The challenge is simple. Pack enough to look stylish and avoid wearing similar variations of a uniform, but not so much that you can’t fit it all into a carry-on. Oh, and to only do laundry once a week. This guide works well for warm-weather destinations where you’ll be sight-seeing (walking tons), swimming (or sunbathing), visiting religious houses (where modesty is an issue), transitioning from super-hot to air conditioned throughout the day, and indulging in swanky evening activities that require you to be dressy. You’ll also see tips on how to make adjustments for cruising, work-related trips, and more tropical destinations that are short on air conditioning.
CHOOSE A COLOR PALETTE
Instead of assembling individual outfits, think instead of packing a collection – with pieces able to mix-and-match to perfection. Building a foundation of neutrals will allow for maximum mix-ability. For my neutrals, I chose:
- White (1 top + 1 bottom + complimentary top in black)
- Beige (1 top + 1 bottom + complimentary bottom in leopard print)
- Navy (1 top + 1 bottom + complimentary top in chambray)
- Tan (1 jacket)
- Black (1 LBD)
Other neutral options are Grey and Brown. Each foundation neutral color you choose should compliment the others in your set. An example of two neutrals that aren’t ideal together: Black + Navy, or Grey + Beige.
You’ll then need to add your non-neutral color(s) into the mix. Keep in mind that any foundation colors you choose should have a 1 top and 1 bottom in that color, as well as another complimentary item. My final foundation color is Sea Glass, which looks fabulous with any of the foundation neutrals in my set.
- Sea Glass (1 top + 1 bottom + complimentary topper in tropical green)
- Kelly Green (1 accent top)
- Emerald Green (1 dress)
The Breakdown - (Here’s what I have in my list):
- 2 Toppers (1 Jacket, 1 Cardigan)
- 7 Tops (3 Tanks, 1 Tshirt, 2 Blouses, 1 Sweater)
- 5 Bottoms (1 Shorts, 1 Skirt, 1 Pants, 2 Crops)
- 2 Dresses (1 LBD, 1 Statement Dress)
- 2 Scarves (1 colorful & gauzy, 1 solid & warm)
- 5 Shoes (2 heels, 3 flats)
- 1 Belt
- 1 Purse
- 1 Swimsuit (pack 2 if you’re a real beach bum)
- 1 Hat
- 1 Pair of Sunglasses
- Jewelry (3 Necklaces, 1 Bracelet, 1 Watch, 1 Ring, 4 Pairs Statement Earrings, 4 Pairs Stud Earrings)
1. NEUTRAL JACKET
Pack a lightweight jacket in a neutral color (like tan), that will pair well with all the pieces in your set. Go for a classic, fitted silhouette. In addition to extra warmth on cool days, your jacket should protect you from the most likely worst-case-scenario (usually rain and/or wind). It will also add variety to your topper options, and can be styled with the sleeves pushed up for a more casual look. If you’ll be traveling for work, I also recommend bringing a blazer.
Trench Coat: Jack Wills (Discontinued)
2. LITTLE BLACK DRESS
If you could only pack one thing, an LBD is the top priority. Choose one that can be formal enough for an elegant dinner, sexy enough for a night on the town, easy enough for a day at the beach, and lightweight and wrinkle-free, while we’re at it. Choose topper options that will complement your LBD. If your dress is short enough, you might be able to style it as a tunic – if so, make sure it will wear well with at least one pair of bottoms.
Little Black Dress: White House | Black Market (Discontinued)
3. TANK TOP
A tank top is a great staple for layering, and can be a comfortable option to wear on it’s own in hot weather. Look for a tank with wide straps and be sure to pack a bra that won’t show through.
White Tank: White House | Black Market (Discontinued)
4. DRESSY SHELL OR BLOUSE
Another layering must-have, a dressy shell can be a sexy statement by itself, or can look quite polished when worn with a topper. This one has a built-in-bra, so peek-a-boo bra straps become a non-issue. Otherwise, opt for one with wide straps.
