I’m a big advocate for people wearing whatever they are most comfortable in, especially while on vacation or traveling in general. Everyone has their personal preference, and while some of us are more than willing to sacrifice a bit of function for the sake of fashion, there are definitely a few “won’t wears” I have for travel style. Here’s a rundown of the wills and won’ts of travel and vacation outfitting.
Most of my travel takes place in the warmer months; however, over the holidays, we are either road tripping or flying to be with family. No matter the time of year, it’s best to avoid bulky outerwear if you can help it. However, even in summer, a light jacket is usually needed. I tend to don a denim version for family trips, or a linen blazer if I find myself on work-related travel. A lightweight denim piece like Levi’s Tini Long-Sleeve Utility Shirt is an easy go-to layer and can create casual looks by wearing it with all sorts of outfits, from my joggers to dresses. A linen blazer, such as Loft’s Oversized Linen Blend Modern Blazer, makes for a great travel staple when choosing one in a neutral shade to coordinate with multiple looks.
Another denim item that is a “won’t” for traveling is skinny jeans. In fact, I haven’t personally worn skinny jeans in over a year, but I’m hanging on to them because denim trends are cyclical. For now, and for vacation, relaxed jeans are your best fit. They can be flared or straight-leg, nice enough to wear for going out, yet comfortable enough for a long car trip. Quince’s Bella Stretch Relaxed Straight Jeans have a simple shape and kind of give off a ’90s vibe, which was a decade with some memorable summers for sure! Also pack along a pair of leggings, if you’re planning any exercise or active activities, and a pair of joggers. Gap Factory’s Mid Rise Pull-On Soft Barrel Jeans are an ideal mix of both jean and jogger with their drawstring waist and soft denim. You can wear these for walking around the amusement park or lounging by the fire. Full disclosure, they were on sale as of this writing, and I just added to my cart!
From bottoms to tops. It can be difficult to pack and plan tops for travel. On one hand, you want to wear cute things on vacation, like silk tanks and going-out blouses. On the other hand, wrinkling, potentially spilling, or leaving it behind accidentally makes me more often than not leave my nicest pieces at home and opt for plain white tees, tanks, and shirts. I recently discovered Mott & Bow’s Fitted V-Neck Marcy Tee that you can buy as a single shirt or in packs of 3 to 6. The product description highlights their fabric blend of pima cotton and modal for a lightweight, breathable feel. Sounds like the perfect textile for traveling in my book. For a button-down for summer, it is best to go with linen if you can, like Old Navy’s Linen-Blend Loose-Button Shirt. Wear this with jeans, with skirts, or even as a poolside cover-up.
For footwear, while I love my bright, colorful sneakers and a strappy sandal, I keep them at home when vacationing, preferring instead more neutral kicks and a simple slide. Slides are easier to pack and quite versatile. You can wear a classic, like Birkenstock Siena Big Buckle sandal with denim during the day and a dress in the evening. With any shoe, you want to be able to wear it with multiple looks instead of hauling around a bunch of pairs that only go with certain outfits. The best travel shoes are neutral and also supportive/comfortable.
As for accessories, unless there’s a special occasion, like a wedding, I keep jewelry very simple. Usually, the pieces I wear while in actual route are the ones and only ones I’ll wear throughout the trip. One watch, a few rings, maybe a cuff bracelet, a necklace or two, and a pair of sunglasses. Again, I’d wear all of these, plus a baseball hat, in the car, plane, bus, etc. Of course, if you are going to be seaside, it’s smart to also pack a sunhat and maybe an extra pair of sunnies.
When you put all of these “will wears” together, denim jacket, barrel jean joggers, white tee, sneakers, you have a standard, yet sleek traveling outfit. In general, you will want to pack and wear versatile pieces, items you can layer, and comfortable shoes. Of course, you may want to include a few statement pieces, and I’m never one to deny a person an outrageously printed kaftan on vacation.


