“I’ve had a good time! God, man, I rode around this country free as a bee.” (Jack Kerouac)

Let’s talk bicycle style! If you, like me, are new to loving bicycles, it can be a relief to realise that you don’t have to dress like you’re in the Tour de France! No, no. I will never — & you probably will never have to, either — pour myself into a pair of lycra bike-shorts, or wear a pair of those very ferocious-looking reflective sunglasses! For this, I am thankful.

It’s true that you can look just as cute on a bicycle as you do on two feet (if not moreso!), but I understand if you have some trepidation around the subject. I’m here to ease your fears! Here, then, is what I wear when I’m on a bike…

On hats, helmets, & not splitting your head open

Let’s begin at the top! As much as I value my hairstyle, I also value my brain. It sure would suck to fall off my bike & get my brain all over the pavement! So as soon as I got the phonecall that my bike had arrived, I went over to Adeline Adeline to pick up a Yakkay helmet.

Yakkay helmets are pretty fabulous. Instead of rocking regular old helmet style, they came up with the (genius!) idea of selling a helmet with interchangeable hats which you can slip over the top! BRILLIANT! I started off with a Paris black oilskin, which is super-cute while also being simple enough that it goes with practically any outfit. The selection at Adeline Adeline was a little on the slim side, but I was told they replenish their stock pretty regularly, so I’m probably due to go back & check it out! (I am kinda loving this psychedelic flower one!)

You can find some cool painted options on Etsy, too. Belle Helmets do hand-painted helmets — I especially like this tarot card one!

If you already have a helmet, but you’re looking to jazz it up, decoupage it! (Thanks, Kayla!)

Oh, & if you REALLY want to stand out, how about this bunnyhead helmet?! (Amazing.)

Got helmet hair? My solution to helmet hair has been to carry around a scarf or a little knit hat in my satchel. When you hop off, you can just tie the scarf around your head, or slip a beanie on for instant, simple “done-ness”!

On skirts, dresses & preserving one’s modesty

I love, love, love to wear dresses or skirts on the bike. I don’t really wear pants in my daily life, so why would I wear them when I cycle?!

If you, like me, want to rock vintage dresses on your bike, I think the best skirt shapes are knee-length A-line, & the top of the dress can’t be too tight. If your dress is very form-fitting around the shoulders & upper arms, you run the risk of ripping it open while you perform some kind of daredevil manoeuvre! You also don’t want a crazy long skirt, because it can catch on your bike — though you can always pull it up & tie it in a knot in your lap while you ride! If you’re still worried though, you can always DIY your own skirtguards!

Of course, the major issue with wearing a skirt or dress on a bicycle is that you run the risk of flashing innocent passersby. This is to be avoided if at all possible. No one wants to see your knickers, no matter how fancy they may be, & a little mystery is worth preserving. But don’t fret! I have a solution! BLOOMERS!

Where else could cute handmade bloomers be found but Etsy?! (It’s a no-brainer, really!) My favourites are black & white striped, these magenta ruffly ones from the 1930s (though honestly, too good to wear underneath anything!), black & white stars (I own a pair of these!), & these Victorian-inspired black bloomers. So cute.

I also discovered that American Apparel makes GREAT bloomers, which are actually quite flattering on (even though you wouldn’t think it from the photos they use!). I got a pair of the purple cotton seersucker bloomers & honestly, I don’t want to take them off… ever. Yes, you can be (relatively) modest & stylish at the same time! Let’s boogie!

On satchels, handbags & baskets

The type of bag you carry on a bicycle will really be determined by whether your bike has a basket on it or not. Mine has a sweet little wicker basket, which I adore — great for just throwing things into. It also means you can take any kind of handbag you please.

If you’re basketless, your best option is a satchel or anything with a long strap. You can hang it diagonally across your body, & it will essentially be out of your way while you’re pedalling. I have approximately 10,000 satchels but this raspberry metallic satchel from the Cambridge Satchel Company is reigniting my love for them all over again! I also love it in patent yellow, fluoro lime green & metallic gold! Zatchels, who are — from what I can see — Cambridge Satchel Company’s main competitor, do the exact same bags with a variety of patterns. I like the floral print, black & white polka-dot, & reptile print! (They have a lot of other options too — have a look.)

Another good choice is a backpack. This simple wool backpack is cute in an understated, minimal kinda way, while this spring floral backpack is totally on the opposite end of the spectrum! I’m a fan of this LeSportSac x Joyrich leopard-print backpack, & this one is so simple & chic.

On practicality, & riding in high heels

Practicality is overrated! I don’t believe in riding in so-called “sensible shoes”. Maybe this is because I don’t own any, maybe it’s because I have a crazy deathwish, or maybe it’s just because I am contrary. Whatever the case, don’t be afraid of riding in heels! It can be done!