Black Shell: White House | Black Market
5. LIGHT TROUSERS
I usually stick with slim-fit pants when traveling (to avoid being required to wear a certain height shoe), but I couldn’t resist these wide-leg trousers. If you do decide on a pair of pants that require you to wear high-heels, be sure they are hemmed to the correct height for the shoes you’re packing. If you pack more than one pair of high-heeled shoes, make sure they are all close to the same height (3 inches is a good limit). You might also bring fashion tape along to hem-up your pants if you just can’t bring yourself to wear high heels. Sometimes comfort just wins out. (This tip requires the use of an iron so you can make a crease at the hem – most hotels will have one for you.)
White Wide-Leg Pants: Express
6. T-SHIRT OR BLOUSE
Choose a blouse (this one has metallic embroidery and studs to dress it up) that will match any of the bottom options you pack. Solid colors work well here, but if you can find a subtle pattern with colors that will tie in several pieces, even better. Keep in mind the more tops you bring with sleeves, the longer your ‘toppers’ can go between washings (read: if your pits are exposed to your cardigan, it’s gonna’ get stinky). Other benefits to sleeves: you’ll be more comfortable when you want to skip a topper, but need your shoulders covered for modesty (like in a cathedral or other religious setting); they keep your shoulders protected from your heavy day-pack strap(s); and allow for more bra options.
Metallic Beige T: White House | Black Market
A neutral or patterned short that can tie in the colors of several tops will be the perfect choice. Try to find a pair that look great with your swim-suit. I generally suggest a 7 inch inseam or longer, both for modesty and comfort (I mostly just don’t want my bum-cheeks touching seats on the subway… I try to keep it classy like that). If you’re traveling for business, switch the shorts out for a pencil skirt.
Leopard Print Shorts: White House | Black Market
8. SLIM PANTS
Slim-fit, Straight legged, or Crops can all work well here. For summer, I like to keep the color light. Slim-fit pants have the benefit of looking great with flat shoes or high heels, without the drawback of dragging in the dirt when you’re wearing those flats. Plus, they also allow for you to fold up the hem at various lengths, to give you some variety. I don’t find skin-tight-to-the-ankle to be quite as universally flattering as a semi-straight fit, but tall, slim girls can pull either off quite nicely. Look for a pair that won’t wrinkle terribly, which can be very noticeable on light colors.
Beige Cropped Pants: White House | Black Market
9. SUMMER WEIGHT SWEATER
Pack a light-weight sweater with a different neckline than the majority of your tops, simply for variety’s sake. This also allows you the option to dramatically change the way another top looks when paired over or under the sweater. Avoid anything itchy, and try to pick one you’ll be able to launder easily.
If your destination is more tropical and less air-conditioned, switch this out with a comfortable blouse or t-shirt. Keep in mind that cruises and business trips will both involve quite a lot of AC, so even if the destination is warm, you might be surprised at how often you get cold.
Navy Sweater: J.Crew
10. CHAMBRAY SHIRT
A button-down-shirt in chambray is a great layering piece that can be worn over or even under many of the other items in your set. A perfect not-too-hot option when you’ve got to have sleeves (like in a church) or get a little chilled. It can also moonlight as a top on its own.
Chambray Shirt: White House | Black Market
11. DARK-WASH JEANS
Dark wash jeans can be dressed up or down, and look more polished than regular-washed denim. (A plus when dining at anti-jean-dress-code restaurants). As a concession to our warm-weather destination, I’ve decided to go for capri length here. Since we’re only packing 5 options for bottoms, I like to keep the colors, silhouettes and lengths different for every piece.
Cropped Skinny Jeans: White House | Black Market
12. FLOWY BUTTON-DOWN BLOUSE
An unstructured button-down top that is light and breezy has the same benefits as your chambray shirt, in that it can be worn as a top or a topper, and has tons of versatility. I opted for mine to be in an accent color, and it pairs well with all my foundation colors.
