Crossbody bags are like the little black dress of the handbag world. They're more practical and versatile than any other silhouette, and chances are you and all your friends each have one. There's just one — or, erm... two — things that can get in the way, and they're called your boobs.
Anyone who's shopped long and hard for the perfect crossbody or worn one for any length of time knows that when they're good, they're really good, and when they're uncomfortable, they can make you question all of the purse-buying choices that led you to this moment. If you've ever lugged around a too-heavy bag, you know what we're talking about: One sore shoulder, a bruise-blister-hybrid where the buckle's been rubbing all day, and a lumpy, bumpy, frankly unflattering situation where the strap crosses your chest and causes your shirt to wrinkle up.
The right crossbody, though, will not only suit your personality, but it'll fit you well, too. And, sure, maybe this isn't a fit that's quite as important as the bra you're wearing underneath, but we've found the style that will work flawlessly for you and your cup size. Strap one on, ahead.
Full & Round: Chain-Strap Crossbody
Having some cushion may help if you want to try a typically not-too-comfortable chain strap. The style is hefty and bold enough to not get totally lost in your cleavage, but still provides a nice bit of separation for those days when you feel like you're rocking a uni-boob.
Mango Chain Leather Bag, $59.99, available at Mango.
If you're not totally fond of metal chains, this dual-texture piece offers the same effect with some added comfort by way of a leather shoulder strap.
Anya Hindmarch Chain Strap Crossbody Bag, $1,925.64 $962.82, available at Farfetch.
When looking for a bag, any old chain won't do. Go big or go home with some oversized links and studs galore.
Zara Studded Bucket Bag, $49.90, available at Zara.
East-West, Conical, Or Uneven: Thin-Strap Crossbody
For boobs that veer in opposite directions or are two different sizes, a thick strap might sit on your chest uncomfortably. Instead, stick with an option that's on the thinner side, allowing it to rest more naturally and feel less intrusive (and while you're at it, find the perfect everyday bra, too).
Chloe Faye Mini Crossbody Bag, $1,290, available at Neiman Marcus.
J.Crew's new customizable bags are a great blank canvas for making your ideal crossbody.
J.Crew Signet Bag in Italian Leather, $128, available at J.Crew.
Keep things minimal with a cement-colored bag that will go with every single thing in your closet.
Silence + Noise Roll Clutch Crossbody Bag, $39, available at Urban Outfitters.
Petite & Perky, Or Shallow: Wide-Strap Crossbody
Super-wide straps are one of those trends that seems really awesome, but in practice, don't really work. These types of bags tend to sit more comfortably on smaller or flatter chests, since it's likely to lay flatter (whereas it might squeeze and squish larger breasts). But if you find a wide strap feels like it’s smashing your small chest, too, a delicate, thin one is, of course, fair game.
3.1 Phillip Lim Alix Mini Crossbody, $895, available at 3.1 Phillip Lim.
If you can swing it, you won't regret splurging on the epitome of this trend — you can see the oversized strap on Burberry's mix-and-matched variation from a mile away.
Burberry The Patchwork in Textured Suede & Leopard-print Calfskin, $2,495, available at Burberry.
Keep things sporty and casual with this athleisure take on the wide-strap crossbody — yep, the '90s are alive and well with this Fila number.
Fila Foster Small Crossbody Bag, $42, available at Pacsun.
Mind The Gap: Comfort-Strap Crossbody
With a large space between your two breasts (a.k.a. built-in cushioning) you may want to avoid big buckles or anything else that could dig into your chest bones. A not-too-thin, not-too-wide strap is always a safe pick.
Loeffler Randall Saddle Crossbody, $395, available at Need Supply.
A fabric strap is sure to stay comfortable for longtime wear, which means you can go from work to happy hour without dreading wearing a bag that isn't.
Lotfi Canteen Bag, $107, available at Lisa Says Gah.
Suede is another solid bet, and you generally can't go wrong with a spacious bucket bag.
Christy Dawn The Sophia Bucket, $399, available at Christy Dawn.
Narrow, Slender, Or Bottom-Heavy: Adjustable Support Strap
Did you know your crossbody strap could double as a support mechanism to lift and separate? Wide, easy-to-wear straps are also key here, but the more important element is adjustability, so you can wear it snug and high across your chest, allowing for the desired amount of lift.
Leau Products Leau Bag Light Blue, $198, available at W Concept.
Removable straps are an added bonus across the board. With a customizable bag, you can use it as a crossbody during the day, and as a clutch come nighttime.
H&M Small Shoulder Bag, $59.99, available at H&M.
Let this signature Gucci color combo brighten up a jeans-and-a-tee look.
Gucci Lady Web Medium Crossbody Bag, $2,700, available at Neiman Marcus.
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