needlepoint Bowhill & Elliot Slippers + Suspenders with a Paisley Green & Range Pattern

Alright, a pair of needle-point Bowhill and Elliott Albert slippers and a pair of suspenders with a paisley, green and orange pattern.

These ones here, actually, I bought from Crowley Vintage. It’s a vintage store in Brooklyn owned by Sean Crowley, and he had these needlepoint ones. He had one in like gray and light blue, but they’re just a little too big so I went with these. And yeah, traditional English Bowhill and Elliott shoes.

These here, I got from an estate sale. I like going to estate sales of nice houses. And, sometimes, you go there and, you know, the person had 150 bow ties because they were a trial lawyer and then they also have these suspenders, and most people just don’t care for them.

So, I found that sometimes, if you go back on the last day of the sale, towards the end, you can ask the vendor, “Hey, you know, I’ll buy all these for 200 bucks.” This was one of those purchases where it was just a bunch of stuff and I was like, “Yep. I’ll take ’em.” It doesn’t even have a brand name on it. Just says “Made in the USA.”

Outfit #4

Now, there are certainly men who like to wear Albert slippers in public. I’m not one of those. To me, Albert slippers are a homey outfit, so I decided to wear something more relaxed and casual. 

Here, I have this soft kind of polo pique knit shirt. It’s cut like a shirt, but it’s a flexible material. Very casual. I also decided to pair it with my velvet, double-breasted, shawl-collar jacket because it is red and bold and complements the boldness of those green, black, and red Albert slippers.

When it comes to suspenders, most of the time, most people won’t even see them. It’s maybe your significant other or if you take your jacket off. Otherwise, they’re not so important in terms of pattern matching, but it can be cool to have a bold pair of suspenders if that is your style.

So, in order to pick up the red color of the shoes, I added a red boutonniere and a red knit tie. I skipped the pocket square again in order not to overload the ensemble.

The pants are part of a suit. It has a nice, bluish, pinpoint pattern. They don’t have a fishtail back. It’s a simple straight back, but they’re made for suspender buttons. I like wearing suspenders because they keep your pants at the right height. Your pants can be a little wider, looser; it doesn’t matter. Always stay the right height all day long. And so, that’s one reason to wear suspenders. 

For the socks, I chose a pair of gray and white two-tone solids. I could have chosen a navy one but because of the white and the sparkle, you don’t see the nuance between light gray or dark gray very much or black for that matter. I just wanted something with a bit of shine to contrast the pants and the Albert slipper without being too loud. I obviously didn’t have something that was exactly matching my pants, so that’s what I chose.

5. Ralph Lauren Orange Tie with Diamond Pattern

Alright, Chris. Last but not least. What do we get here? Okay. This is a Ralph Lauren Polo tie. Very kind of 90s. It has this kind of Wall Street power look. Bold. Has that classic, rotating diamond pattern. So, it’s a printed tie on woven silk, a very maximalist approach.

Outfit #5

At first, you might think, “Orange? What do I come up with orange?” But, frankly, it’s quite easy. Since there’s blue in the tie, it’s very easy to combine it with a navy blue blazer. Here, it’s one from Isaia with nice pewter buttons.

Went with a white shirt with a collar that’s not too spread and a pair of cufflinks, paired with a pair of gray trousers and orange and blue two-tone socks that pick up the color of the tie, and then combined with a pair of black, half boot Oxfords. Note the shoelaces are contrasting in gray, matching the trousers and the pewter buttons. Ties the overall outfit very well together. It’s very classic-looking, even though the tie is bold. 

Outfit #6

Alternatively, I could also wear it with a navy stripe suit. Here, it’s a double-breasted rope-stripe suit. Again, a Winchester shirt, so white collar, light blue body in a herringbone pattern, paired with a pinky ring and a gold tie bar, as well as cufflinks.

For the socks here, I chose a pair of orange and gray striped socks to pick up the orange. I think the previously shown orange and blue are much better with this tie. And the same pair of half-boots, black Oxfords here with black shoelaces, and you can see they look much more formal than with the contrasting great ones.

So, what do you think of this format? Did you like it? Obviously, the combinations were somewhat bobbled, but that’s because the pieces were somewhat unusual. Of course, there’s no outfit rundown because you saw the outfits already.

Which mystery menswear item from today’s challenge did you find most interesting stylistically? Let us know in the comments!