Portofino Shirt: Express
13. CAMISOLE – POP OF COLOR
Since we’re already packing 2 other sleeveless options, try to mix up the neck-line for variety. Pick one that has a built-in bra or go for a tank-style top with wider straps so bra straps won’t show.
Sea Glass Cami: White House | Black Market
14. CARDIGAN – SOLID COLOR
A cardigan in an accent color is a great way to bring some color to your packing list. I like to pack my cardigan in my day pack (assuming I’m not already wearing it) to allow for layering adjustments as I transition from indoors, to outdoors, to public transportation, etc.
When choosing your skirt, try to keep in mind the style of the dress you’ve already packed. Go for a different silhouette, color(s), texture, and possibly even length. If my trip was business-oriented, I would go with a pencil skirt for more structure.
Full Skirt: Victoria’s Secret
16. STATEMENT DRESS
Think of your travel activities before packing your second dress. Choose a hot number that can transition well from day to night, but with a different silhouette than your LBD. If you opt for a maxi dress, be conscious of the length and the height of your shoes to ensure you won’t be dragging your hem through the streets.
Scarves can completely change an outfit, and are incredibly versatile. Need some extra warmth? Check. Need a pillow? Check. Bad hair day? Swimsuit coverup? On and on this list could go. Plus, they’re very European. What’s not to love about that? Be sure to pick scarves that will pair well with virtually every outfit combination. I like to pack a colorful, gauzy one, and a solid wrap-style scarf for warmth adjustments.
Shoes. So, so critical. I suggest a pair of comfortable sandals, ballet flats (I am in love with Cole Haan’s Air Bacaras, which have Nike Air technology for supreme comfort), and a good pair of walking shoes like sneakers, loafers or oxfords. Bonus points if your shoes compliment your purse/day bag. If you’re traveling for business or going on a cruise, add one pair of heels. If any clothing items require heels (as the trousers in this set), maybe two. They should be comfortable, match everything, have good traction, and be light weight. Try to avoid similar styles (example 2 pairs of t-straps) in case any blisters start to form and you need a break from that style.
Make sure to break-in any shoes you’ll be taking, and try the following exercise with each pair: Wear them to the mall/grocery store/office. Walk around for 6 hours, or as long as possible with no sitting. Then decide if you still want to bring those shoes.
Jewelry should be made up of mostly neutrals that can be worn with everything in your set. I always look for pieces that can be worn at least 2 ways. The first necklace in this set is a long string of faceted green beads. They can be worn looped around my neck two or three times, or tied in a knot and left long. The crystal necklace (from J.Crew) can be adjusted for length, and worn reversed so the back (gold) side is showing. It can also be layered with the pearl necklace (also from J.Crew). The pearls can be worn loose or twisted. The more twisting you do, the shorter the necklace becomes. The bracelet pairs well with both the crystal necklace or the pearl one, and works with any of my earring options.
The earrings include gold, silver, sea glass, pearls, and emerald. Pack small studs as well as statement earrings. Avoid anything heavy.
Other everyday essentials are a watch, wedding ring, hat, sunglasses and belt. These all need to match with every other item you pack, since you’ll be using them more than any other item. Ditto your purse/day bag.
For underwear, I usually pack briefs in nude and black, and one thong in each. Choose bras that lay well under all your tops, one nude and one black. A comfortable sports bra is a good idea, as well.
Don’t forget Jammies. I usually pack a pair of leggings or yoga pants and a comfy t-shirt. If you’re a runner, these can double as workout gear as well. Speaking of which, be sure to pack running shoes and several pairs of socks if you’re going to be working out. (Do you work out already? If not, don’t think that suddenly you’ll become a fitness guru while you’re traveling. You won’t. Don’t pack something if you don’t currently use the hell out of it.)