In fact, I’ve found that it is no trouble at all to ride in heels. I can give my personal stamp (ha ha, ho ho) of approval to the Sam Edelman Zoe (as seen above!) & Irregular Choice’s Tea & Cakes shoe! I’ve also ridden in sparkly Converse (yep, of course this works perfectly) & Dr Marten boots with heels. My everyday boots — the Frye Carmen Harness Short — are fab on a bike too. (I absolutely love them. Favourite boots EVER!)

Mostly, the key is to have a heel which you can hook over the back of the pedal. Wedges are tricky, simply because the surface is totally flat & you can’t really feel what you’re doing. Avoid wedges!

I have to admit, though, I haven’t tried cycling in my fetishy polka-dot Mary Janes, or my pink sparkly Louboutins. Well, even I have limits!

On riding around the icy tundra (or, the winter-times)

When the temperatures start to drop, the temptation is to bundle up, hail a taxi & let your bicycle collect cobwebs. The truth is, you can ride your bike almost the whole year, if you’re dressed appropriately!

Here are some items I suggest in your keeping-warm-on-the-bike arsenal…

Leather leggings
A thick scarf you can pull up over your mouth
Cashmere-lined leather gloves, or something equally decadent & cozy. P.S. I like to buy gloves from places like Century 21 or T.J. Maxx, they always have great deals!
Cashmere leggings
Merino wool layering pieces , like sweaters, turtlenecks & long tunics to keep your lower back covered!
A cute blazer (love that one, so Willy Wonka!) or jacket
A faux fur gilet
Riyoko have fleece-lined leggings in cute patterns!

Really, the trick is to wear super-warm layers. They don’t have to be thick & bulky. I love merino wool & Uniqlo’s HeatTech pieces for this purpose — they’re the thickness of a regular t-shirt but keep you really toasty. If you can keep your torso warm, you won’t need to wear a trillion layers & look like the Stay-Puft Marshmallow Man! Hooray!

You also don’t have to go out & buy all new things just to ride on your bike! One of my favourite blazers is an old velvet thing, it’s got tattered sleeves but I love it for topping off a cycling ensemble!

You might also want to check some of those shops for outdoorsy, adventure type people. I don’t really know what they’re called! However, they’re great for stocking up on thermal underthings, stuff made of Thinsulate, really warm hats, scarves, gloves, etc. They also often have “athletic” sections, so you might even find stuff made specifically for intrepid winter biking!

P.S. I love the Winter B-Icicle Challenge! We can do it!!!

On lovely extras & fancy accessories

When I went for my first official ride — i.e., not the time I rode it home from the shop — I rode up & down the East River Promenade. It’s quite lovely over there. There were lots of other people on bikes, too, & one who stood out to me. She was wearing a massive oversized black floppy hat, & a leather motorcycle jacket covered in spikes. She looked amazing, & grinned at me as we passed one another.

There are so many ways to look great on a bike. If you’re in search of some inspiration, Copenhagen Cycle Chic — & its international counterparts New York Cycle Chic, Paris Cycle Chic, London Cycle Chic, etc. — are good places to start. CCC have a great motto which is that anything you wear to walk around in, you can cycle in. So true! There’s also a guide to riding in winter, if you’re still anxious about doing so!

The internet is dangerous, though. The more I look around, the more cute bike-related stuff I find! I love this t-shirt: I cycle NY!

This bowler hat helmet is fabulous, but the cost is prohibitive, to say the least. I’m sure someone clever could DIY their own!

These women’s riding pants look pretty much perfect, too. I wish they had more sizes, though! What’s up with that?! Actually, pretty much everything in the Outlier shop is gorgeous.

When it comes to locking your bike up, if you live in a city like New York, you can’t mess around. I picked up a Kryptonite New York Fahgettaboutit Mini Bicycle U-Lock (ha! “Fahgettaboutit!”), & it has done the trick. A lot of cyclists in Manhattan ride around wearing enormous chains, which they later use to lock their bicycles up. (Do you remember when The Sartorialist thought bike chains as accessories should be the next big thing?!)

I love this idea, too: Catherine Strassman has created reflective scarves for cyclists. You can buy them here! Genius, right?!

If you need extra inspiration…

Check out this DIY polka-dot helmet! (A big YES to that!) Here’s a piece on cycling & self-esteem, as well as some DIY bike decorating tips from Let’s Go Ride A Bike. If you’re in NYC, you might appreciate Ride The City which plots the safest — & most efficient — bike paths. Rides A Bike is a cool collection of pictures of awesome people cycling, &
this is a modern take on the idea. If you look at Fashionising’s bicycle tag, you’ll see a bunch of good-looking people making cycling look fab, too!

Real people on real bicycles…

Of course, now I’m dying to go for a ride! Won’t you join me?!

Photos by Lydia Hudgens!